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Volumn 64, Issue 9, 1999, Pages 3312-3321

Use of steric interactions to control peptide turn geometry. Synthesis of type VI β-turn mimics with 5-tert-butylproline

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; GEOMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; X RAY DIFFRACTION;

EID: 0033617257     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990294a     Document Type: Article
Times cited : (96)

References (109)
  • 1
    • 0024279235 scopus 로고
    • Reviews and leading articles on β-turns include the following: (a) Wilmot, C. M.; Thornton, J. M. J. Mol. Biol. 1988, 203, 221. (b) Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv. Protein Chem. 1985, 37, 1. (c) Richardson, J. S. Adv. Protein Chem. 1981, 34, 167. (d) Lewis, P. N.; Momany, F. A.; Scheraga, H. A. Biochim. Biophys. Acta 1973, 303, 211. (e) Venkatachalam, C. M. Biopolymers 1968, 6, 1425.
    • (1988) J. Mol. Biol. , vol.203 , pp. 221
    • Wilmot, C.M.1    Thornton, J.M.2
  • 2
    • 0021779081 scopus 로고
    • Reviews and leading articles on β-turns include the following: (a) Wilmot, C. M.; Thornton, J. M. J. Mol. Biol. 1988, 203, 221. (b) Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv. Protein Chem. 1985, 37, 1. (c) Richardson, J. S. Adv. Protein Chem. 1981, 34, 167. (d) Lewis, P. N.; Momany, F. A.; Scheraga, H. A. Biochim. Biophys. Acta 1973, 303, 211. (e) Venkatachalam, C. M. Biopolymers 1968, 6, 1425.
    • (1985) Adv. Protein Chem. , vol.37 , pp. 1
    • Rose, G.D.1    Gierasch, L.M.2    Smith, J.A.3
  • 3
    • 0019443447 scopus 로고
    • Reviews and leading articles on β-turns include the following: (a) Wilmot, C. M.; Thornton, J. M. J. Mol. Biol. 1988, 203, 221. (b) Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv. Protein Chem. 1985, 37, 1. (c) Richardson, J. S. Adv. Protein Chem. 1981, 34, 167. (d) Lewis, P. N.; Momany, F. A.; Scheraga, H. A. Biochim. Biophys. Acta 1973, 303, 211. (e) Venkatachalam, C. M. Biopolymers 1968, 6, 1425.
    • (1981) Adv. Protein Chem. , vol.34 , pp. 167
    • Richardson, J.S.1
  • 4
    • 0015930720 scopus 로고
    • Reviews and leading articles on β-turns include the following: (a) Wilmot, C. M.; Thornton, J. M. J. Mol. Biol. 1988, 203, 221. (b) Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv. Protein Chem. 1985, 37, 1. (c) Richardson, J. S. Adv. Protein Chem. 1981, 34, 167. (d) Lewis, P. N.; Momany, F. A.; Scheraga, H. A. Biochim. Biophys. Acta 1973, 303, 211. (e) Venkatachalam, C. M. Biopolymers 1968, 6, 1425.
    • (1973) Biochim. Biophys. Acta , vol.303 , pp. 211
    • Lewis, P.N.1    Momany, F.A.2    Scheraga, H.A.3
  • 5
    • 0014347799 scopus 로고
    • Reviews and leading articles on β-turns include the following: (a) Wilmot, C. M.; Thornton, J. M. J. Mol. Biol. 1988, 203, 221. (b) Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv. Protein Chem. 1985, 37, 1. (c) Richardson, J. S. Adv. Protein Chem. 1981, 34, 167. (d) Lewis, P. N.; Momany, F. A.; Scheraga, H. A. Biochim. Biophys. Acta 1973, 303, 211. (e) Venkatachalam, C. M. Biopolymers 1968, 6, 1425.
    • (1968) Biopolymers , vol.6 , pp. 1425
    • Venkatachalam, C.M.1
  • 7
  • 8
    • 0032503564 scopus 로고    scopus 로고
    • Examples include: (a) Takeuchi, Y.; Marshall, G. R. J. Am. Chem. Soc. 1998, 120, 5363. (b) Baures, P. W.; Ojala, W. H.; Gleason, W. B.; Johnson, R. L. J. Pept. Res. 1997, 50, 1. (c) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1996, 61, 9437. (d) Chalmers, D. K.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 5927. (e) Genin, M. J.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1993, 36, 3481. (f) Hinds, M. G.; Welsh, J. H.; Brennand, D. M.; Fisher, J.; Glennie, M. J.; Richards, N. G. J.; Turner, D. L.; Robinson, J. A. J. Med. Chem. 1991, 34, 1777.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5363
    • Takeuchi, Y.1    Marshall, G.R.2
  • 9
    • 0030738499 scopus 로고    scopus 로고
    • Examples include: (a) Takeuchi, Y.; Marshall, G. R. J. Am. Chem. Soc. 1998, 120, 5363. (b) Baures, P. W.; Ojala, W. H.; Gleason, W. B.; Johnson, R. L. J. Pept. Res. 1997, 50, 1. (c) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1996, 61, 9437. (d) Chalmers, D. K.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 5927. (e) Genin, M. J.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1993, 36, 3481. (f) Hinds, M. G.; Welsh, J. H.; Brennand, D. M.; Fisher, J.; Glennie, M. J.; Richards, N. G. J.; Turner, D. L.; Robinson, J. A. J. Med. Chem. 1991, 34, 1777.
