Regioselective enolization and alkylation of 4-oxo-N-(9-phenylfluoren-9-yl)proline: Synthesis of enantiopure proline-valine and hydroxyproline-valine chimeras

Journal of Organic Chemistry

Volumn 61, Issue 1, 1996, Pages 202-209

  Sharma, Raman ^a   Lubell, William D ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; CHIMERIC PROTEIN; DIPEPTIDE; UNCLASSIFIED DRUG; VALINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030030384     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9514984     Document Type: Article

References (71)

1. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
2. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
3. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
4. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
5. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
6. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
7. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
8. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
9. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
10. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
11. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
12. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
13. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
14. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
15. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
16. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
17. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
18. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
19. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
20. Syntheses and uses of 3-carboxyproline, a proline-aspartate chimera, are described in (a) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Godfrey, C. R. A. Tetrahedron 1995, 51, 5169. (b) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron Lett. 1994, 35, 8859. (c) Humphrey, J. M ; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467. (d) Hashimoto, K.; Yamamoto, O.; Horikawa, M.; Ohfune, Y.; Shirahama, H. Bioorg. Med. Chem. Lett. 1994, 4, 1851. (e) Sasaki, N. A.; Pauly, R.; Fontaine, C.; Chiaroni, A.; Riche, C.; Potier, P. Tetrahedron Lett. 1994, 35, 241. Syntheses and uses of proline-glutamate chimeras,4-carboxyproline, and trans-2-carboxy-3-pyrrolidineacetic acid are described in the following: (f) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. J. Med. Chem. 1991, 34, 717. (g) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J Chem. Soc., Perkin Trans. 1 1992, 2615. (h) Tsai, C.; Schneider, J. A.; Lehmann, J. Neurosci. Lett. 1988, 92, 298. (i) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057. (j) Yoo, S.-E.; Lee, S.-H.; Kim, N.-J. Tetrahedron Lett. 1988, 29, 2195. (k) Sato, T.; Matsubayashi, K.-I.; Yamamoto, K.; Ishikawa, H.; Ishibashi, H.; Ikeda, M. Heterocycles 1995, 40, 261. Synthesis of 4-(carboxymethyl)proline, a proline-α-aminoadipic acid chimera, is presented in: (l) Pellicciari, R.; Arenare, L.; De Caprariis, P.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251. Synthesis of 4-(guanidinomethyl)proline, a proline-arginine chimera, is presented in: (m) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. Syntheses of 3-phenylproline, a proline-phenylalanine chimera, are presented in: (n) Chung, J Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270. (o) Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351 (p) Belokon', Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075. (q) Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710. Syntheses of 3-methylproline, a proline-valine chimera, are reported in ref 25 as well as: (r) Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875. (s) Mauger, A. B. J. Org. Chem. 1981, 46, 1032. (t) Esch, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659. Syntheses of proline-norleucine and proline-methionine chimeras are respectively presented in refs 2a and 2c.
21. (a) Holladay, M. W.; Lin, C. W.; May, C. S.; Garvey, D. S.; Witte, D. G.; Miller, T. R.; Wolfram, C. A. W.; Nadzan, A. M. J. Med. Chem. 1991, 34, 457.
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31. The use of β-alkylprolines in collagenase inhibitors is reported in: (a) Ghose, A. K.; Logan, M. E.; Treasurywala, A. M.; Wang, H.; Wahl, R. C.; Tomczuk, B. E.; Gowravaram, M. R.; Jaeger, E. P.; Wendoloski, J. J. J. Am. Chem. Soc. 1995, 117, 4671. The use of β-alkylprolines in collagen proline hydroxylase inhibitors is reported in: (b) Hutton, J. J., Jr.; Marglin, A.; Witkop, B.; Kurtz, J.; Berger, A.; Udenfriend, S. Arch. Biochem. Biophys. 1968, 125, 779.
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61. 13C NMR δ 55.5, 66, 67, 71.6, 77.1, 92 1, 158.1, 174.4.
62. The structure of (4R)-9 was solved at l'Université de Montréal X-ray facility using direct methods (SHELXS 86). The author has deposited the atomic coordinates for the structure of (4R)-9 with the Cambridge Crystallographic Data Center. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
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70. + 142 (100).
71. Knorr, R.; Trzeciak, A.; Bannwarth, W.; Gillessen, D Tetrahedron Lett. 1989, 30, 1927.