Chemo-enzymic synthesis of protected cyano derivatives of glutamate

Tetrahedron Letters

Volumn 39, Issue 32, 1998, Pages 5775-5778

  Dugave, Christophe ^a,b   Cluzeau, Jérôme ^a   Ménez, André ^a   Gaudry, Michel ^b   Marquet, Andrée ^b  

^a CEA SACLAY   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

GLUTAMIC ACID DERIVATIVE; NITRILE;

ARTICLE; CATALYSIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032490967     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01207-6     Document Type: Article

References (15)

1. 1-Dugave, C.; Ménez, A.; J. Org. Chem. 1996, 61, 6067-6070.
2. 2-Dugave, C.; Ménez, A.; Recent Research Developments in Organic Chemistry 1997, 1, 299-312, Pandalay, S. G. Ed., Trivandrum, India.
3. 3-Dugave, C.; Ménez, A.; Tetrahedron: Asymm. 1997, 8, 1453-1465.
4. 4-Rosowsky, A.; Bader, H.; Freisheim, J. H.; J. Med. Chem. 1991, 34, 203-208. For the stereoselective hydrolysis of Z-γ-carboxyglutamate triester using papain, see: Clapès, P.; Valverde, I.; Jaime, C.; J. L. Torres; Tetrahedron Lett. 1996, 37, 417-418.
5. 4-Rosowsky, A.; Bader, H.; Freisheim, J. H.; J. Med. Chem. 1991, 34, 203-208. For the stereoselective hydrolysis of Z-γ-carboxyglutamate triester using papain, see: Clapès, P.; Valverde, I.; Jaime, C.; J. L. Torres; Tetrahedron Lett. 1996, 37, 417-418.
6. 5-Bory, S.; Gaudry, M.; Marquet, A.; Azerad, R.; Biochem. Biophys. Res. Commun. 1979, 87, 85-91.
7. 6-The Michael addition did not take place without HMPA (10 to 20%) as a cosolvent.
8. 7-Tong, J. H.; Petitclerc, C.; D'Iorio, A.; Benoiton, N. L.; Can. J. Biochem. 1971, 242, 173-181.
9. 4: C, 53.92; H, 6.41; N, 15.72; found: C, 53.65; H, 6.49; N, 15.76.
10. 2O C, 48.70; H, 6.32; N, 15.49; found: C, 48.94; H, 6.34; N, 14.99.
11. 10-Einarsson, S.; Josephsson, B.; Möler, P.; Sanchez, D.; Anal. Chem. 1987, 59, 1191-1195.
12. 1/2 = 90 min at pH 7.4, 30 min at pH 5.4 and 10 min at pH 4.7), confirmed the expected lack of configurational stability of the γ-carbon and precluded a separation of the diastereomers.
13. 12 In the same way, cyanoglutamic diester 3 was not saponified in the buffer and required more drastic conditions (1 equivalent LiOH in acetonitrile:water 3:1) for selective deprotection of the cyanoacetic moiety.
14. 13-Petkov, D.; Christova, E.; Stoineva, I.; Biochem. Biophys. Acta 1978, 527, 131-141.
15. 14-Petkov, D.; Stoineva, I.; Bioorg. Chem. 1980, 9, 318-324.