Asymmetric synthesis of L-proline regio- and stereoselectively labelled with deuterium

Tetrahedron Asymmetry

Volumn 10, Issue 5, 1999, Pages 937-945

  Oba, Makoto ^a   Terauchi, Tsutomu ^a   Miyakawa, Akiko ^a   Nishiyama, Kozaburo ^a  

^a TOKAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; DEUTERIUM; METAL; METHYL GROUP; PROLINE DERIVATIVE; PYROGLUTAMIC ACID DERIVATIVE; RUTHENIUM DERIVATIVE;

ARTICLE; CATALYSIS; CONFORMATION; ISOMER; ISOTOPE LABELING; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033548391     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00083-X     Document Type: Article

References (35)

1. Young, D. W. Stereochemistry of Metabolic Reactions of Amino Acids. In Topics In Stereochemistry; Eliel, E. L.; Wilen, S. H., Eds.; John Wiley: New York, 1994; Vol. 21, pp. 381-465.
2. Wuthrich, K. NMR of Proteins and Nucleic Acids; John Wiley & Sons: New York, 1986; Roberts, G. C. K. NMR of Macromolecules. A Practical Approach; Oxford University Press: Oxford, 1993.
3. Wuthrich, K. NMR of Proteins and Nucleic Acids; John Wiley & Sons: New York, 1986; Roberts, G. C. K. NMR of Macromolecules. A Practical Approach; Oxford University Press: Oxford, 1993.
4. Nishiyama, K.; Oba, M.; Ueno, R.; Morita, A.; Nakamura, Y.; Kainosho, M. J. Labelled Compds. Radiopharm. 1994, 34, 831-837; Oba, M.; Ueno, R.; Fukuoka, M.; Kainosho, M.; Nishiyama, K. J. Chem. Soc., Perkin Trans. 1 1995, 1603-1609; Oba, M.; Nakajima, S.; Nishiyama, K. J. Chem. Soc., Chem. Commun. 1996, 1875-1876; Oba, M.; Terauchi, T.; Miyakawa, A.; Kamo, H.; Nishiyama, K. Tetrahedron Lett. 1998, 39, 1595-1598; Oba, M.; Terauchi, T.; Owari, Y.; Imai, Y.; Motoyama, I.; Nishiyama, K. J. Chem. Soc., Perkin Trans. 1 1998, 1275-1281.
5. Nishiyama, K.; Oba, M.; Ueno, R.; Morita, A.; Nakamura, Y.; Kainosho, M. J. Labelled Compds. Radiopharm. 1994, 34, 831-837; Oba, M.; Ueno, R.; Fukuoka, M.; Kainosho, M.; Nishiyama, K. J. Chem. Soc., Perkin Trans. 1 1995, 1603-1609; Oba, M.; Nakajima, S.; Nishiyama, K. J. Chem. Soc., Chem. Commun. 1996, 1875-1876; Oba, M.; Terauchi, T.; Miyakawa, A.; Kamo, H.; Nishiyama, K. Tetrahedron Lett. 1998, 39, 1595-1598; Oba, M.; Terauchi, T.; Owari, Y.; Imai, Y.; Motoyama, I.; Nishiyama, K. J. Chem. Soc., Perkin Trans. 1 1998, 1275-1281.
6. Nishiyama, K.; Oba, M.; Ueno, R.; Morita, A.; Nakamura, Y.; Kainosho, M. J. Labelled Compds. Radiopharm. 1994, 34, 831-837; Oba, M.; Ueno, R.; Fukuoka, M.; Kainosho, M.; Nishiyama, K. J. Chem. Soc., Perkin Trans. 1 1995, 1603-1609; Oba, M.; Nakajima, S.; Nishiyama, K. J. Chem. Soc., Chem. Commun. 1996, 1875-1876; Oba, M.; Terauchi, T.; Miyakawa, A.; Kamo, H.; Nishiyama, K. Tetrahedron Lett. 1998, 39, 1595-1598; Oba, M.; Terauchi, T.; Owari, Y.; Imai, Y.; Motoyama, I.; Nishiyama, K. J. Chem. Soc., Perkin Trans. 1 1998, 1275-1281.