    • (1997) J. Pept. Res. , vol.50 , pp. 1
    • Baures, P.W.1    Ojala, W.H.2    Gleason, W.B.3    Johnson, R.L.4
  • 10
    • 0030446803 scopus 로고    scopus 로고
    • Examples include: (a) Takeuchi, Y.; Marshall, G. R. J. Am. Chem. Soc. 1998, 120, 5363. (b) Baures, P. W.; Ojala, W. H.; Gleason, W. B.; Johnson, R. L. J. Pept. Res. 1997, 50, 1. (c) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1996, 61, 9437. (d) Chalmers, D. K.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 5927. (e) Genin, M. J.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1993, 36, 3481. (f) Hinds, M. G.; Welsh, J. H.; Brennand, D. M.; Fisher, J.; Glennie, M. J.; Richards, N. G. J.; Turner, D. L.; Robinson, J. A. J. Med. Chem. 1991, 34, 1777.
    • (1996) J. Org. Chem. , vol.61 , pp. 9437
    • Lombart, H.-G.1    Lubell, W.D.2
  • 11
    • 0000325130 scopus 로고
    • Examples include: (a) Takeuchi, Y.; Marshall, G. R. J. Am. Chem. Soc. 1998, 120, 5363. (b) Baures, P. W.; Ojala, W. H.; Gleason, W. B.; Johnson, R. L. J. Pept. Res. 1997, 50, 1. (c) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1996, 61, 9437. (d) Chalmers, D. K.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 5927. (e) Genin, M. J.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1993, 36, 3481. (f) Hinds, M. G.; Welsh, J. H.; Brennand, D. M.; Fisher, J.; Glennie, M. J.; Richards, N. G. J.; Turner, D. L.; Robinson, J. A. J. Med. Chem. 1991, 34, 1777.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 5927
    • Chalmers, D.K.1    Marshall, G.R.2
  • 12
    • 0027431171 scopus 로고
    • Examples include: (a) Takeuchi, Y.; Marshall, G. R. J. Am. Chem. Soc. 1998, 120, 5363. (b) Baures, P. W.; Ojala, W. H.; Gleason, W. B.; Johnson, R. L. J. Pept. Res. 1997, 50, 1. (c) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1996, 61, 9437. (d) Chalmers, D. K.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 5927. (e) Genin, M. J.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1993, 36, 3481. (f) Hinds, M. G.; Welsh, J. H.; Brennand, D. M.; Fisher, J.; Glennie, M. J.; Richards, N. G. J.; Turner, D. L.; Robinson, J. A. J. Med. Chem. 1991, 34, 1777.
    • (1993) J. Med. Chem. , vol.36 , pp. 3481
    • Genin, M.J.1    Mishra, R.K.2    Johnson, R.L.3
  • 13
    • 0025848453 scopus 로고
    • Examples include: (a) Takeuchi, Y.; Marshall, G. R. J. Am. Chem. Soc. 1998, 120, 5363. (b) Baures, P. W.; Ojala, W. H.; Gleason, W. B.; Johnson, R. L. J. Pept. Res. 1997, 50, 1. (c) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1996, 61, 9437. (d) Chalmers, D. K.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 5927. (e) Genin, M. J.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1993, 36, 3481. (f) Hinds, M. G.; Welsh, J. H.; Brennand, D. M.; Fisher, J.; Glennie, M. J.; Richards, N. G. J.; Turner, D. L.; Robinson, J. A. J. Med. Chem. 1991, 34, 1777.
    • (1991) J. Med. Chem. , vol.34 , pp. 1777
    • Hinds, M.G.1    Welsh, J.H.2    Brennand, D.M.3    Fisher, J.4    Glennie, M.J.5    Richards, N.G.J.6    Turner, D.L.7    Robinson, J.A.8
  • 15
    • 0026551660 scopus 로고
    • Reviewed in ref 4. (a) Werner, M. H.; Wemmer, D. E. Biochemistry 1992, 31, 999. (b) Kim, E. E.; Varadarajan, R.; Wyckoff, H. W.; Richards, F. M. Biochemistry 1992, 31, 12304. (c) Epp, O.; Lattman, E. E.; Schiffer, M.; Huber, R.; Palm, W. Biochemistry 1975, 14, 4943.
    • (1992) Biochemistry , vol.31 , pp. 999
    • Werner, M.H.1    Wemmer, D.E.2
  • 16
    • 0026999215 scopus 로고
    • Reviewed in ref 4. (a) Werner, M. H.; Wemmer, D. E. Biochemistry 1992, 31, 999. (b) Kim, E. E.; Varadarajan, R.; Wyckoff, H. W.; Richards, F. M. Biochemistry 1992, 31, 12304. (c) Epp, O.; Lattman, E. E.; Schiffer, M.; Huber, R.; Palm, W. Biochemistry 1975, 14, 4943.
