Synthesis of 2-substituted 4methyleneglutamic acids and their cyclopropyl analogues

Anales de Quimica

Volumn 92, Issue 6, 1996, Pages 362-369

  Guillena, Gabriela ^a   Micö, Irene ^a   Nâjera, Carmen ^b   Ezquerra, Jesus ^b   Pedregal, Concepciön ^c   Ezquerra, J ^c   Pedregal, C ^a,b,c  

^a UNIVERSITY OF ALICANTE   (Spain)

^b ELI LILLY AND COMPANY   (Spain)

^c A alkylglutamic Acids ^*

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000288010     PISSN: 11302283     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (18)

1. This compound 1 is a natural amino acid isolated from several plants [2|, and in peptides inhibits the vitamin K mediated y-carboxylation of glutamic acid, which is important in the blood clotting process [3]
2. 2a Done J. Fovvden L ( 1952) Biochem J 51:451 -458
3. b Fowden L ( 1964) Ann Rev Biochem 33: 173-204
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5. Shevvry PR. Fovvden L (1976) Phytochemistry 15:1981-1983
6. e Evans CS. Bell EA (1978) Phytochemistry 17:1127-1129
7. f MeierLK.S0rensen H (1979) Phytochemistry 18:1173-1175
8. Guibé E. Decottignies-Le Maréchal P, Le Maréchal P. Azerad R (1984) FEES Letters 177:265-268
9. 4a PowelGK. Dekker EE ( 1981) Preparative Biochemistry I 1:339-350
10. b Ouerfelli O, Ishida M. Shinozaki H. Nakanishi K. Ohfune Y (1993) Synlett 409-410
11. Panday SK. Griffart-Brunet D, Langlois N (1994) Tetrahedron Lett 35:667-670
12. Ishida M. Akagi H, Shimamoto K. Ohfune Y. Shinozaki H (1990) Brain Res 537:311-314
13. Pook PCK, Jane DE. Jones PLStJ. Tse HW, Watkins JC (1994) Xllth International Congress of Pharmacology. 24-29 July. Montreal. Canada. Poster. P13.2.26
14. E/querra J, Pedregal C, Mice I. Nâjera C (1994) Tetrahedron: Asymmetry 5:921-926; 1867
15. 8a Ethyl pyroglutamate was prepared as described by Silverman RB. Levy M A ( 1980) J Org Chem 45:815-818
16. b The
17. The unsubstituted compound 8 could be hydrolyzed with LiOH at room temperature [71
18. Compound 12a (0.30g, 1.06 mmol) was hydrolyzed with 2.5 M aqueous LiOH (7mL) in THF (8mL) at room temperature for 12 h [7|