7. Nishiyama, K.; Oba, M.; Ueno, R.; Morita, A.; Nakamura, Y.; Kainosho, M. J. Labelled Compds. Radiopharm. 1994, 34, 831-837; Oba, M.; Ueno, R.; Fukuoka, M.; Kainosho, M.; Nishiyama, K. J. Chem. Soc., Perkin Trans. 1 1995, 1603-1609; Oba, M.; Nakajima, S.; Nishiyama, K. J. Chem. Soc., Chem. Commun. 1996, 1875-1876; Oba, M.; Terauchi, T.; Miyakawa, A.; Kamo, H.; Nishiyama, K. Tetrahedron Lett. 1998, 39, 1595-1598; Oba, M.; Terauchi, T.; Owari, Y.; Imai, Y.; Motoyama, I.; Nishiyama, K. J. Chem. Soc., Perkin Trans. 1 1998, 1275-1281.
8. Nishiyama, K.; Oba, M.; Ueno, R.; Morita, A.; Nakamura, Y.; Kainosho, M. J. Labelled Compds. Radiopharm. 1994, 34, 831-837; Oba, M.; Ueno, R.; Fukuoka, M.; Kainosho, M.; Nishiyama, K. J. Chem. Soc., Perkin Trans. 1 1995, 1603-1609; Oba, M.; Nakajima, S.; Nishiyama, K. J. Chem. Soc., Chem. Commun. 1996, 1875-1876; Oba, M.; Terauchi, T.; Miyakawa, A.; Kamo, H.; Nishiyama, K. Tetrahedron Lett. 1998, 39, 1595-1598; Oba, M.; Terauchi, T.; Owari, Y.; Imai, Y.; Motoyama, I.; Nishiyama, K. J. Chem. Soc., Perkin Trans. 1 1998, 1275-1281.
9. Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv. Protein Chem. 1985, 37, 1-109; Degrado, W. F. Adv. Protein Chem. 1988, 39, 51-118.
10. Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv. Protein Chem. 1985, 37, 1-109; Degrado, W. F. Adv. Protein Chem. 1988, 39, 51-118.
11. Hirschmann, R. Angew. Chem., Int. Ed. Engl. 1991, 30, 1278-1301; Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-1267.
12. Hirschmann, R. Angew. Chem., Int. Ed. Engl. 1991, 30, 1278-1301; Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-1267.
13. Fujita, Y.; Gottlieb, A.; Peterkogsky, B.; Udenfriend, S.; Witkop, B. J. Am. Chem. Soc. 1964, 86, 4709-4716.
14. Baldwin, J. E.; Field, R. A.; Lawrence, C. C.; Merritt, K. D.; Schofield, C. J. Tetrahedron Lett. 1993, 34, 7489-7492.
15. Robertson, A. V.; Witkop, B. J. Am. Chem. Soc. 1960, 82, 5008-5009; Prockop, D. J.; Ebert, P. S.; Shapiro, B. M. Arch. Biochem. Biophys. 1962, 8, 305-309; Ebert, P. S.; Prockop, D. J. Biochem. Biophys. Res. Commun. 1962, 8, 305-309.
16. Robertson, A. V.; Witkop, B. J. Am. Chem. Soc. 1960, 82, 5008-5009; Prockop, D. J.; Ebert, P. S.; Shapiro, B. M. Arch. Biochem. Biophys. 1962, 8, 305-309; Ebert, P. S.; Prockop, D. J. Biochem. Biophys. Res. Commun. 1962, 8, 305-309.
17. Robertson, A. V.; Witkop, B. J. Am. Chem. Soc. 1960, 82, 5008-5009; Prockop, D. J.; Ebert, P. S.; Shapiro, B. M. Arch. Biochem. Biophys. 1962, 8, 305-309; Ebert, P. S.; Prockop, D. J. Biochem. Biophys. Res. Commun. 1962, 8, 305-309.