    • (1992) Biochemistry , vol.31 , pp. 12304
    • Kim, E.E.1    Varadarajan, R.2    Wyckoff, H.W.3    Richards, F.M.4
  • 17
    • 0016804680 scopus 로고
    • Reviewed in ref 4. (a) Werner, M. H.; Wemmer, D. E. Biochemistry 1992, 31, 999. (b) Kim, E. E.; Varadarajan, R.; Wyckoff, H. W.; Richards, F. M. Biochemistry 1992, 31, 12304. (c) Epp, O.; Lattman, E. E.; Schiffer, M.; Huber, R.; Palm, W. Biochemistry 1975, 14, 4943.
    • (1975) Biochemistry , vol.14 , pp. 4943
    • Epp, O.1    Lattman, E.E.2    Schiffer, M.3    Huber, R.4    Palm, W.5
  • 18
    • 0029073882 scopus 로고
    • Recent examples include the following: (a) segetalin A, Morita, H.; Yun, Y. S.; Takeya, K.; Itokawa, H.; Shiro, M. Tetrahedron 1995, 51, 5987. (b) cycloleonurinin, Morita, H.; Gonda, A.; Takeya, K.; Itokawa, H.; Hirano, T.; Oka, K.; Shirota, O. Tetrahedron 1997, 53, 7469. (c) aureobasidin E, Fujikawa, A.; In, Y.; Inoue, M.; Ishida, T.; Nemoto, N.; Kobayashi, Y.; Kataoka, R.; Ikai, K.; Takesako, K.; Kato, I. J. Org. Chem. 1994, 59, 570. (d) evolidine, Eggleston, D. S.; Baures, P. W.; Peishoff, C. E.; Kopple, K. D. J. Am. Chem. Soc. 1991, 113, 4410. (e) phakellistatin, Pettit, G. R.; Xu, J.-P.; Cichacz, Z. A.; Williams, M. D.; Dorsaz, A.-C.; Brune, D. C.; Boyd, M. R.; Cerny, R. L. Bioorg. Med. Chem. Lett. 1994, 4, 2091.
    • (1995) Tetrahedron , vol.51 , pp. 5987
    • Segetalin, A.1    Morita, H.2    Yun, Y.S.3    Takeya, K.4    Itokawa, H.5    Shiro, M.6
  • 19
    • 0030914853 scopus 로고    scopus 로고
    • Recent examples include the following: (a) segetalin A, Morita, H.; Yun, Y. S.; Takeya, K.; Itokawa, H.; Shiro, M. Tetrahedron 1995, 51, 5987. (b) cycloleonurinin, Morita, H.; Gonda, A.; Takeya, K.; Itokawa, H.; Hirano, T.; Oka, K.; Shirota, O. Tetrahedron 1997, 53, 7469. (c) aureobasidin E, Fujikawa, A.; In, Y.; Inoue, M.; Ishida, T.; Nemoto, N.; Kobayashi, Y.; Kataoka, R.; Ikai, K.; Takesako, K.; Kato, I. J. Org. Chem. 1994, 59, 570. (d) evolidine, Eggleston, D. S.; Baures, P. W.; Peishoff, C. E.; Kopple, K. D. J. Am. Chem. Soc. 1991, 113, 4410. (e) phakellistatin, Pettit, G. R.; Xu, J.-P.; Cichacz, Z. A.; Williams, M. D.; Dorsaz, A.-C.; Brune, D. C.; Boyd, M. R.; Cerny, R. L. Bioorg. Med. Chem. Lett. 1994, 4, 2091.
    • (1997) Tetrahedron , vol.53 , pp. 7469
    • Morita, H.1    Gonda, A.2    Takeya, K.3    Itokawa, H.4    Hirano, T.5    Oka, K.6    Shirota, O.7
  • 20
    • 0028329472 scopus 로고
    • Recent examples include the following: (a) segetalin A, Morita, H.; Yun, Y. S.; Takeya, K.; Itokawa, H.; Shiro, M. Tetrahedron 1995, 51, 5987. (b) cycloleonurinin, Morita, H.; Gonda, A.; Takeya, K.; Itokawa, H.; Hirano, T.; Oka, K.; Shirota, O. Tetrahedron 1997, 53, 7469. (c) aureobasidin E, Fujikawa, A.; In, Y.; Inoue, M.; Ishida, T.; Nemoto, N.; Kobayashi, Y.; Kataoka, R.; Ikai, K.; Takesako, K.; Kato, I. J. Org. Chem. 1994, 59, 570. (d) evolidine, Eggleston, D. S.; Baures, P. W.; Peishoff, C. E.; Kopple, K. D. J. Am. Chem. Soc. 1991, 113, 4410. (e) phakellistatin, Pettit, G. R.; Xu, J.-P.; Cichacz, Z. A.; Williams, M. D.; Dorsaz, A.-C.; Brune, D. C.; Boyd, M. R.; Cerny, R. L. Bioorg. Med. Chem. Lett. 1994, 4, 2091.
