Amino acid-derived heterocycles as combinatorial library targets: Bicyclic aminal lactones

Journal of Combinatorial Chemistry

Volumn 5, Issue 3, 2003, Pages 278-284

  Lewis, Jason G ^a   Bartlett, Paul A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; AMINO ACID DERIVATIVE; ESTER DERIVATIVE; HETEROCYCLIC COMPOUND; LACTONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; COMBINATORIAL LIBRARY; CYCLIZATION; ISOMER; SOLID; STEREOSPECIFICITY; SYNTHESIS;

ALKYLATION; AMINO ACIDS; ANIMALS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; LACTONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 0141521864     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc020082i     Document Type: Article

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18. For related work see: Marx, M. A.; Grillot, A.-L.; Louer, C. T.; Beaver, K. A.; Bartlett, P. A. J. Am. Chem. Soc. 1997, 119, 6153-6167. Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. Todd, M. H.; Ndubaku, C.; Bartlett, P. A. J. Org. Chem. 2002, 67, 3985-3988. Spaller, M. R.; Thielemann, W.; Brennan, P. E.; Bartlett, P. A. J. Comb. Chem. 2002, 4, in press. Trump, R. P.; Bartlett, P. A. J. Comb. Chem. 2002, 5, 285-291.
19. For related work see: Marx, M. A.; Grillot, A.-L.; Louer, C. T.; Beaver, K. A.; Bartlett, P. A. J. Am. Chem. Soc. 1997, 119, 6153-6167. Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. Todd, M. H.; Ndubaku, C.; Bartlett, P. A. J. Org. Chem. 2002, 67, 3985-3988. Spaller, M. R.; Thielemann, W.; Brennan, P. E.; Bartlett, P. A. J. Comb. Chem. 2002, 4, in press. Trump, R. P.; Bartlett, P. A. J. Comb. Chem. 2002, 5, 285-291.
20. For related work see: Marx, M. A.; Grillot, A.-L.; Louer, C. T.; Beaver, K. A.; Bartlett, P. A. J. Am. Chem. Soc. 1997, 119, 6153-6167. Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. Todd, M. H.; Ndubaku, C.; Bartlett, P. A. J. Org. Chem. 2002, 67, 3985-3988. Spaller, M. R.; Thielemann, W.; Brennan, P. E.; Bartlett, P. A. J. Comb. Chem. 2002, 4, in press. Trump, R. P.; Bartlett, P. A. J. Comb. Chem. 2002, 5, 285-291.
21. For a recent, comprehensive review, see: Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825-1872.
22. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
23. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
24. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
25. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
26. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
27. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
28. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
29. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
30. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
31. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
32. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
33. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
34. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
35. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
36. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
37. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
38. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
39. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
40. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
41. Examples of peptide acetals represented in Figure 1:1 (n = 1, X = N): Vojkovsky, T.' Weichsel, A.; Patek, M. J. Org. Chem. 1998, 63, 3162-3163. 1 (n = 2, X = N): Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205. 1 (n = 1, 2, X = O): Smith, L. R.; Bartlett, P. A. Mol. Online 1998, 2, 58-62. 1 (n = 2, X = S): Kohn, W. D.; Zhang, L. Tetrahedron Lett. 2001, 42, 4453-4457. 2 (n = 1, X = S): Refouvelet, B.; Robert, J. F.; Couquelet, J.; Tronche, P. J. Heterocycl. Chem. 1994, 31, 77-80. 4 (m = n = 1, X = N): Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-6992. 4 (m = 2, n = 1, X = O): Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936. Zhang, X.; Jiang, W.; Schmitt, A. C. Tetrahedron Lett. 2001, 42, 4943-4945. Slomczynska, U.; Chalmers, D. K.; Cornille, F.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Org. Chem. 1996, 61, 1198-1204. 4 (m = 2, n = 1, X = S): Flammang, M.; Gasquez, F.; Kimny, T.; Compagnon, P. L. Compt. Rend. Acad. Sci., Ser. II 1991, 312, 989-992. 4 (m = 2, n = 2, X = S),4(m = 3, n = 1, X = O, S): Robl, J. A.; Sun, C.-Q.; Stevenson, J. ; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. J. Med. Chem. 1997, 40, 1570-1577. 4 (m = 3, n = 1, X = O): Slomczynska, U.; et al. J. Org. Chem. 1996, 61, 1198-1204. 5 (m = n = 1, X = O, S): Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148. (m = n = 1, X = O): Baldwin, J. E.; Freeman, R. T.; Hulme, C. Tetrahedron Lett. 1989, 30, 4019-4020. 5 (m = n = 1, X = S): Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K. ; Johnson, R. L. J. Med. Chem. 1999, 42, 2977-2987. 5 (m = 1, n = 2, X = O): Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992-6999. (m = 1, n = 2, X = S): Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650. 5 (m = 1, n = 3, X = S): Akasaka, K.; Komatsu, Y.; Tagami, K.; Shimizu, T.; Shimomura, N.; Naka, H.; Hayashi, K.; Negi, S. Chem. Pharm. Bull. 1999, 47, 1532-1537.5 (m = 2, n = 1, X = S): Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1999, 42, 628-637.
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