18. Dieterich, P.; Young, D. W. Tetrahedron Lett. 1993, 34, 5455-5458.
19. Gramatica, P.; Manitto, P.; Manzocchi, A.; Santaniello, E. J. Labelled Compd. Radiopharm. 1981, 18, 955-962.
20. Oba, M.; Terauchi, T.; Hashimoto, J.; Tanaka, T.; Nishiyama, K. Tetrahedron Lett. 1997, 38, 5515-5518.
21. Rueger, H.; Benn, M. H. Can. J. Chem. 1982, 60, 2918-2920; Doromoy, J.-R. Synthesis 1982, 753-756; Doromoy, J.-R. Angew. Chem., Int. Ed. Engl. 1980, 19, 742-743.
22. Rueger, H.; Benn, M. H. Can. J. Chem. 1982, 60, 2918-2920; Doromoy, J.-R. Synthesis 1982, 753-756; Doromoy, J.-R. Angew. Chem., Int. Ed. Engl. 1980, 19, 742-743.
23. Rueger, H.; Benn, M. H. Can. J. Chem. 1982, 60, 2918-2920; Doromoy, J.-R. Synthesis 1982, 753-756; Doromoy, J.-R. Angew. Chem., Int. Ed. Engl. 1980, 19, 742-743.
24. Anteunis, M. J. O.; Borremans, F. A. M.; Becu, C.; Sleeckx, J. Int. J. Peptide Protein Res. 1979, 14, 445-450.
25. Hondrelis, J.; Lonergan, G.; Voliotis, S.; Matsoukas, J. Tetrahedron 1990, 46, 565-576.
26. Montiere, H. J. Synthesis 1974, 137; Ohfune, Y.; Tomita, M. J. Am. Chem. Soc. 1982, 104, 3511-3513; Langlois, N.; Rojas, A. Tetrahedron Lett. 1993, 34, 2477-2480.
27. Montiere, H. J. Synthesis 1974, 137; Ohfune, Y.; Tomita, M. J. Am. Chem. Soc. 1982, 104, 3511-3513; Langlois, N.; Rojas, A. Tetrahedron Lett. 1993, 34, 2477-2480.
28. Montiere, H. J. Synthesis 1974, 137; Ohfune, Y.; Tomita, M. J. Am. Chem. Soc. 1982, 104, 3511-3513; Langlois, N.; Rojas, A. Tetrahedron Lett. 1993, 34, 2477-2480.
29. Pedregal, C.; Ezquerra, J.; Escribano, A.; Carreno, M. C.; Garcia Ruano, J. L. Tetrahedron Lett. 1994, 35, 2053-2056.
30. Thaning, M.; Winstrand, L.-G. J. Org. Chem. 1990, 55, 1406-1408; Bernardi, A.; Micheli, F.; Potenza, D.; Scolastico, C.; Villa, R. Tetrahedron Lett. 1990, 31, 4949-4952; Ryu, Y.; Kim, G. J. Org. Chem. 1995, 60, 103-108.
31. Thaning, M.; Winstrand, L.-G. J. Org. Chem. 1990, 55, 1406-1408; Bernardi, A.; Micheli, F.; Potenza, D.; Scolastico, C.; Villa, R. Tetrahedron Lett. 1990, 31, 4949-4952; Ryu, Y.; Kim, G. J. Org. Chem. 1995, 60, 103-108.
32. Thaning, M.; Winstrand, L.-G. J. Org. Chem. 1990, 55, 1406-1408; Bernardi, A.; Micheli, F.; Potenza, D.; Scolastico, C.; Villa, R. Tetrahedron Lett. 1990, 31, 4949-4952; Ryu, Y.; Kim, G. J. Org. Chem. 1995, 60, 103-108.
33. Jeroncic, L. O.; Cabal, M. P.; Danishefsky, S. J.; Shulte, G. M. J. Org. Chem. 1991, 56, 387-395.
34. Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540-4552.
35. Yoshifuji, S.; Tanaka, K.; Kawai, T.; Nitta, Y Chem. Pharm. Bull. 1986, 34, 3873-3878.