    • (1994) J. Org. Chem. , vol.59 , pp. 570
    • Fujikawa A, E.1    In, Y.2    Inoue, M.3    Ishida, T.4    Nemoto, N.5    Kobayashi, Y.6    Kataoka, R.7    Ikai, K.8    Takesako, K.9    Kato, I.10
  • 21
    • 0001199619 scopus 로고
    • Recent examples include the following: (a) segetalin A, Morita, H.; Yun, Y. S.; Takeya, K.; Itokawa, H.; Shiro, M. Tetrahedron 1995, 51, 5987. (b) cycloleonurinin, Morita, H.; Gonda, A.; Takeya, K.; Itokawa, H.; Hirano, T.; Oka, K.; Shirota, O. Tetrahedron 1997, 53, 7469. (c) aureobasidin E, Fujikawa, A.; In, Y.; Inoue, M.; Ishida, T.; Nemoto, N.; Kobayashi, Y.; Kataoka, R.; Ikai, K.; Takesako, K.; Kato, I. J. Org. Chem. 1994, 59, 570. (d) evolidine, Eggleston, D. S.; Baures, P. W.; Peishoff, C. E.; Kopple, K. D. J. Am. Chem. Soc. 1991, 113, 4410. (e) phakellistatin, Pettit, G. R.; Xu, J.-P.; Cichacz, Z. A.; Williams, M. D.; Dorsaz, A.-C.; Brune, D. C.; Boyd, M. R.; Cerny, R. L. Bioorg. Med. Chem. Lett. 1994, 4, 2091.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4410
    • Eggleston, D.S.1    Baures, P.W.2    Peishoff, C.E.3    Kopple, K.D.4
  • 22
    • 0028070344 scopus 로고
    • Recent examples include the following: (a) segetalin A, Morita, H.; Yun, Y. S.; Takeya, K.; Itokawa, H.; Shiro, M. Tetrahedron 1995, 51, 5987. (b) cycloleonurinin, Morita, H.; Gonda, A.; Takeya, K.; Itokawa, H.; Hirano, T.; Oka, K.; Shirota, O. Tetrahedron 1997, 53, 7469. (c) aureobasidin E, Fujikawa, A.; In, Y.; Inoue, M.; Ishida, T.; Nemoto, N.; Kobayashi, Y.; Kataoka, R.; Ikai, K.; Takesako, K.; Kato, I. J. Org. Chem. 1994, 59, 570. (d) evolidine, Eggleston, D. S.; Baures, P. W.; Peishoff, C. E.; Kopple, K. D. J. Am. Chem. Soc. 1991, 113, 4410. (e) phakellistatin, Pettit, G. R.; Xu, J.-P.; Cichacz, Z. A.; Williams, M. D.; Dorsaz, A.-C.; Brune, D. C.; Boyd, M. R.; Cerny, R. L. Bioorg. Med. Chem. Lett. 1994, 4, 2091.
    • (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 2091
    • Pettit, G.R.1    Xu, J.-P.2    Cichacz, Z.A.3    Williams, M.D.4    Dorsaz, A.-C.5    Brune, D.C.6    Boyd, M.R.7    Cerny, R.L.8
  • 23
    • 0028788636 scopus 로고
    • Recent examples include the following: (a) tuftsin, Valdeavella, C. V.; Blatt, H. D.; Pettitt, B. M. Int. J. Pept. Protein Res. 1995, 46, 372. (b) decorin/DS-PGII, Wang, Y.; Scott, P. G.; Sejbal, J.; Kotovych, G. Can. J. Chem. 1996, 74, 389.
    • (1995) Int. J. Pept. Protein Res. , vol.46 , pp. 372
    • Valdeavella, C.V.1    Blatt, H.D.2    Pettitt, B.M.3
  • 24
    • 0030110916 scopus 로고    scopus 로고
    • Recent examples include the following: (a) tuftsin, Valdeavella, C. V.; Blatt, H. D.; Pettitt, B. M. Int. J. Pept. Protein Res. 1995, 46, 372. (b) decorin/DS-PGII, Wang, Y.; Scott, P. G.; Sejbal, J.; Kotovych, G. Can. J. Chem. 1996, 74, 389.
    • (1996) Can. J. Chem. , vol.74 , pp. 389
    • Wang, Y.1    Scott, P.G.2    Sejbal, J.3    Kotovych, G.4
  • 33
    • 0028050923 scopus 로고
    • Reviewed in: (a) Fischer, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1415. (b) Liu, J.; Chen, C.-M.; Walsh, C. T. Biochemistry 1991, 30, 2306.
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 1415
    • Fischer, G.1
  • 34
    • 0025755354 scopus 로고
    • Reviewed in: (a) Fischer, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1415. (b) Liu, J.; Chen, C.-M.; Walsh, C. T. Biochemistry 1991, 30, 2306.
    • (1991) Biochemistry , vol.30 , pp. 2306
    • Liu, J.1    Chen, C.-M.2    Walsh, C.T.3
  • 69
    • 0000162407 scopus 로고
    • The use of carbon NMR spectroscopy to study twisted amide geometry is presented in: (a) Bennet, A. J.; Somayaji, V.; Brown, R. S.; Santarsiero, B. D. J. Am. Chem. Soc. 1991, 113, 7563. The relationship between bond length and twisted amide geometry is described in: (b) Shao, H.; Jiang, X.; Gantzel, P.; Goodman, M. Chem. Biol. 1994, 1, 231 and the characterization and reactivity of other distorted amides is discussed in refs 15-19 therein. (c) Bennet, A. J.; Wang, Q.-P.; Slebocka-Tilk, H.; Somayaji, V.; Brown, R. S. J. Am. Chem. Soc. 1990, 112, 6383. (d) Kirby, A. J.; Komarov, I. V.; Feeder, N. J. Am. Chem. Soc. 1998, 120, 7101.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7563
    • Bennet, A.J.1    Somayaji, V.2    Brown, R.S.3    Santarsiero, B.D.4
  • 70
    • 0028675648 scopus 로고
    • and the characterization and reactivity of other distorted amides is discussed in refs 15-19 therein
    • The use of carbon NMR spectroscopy to study twisted amide geometry is presented in: (a) Bennet, A. J.; Somayaji, V.; Brown, R. S.; Santarsiero, B. D. J. Am. Chem. Soc. 1991, 113, 7563. The relationship between bond length and twisted amide geometry is described in: (b) Shao, H.; Jiang, X.; Gantzel, P.; Goodman, M. Chem. Biol. 1994, 1, 231 and the characterization and reactivity of other distorted amides is discussed in refs 15-19 therein. (c) Bennet, A. J.; Wang, Q.-P.; Slebocka-Tilk, H.; Somayaji, V.; Brown, R. S. J. Am. Chem. Soc. 1990, 112, 6383. (d) Kirby, A. J.; Komarov, I. V.; Feeder, N. J. Am. Chem. Soc. 1998, 120, 7101.
    • (1994) Chem. Biol. , vol.1 , pp. 231
    • Shao, H.1    Jiang, X.2    Gantzel, P.3    Goodman, M.4
  • 71
    • 1542588044 scopus 로고
    • The use of carbon NMR spectroscopy to study twisted amide geometry is presented in: (a) Bennet, A. J.; Somayaji, V.; Brown, R. S.; Santarsiero, B. D. J. Am. Chem. Soc. 1991, 113, 7563. The relationship between bond length and twisted amide geometry is described in: (b) Shao, H.; Jiang, X.; Gantzel, P.; Goodman, M. Chem. Biol. 1994, 1, 231 and the characterization and reactivity of other distorted amides is discussed in refs 15-19 therein. (c) Bennet, A. J.; Wang, Q.-P.; Slebocka-Tilk, H.; Somayaji, V.; Brown, R. S. J. Am. Chem. Soc. 1990, 112, 6383. (d) Kirby, A. J.; Komarov, I. V.; Feeder, N. J. Am. Chem. Soc. 1998, 120, 7101.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6383
    • Bennet, A.J.1    Wang, Q.-P.2    Slebocka-Tilk, H.3    Somayaji, V.4    Brown, R.S.5
  • 72
    • 0032558075 scopus 로고    scopus 로고
    • The use of carbon NMR spectroscopy to study twisted amide geometry is presented in: (a) Bennet, A. J.; Somayaji, V.; Brown, R. S.; Santarsiero, B. D. J. Am. Chem. Soc. 1991, 113, 7563. The relationship between bond length and twisted amide geometry is described in: (b) Shao, H.; Jiang, X.; Gantzel, P.; Goodman, M. Chem. Biol. 1994, 1, 231 and the characterization and reactivity of other distorted amides is discussed in refs 15-19 therein. (c) Bennet, A. J.; Wang, Q.-P.; Slebocka-Tilk, H.; Somayaji, V.; Brown, R. S. J. Am. Chem. Soc. 1990, 112, 6383. (d) Kirby, A. J.; Komarov, I. V.; Feeder, N. J. Am. Chem. Soc. 1998, 120, 7101.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 7101
    • Kirby, A.J.1    Komarov, I.V.2    Feeder, N.3
  • 74
    • 0344997000 scopus 로고    scopus 로고
    • note
    • 2 = 0.1140 for all data; GOF = 0.986. The author has deposited the atomic coordinates for the structure of 1d with the Cambridge Crystallographic Data Center. The coordinates can be obtained, on request, from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ, U.K.
  • 87
    • 0030439691 scopus 로고    scopus 로고
    • For representative examples, see: (a) Benedetti, E.; Di Blasio, B.; Iacovino, R.; Menchise, V.; Saviano, M.; Pedone, C.; Bonora, G. M.; Ettorre, A.; Graci, L.; Formaggio, F.; Crisma, M.; Valle, G.; Toniolo, C. J. Chem. Soc., Perkin Trans. 2 1997, 2023. (b) Toniolo, C.; Crisma, M.; Formaggio, F.; Benedetti, E.; Santini, A.; Iacovino, R.; Saviano, M.; Di Blasio, B.; Pedone, C.; Kamphuis, J. Biopolymers 1996, 40, 519. (c) Prasad, S.; Rao, R. B.; Balaram, P. Biopolymers 1995, 35, 11.
    • (1996) Biopolymers , vol.40 , pp. 519
    • Toniolo, C.1    Crisma, M.2    Formaggio, F.3    Benedetti, E.4    Santini, A.5    Iacovino, R.6    Saviano, M.7    Di Blasio, B.8    Pedone, C.9    Kamphuis, J.10
  • 88
    • 0028835439 scopus 로고
    • For representative examples, see: (a) Benedetti, E.; Di Blasio, B.; Iacovino, R.; Menchise, V.; Saviano, M.; Pedone, C.; Bonora, G. M.; Ettorre, A.; Graci, L.; Formaggio, F.; Crisma, M.; Valle, G.; Toniolo, C. J. Chem. Soc., Perkin Trans. 2 1997, 2023. (b) Toniolo, C.; Crisma, M.; Formaggio, F.; Benedetti, E.; Santini, A.; Iacovino, R.; Saviano, M.; Di Blasio, B.; Pedone, C.; Kamphuis, J. Biopolymers 1996, 40, 519. (c) Prasad, S.; Rao, R. B.; Balaram, P. Biopolymers 1995, 35, 11.
    • (1995) Biopolymers , vol.35 , pp. 11
    • Prasad, S.1    Rao, R.B.2    Balaram, P.3
  • 97
    • 0020130477 scopus 로고
    • 5-Alkylproline examples include: (a) Delaney, N. G.; Madison, V. Int. J. Pept. Protein Res. 1982, 19, 543. (b) Magaard, V. W.; Sanchez, R. M.; Bean, J. W.; Moore, M. L. Tetrahedron Lett. 1993, 34, 381. (c) Overberger, C. G.; David, K.-H. Macromolecules 1972, 5, 373. (d) Overberger, C. G.; Han, M. J. J. Polym. Sci.: Polym. Chem. Ed. 1975, 13, 2251. (e) Overberger, C. G.; Han, M. J. Pure Appl. Chem. 1974, 39, 33. (f) Ahn, K.-D.; Overberger, C. G. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1699. (g) Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1741. (h) Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1751. (i) McGrady, K. A. W.; Overberger, C. G. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1987, 28, 429.
    • (1982) Int. J. Pept. Protein Res. , vol.19 , pp. 543
    • Delaney, N.G.1    Madison, V.2
  • 98
    • 0027395374 scopus 로고
    • 5-Alkylproline examples include: (a) Delaney, N. G.; Madison, V. Int. J. Pept. Protein Res. 1982, 19, 543. (b) Magaard, V. W.; Sanchez, R. M.; Bean, J. W.; Moore, M. L. Tetrahedron Lett. 1993, 34, 381. (c) Overberger, C. G.; David, K.-H. Macromolecules 1972, 5, 373. (d) Overberger, C. G.; Han, M. J. J. Polym. Sci.: Polym. Chem. Ed. 1975, 13, 2251. (e) Overberger, C. G.; Han, M. J. Pure Appl. Chem. 1974, 39, 33. (f) Ahn, K.-D.; Overberger, C. G. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1699. (g) Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1741. (h) Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1751. (i) McGrady, K. A. W.; Overberger, C. G. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1987, 28, 429.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 381
    • Magaard, V.W.1    Sanchez, R.M.2    Bean, J.W.3    Moore, M.L.4
  • 99
    • 0000991909 scopus 로고
    • 5-Alkylproline examples include: (a) Delaney, N. G.; Madison, V. Int. J. Pept. Protein Res. 1982, 19, 543. (b) Magaard, V. W.; Sanchez, R. M.; Bean, J. W.; Moore, M. L. Tetrahedron Lett. 1993, 34, 381. (c) Overberger, C. G.; David, K.-H. Macromolecules 1972, 5, 373. (d) Overberger, C. G.; Han, M. J. J. Polym. Sci.: Polym. Chem. Ed. 1975, 13, 2251. (e) Overberger, C. G.; Han, M. J. Pure Appl. Chem. 1974, 39, 33. (f) Ahn, K.-D.; Overberger, C. G. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1699. (g) Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1741. (h) Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1751. (i) McGrady, K. A. W.; Overberger, C. G. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1987, 28, 429.
    • (1972) Macromolecules , vol.5 , pp. 373
    • Overberger, C.G.1    David, K.-H.2
  • 100
    • 0016564958 scopus 로고
    • 5-Alkylproline examples include: (a) Delaney, N. G.; Madison, V. Int. J. Pept. Protein Res. 1982, 19, 543. (b) Magaard, V. W.; Sanchez, R. M.; Bean, J. W.; Moore, M. L. Tetrahedron Lett. 1993, 34, 381. (c) Overberger, C. G.; David, K.-H. Macromolecules 1972, 5, 373. (d) Overberger, C. G.; Han, M. J. J. Polym. Sci.: Polym. Chem. Ed. 1975, 13, 2251. (e) Overberger, C. G.; Han, M. J. Pure Appl. Chem. 1974, 39, 33. (f) Ahn, K.-D.; Overberger, C. G. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1699. (g) Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1741. (h) Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1751. (i) McGrady, K. A. W.; Overberger, C. G. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1987, 28, 429.
    • (1975) J. Polym. Sci.: Polym. Chem. Ed. , vol.13 , pp. 2251
    • Overberger, C.G.1    Han, M.J.2
  • 101
    • 0008878864 scopus 로고
    • 5-Alkylproline examples include: (a) Delaney, N. G.; Madison, V. Int. J. Pept. Protein Res. 1982, 19, 543. (b) Magaard, V. W.; Sanchez, R. M.; Bean, J. W.; Moore, M. L. Tetrahedron Lett. 1993, 34, 381. (c) Overberger, C. G.; David, K.-H. Macromolecules 1972, 5, 373. (d) Overberger, C. G.; Han, M. J. J. Polym. Sci.: Polym. Chem. Ed. 1975, 13, 2251. (e) Overberger, C. G.; Han, M. J. Pure Appl. Chem. 1974, 39, 33. (f) Ahn, K.-D.; Overberger, C. G. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1699. (g) Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1741. (h) Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1751. (i) McGrady, K. A. W.; Overberger, C. G. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1987, 28, 429.
    • (1974) Pure Appl. Chem. , vol.39 , pp. 33
    • Overberger, C.G.1    Han, M.J.2
  • 102
    • 0020765201 scopus 로고
    • 5-Alkylproline examples include: (a) Delaney, N. G.; Madison, V. Int. J. Pept. Protein Res. 1982, 19, 543. (b) Magaard, V. W.; Sanchez, R. M.; Bean, J. W.; Moore, M. L. Tetrahedron Lett. 1993, 34, 381. (c) Overberger, C. G.; David, K.-H. Macromolecules 1972, 5, 373. (d) Overberger, C. G.; Han, M. J. J. Polym. Sci.: Polym. Chem. Ed. 1975, 13, 2251. (e) Overberger, C. G.; Han, M. J. Pure Appl. Chem. 1974, 39, 33. (f) Ahn, K.-D.; Overberger, C. G. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1699. (g) Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1741. (h) Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1751. (i) McGrady, K. A. W.; Overberger, C. G. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1987, 28, 429.
    • (1983) J. Polym. Sci.: Polym. Chem. Ed. , vol.21 , pp. 1699
    • Ahn, K.-D.1    Overberger, C.G.2
  • 103
    • 0020765276 scopus 로고
    • 5-Alkylproline examples include: (a) Delaney, N. G.; Madison, V. Int. J. Pept. Protein Res. 1982, 19, 543. (b) Magaard, V. W.; Sanchez, R. M.; Bean, J. W.; Moore, M. L. Tetrahedron Lett. 1993, 34, 381. (c) Overberger, C. G.; David, K.-H. Macromolecules 1972, 5, 373. (d) Overberger, C. G.; Han, M. J. J. Polym. Sci.: Polym. Chem. Ed. 1975, 13, 2251. (e) Overberger, C. G.; Han, M. J. Pure Appl. Chem. 1974, 39, 33. (f) Ahn, K.-D.; Overberger, C. G. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1699. (g) Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1741. (h) Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1751. (i) McGrady, K. A. W.; Overberger, C. G. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1987, 28, 429.
    • (1983) J. Polym. Sci.: Polym. Chem. Ed. , vol.21 , pp. 1741
    • Yang, W.W.-Y.1    Overberger, C.G.2    Venkatachalam, C.M.3
  • 104
    • 0020766390 scopus 로고
    • 5-Alkylproline examples include: (a) Delaney, N. G.; Madison, V. Int. J. Pept. Protein Res. 1982, 19, 543. (b) Magaard, V. W.; Sanchez, R. M.; Bean, J. W.; Moore, M. L. Tetrahedron Lett. 1993, 34, 381. (c) Overberger, C. G.; David, K.-H. Macromolecules 1972, 5, 373. (d) Overberger, C. G.; Han, M. J. J. Polym. Sci.: Polym. Chem. Ed. 1975, 13, 2251. (e) Overberger, C. G.; Han, M. J. Pure Appl. Chem. 1974, 39, 33. (f) Ahn, K.-D.; Overberger, C. G. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1699. (g) Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1741. (h) Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1751. (i) McGrady, K. A. W.; Overberger, C. G. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1987, 28, 429.
    • (1983) J. Polym. Sci.: Polym. Chem. Ed. , vol.21 , pp. 1751
    • Yang, W.W.-Y.1    Overberger, C.G.2    Venkatachalam, C.M.3
  • 105
    • 0345428111 scopus 로고
    • 5-Alkylproline examples include: (a) Delaney, N. G.; Madison, V. Int. J. Pept. Protein Res. 1982, 19, 543. (b) Magaard, V. W.; Sanchez, R. M.; Bean, J. W.; Moore, M. L. Tetrahedron Lett. 1993, 34, 381. (c) Overberger, C. G.; David, K.-H. Macromolecules 1972, 5, 373. (d) Overberger, C. G.; Han, M. J. J. Polym. Sci.: Polym. Chem. Ed. 1975, 13, 2251. (e) Overberger, C. G.; Han, M. J. Pure Appl. Chem. 1974, 39, 33. (f) Ahn, K.-D.; Overberger, C. G. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1699. (g) Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1741. (h) Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1751. (i) McGrady, K. A. W.; Overberger, C. G. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1987, 28, 429.
    • (1987) Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) , vol.28 , pp. 429
    • McGrady, K.A.W.1    Overberger, C.G.2
  • 106
    • 0028010191 scopus 로고
    • 5-Alkyl-4-thiaproline analogues: (a) Nefzi, A.; Schenk, K.; Mutter, M. Protein Pept. Lett. 1994, 1, 66. (b) Savrda, J. In Peptides 1976; Loffet, A., Ed.; Edition de l'Université de Bruxelles: Brussels, 1976; p 653. 5-Alkyl-4-thia- and 4-oxaproline analogues: (c) Keller, M.; Sager, C.; Dumy, P.; Schutkowski, M.; Fischer, G. S.; Mutter, M. J. Am. Chem. Soc. 1998, 120, 2714. (d) Dumy, P.; Keller, M.; Ryan, D. E.; Rohwedder, B.; Wöhr, T.; Mutter, M. J. Am. Chem. Soc. 1997, 119, 918.
    • (1994) Protein Pept. Lett. , vol.1 , pp. 66
    • Nefzi, A.1    Schenk, K.2    Mutter, M.3
  • 107
    • 0028010191 scopus 로고
    • Loffet, A., Ed.; Edition de l'Université de Bruxelles: Brussels
    • 5-Alkyl-4-thiaproline analogues: (a) Nefzi, A.; Schenk, K.; Mutter, M. Protein Pept. Lett. 1994, 1, 66. (b) Savrda, J. In Peptides 1976; Loffet, A., Ed.; Edition de l'Université de Bruxelles: Brussels, 1976; p 653. 5-Alkyl-4-thia- and 4-oxaproline analogues: (c) Keller, M.; Sager, C.; Dumy, P.; Schutkowski, M.; Fischer, G. S.; Mutter, M. J. Am. Chem. Soc. 1998, 120, 2714. (d) Dumy, P.; Keller, M.; Ryan, D. E.; Rohwedder, B.; Wöhr, T.; Mutter, M. J. Am. Chem. Soc. 1997, 119, 918.
    • (1976) Peptides 1976 , pp. 653
    • Savrda, J.1
  • 108
    • 0032054074 scopus 로고    scopus 로고
    • 5-Alkyl-4-thiaproline analogues: (a) Nefzi, A.; Schenk, K.; Mutter, M. Protein Pept. Lett. 1994, 1, 66. (b) Savrda, J. In Peptides 1976; Loffet, A., Ed.; Edition de l'Université de Bruxelles: Brussels, 1976; p 653. 5-Alkyl-4-thia- and 4-oxaproline analogues: (c) Keller, M.; Sager, C.; Dumy, P.; Schutkowski, M.; Fischer, G. S.; Mutter, M. J. Am. Chem. Soc. 1998, 120, 2714. (d) Dumy, P.; Keller, M.; Ryan, D. E.; Rohwedder, B.; Wöhr, T.; Mutter, M. J. Am. Chem. Soc. 1997, 119, 918.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 2714
    • Keller, M.1    Sager, C.2    Dumy, P.3    Schutkowski, M.4    Fischer, G.S.5    Mutter, M.6
  • 109
    • 0031028387 scopus 로고    scopus 로고
    • 5-Alkyl-4-thiaproline analogues: (a) Nefzi, A.; Schenk, K.; Mutter, M. Protein Pept. Lett. 1994, 1, 66. (b) Savrda, J. In Peptides 1976; Loffet, A., Ed.; Edition de l'Université de Bruxelles: Brussels, 1976; p 653. 5-Alkyl-4-thia- and 4-oxaproline analogues: (c) Keller, M.; Sager, C.; Dumy, P.; Schutkowski, M.; Fischer, G. S.; Mutter, M. J. Am. Chem. Soc. 1998, 120, 2714. (d) Dumy, P.; Keller, M.; Ryan, D. E.; Rohwedder, B.; Wöhr, T.; Mutter, M. J. Am. Chem. Soc. 1997, 119, 918.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 918
    • Dumy, P.1    Keller, M.2    Ryan, D.E.3    Rohwedder, B.4    Wöhr, T.5    Mutter, M.6


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