Process for synthesizing L-γ-methylene glutamic acid...

Details Process for synthesizing L-γ-methylene glutamic acid... Process for synthesizing L-γ-methylene glutamic acid...

2005-12-20

2005-12-20

Tsang, Cecilia J. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

C562S573000, C548S472000

Reexamination Certificate

active

06977311

ABSTRACT:
A process for synthesizing substantially enantiomerically pure L-amino acids, particularly L-γ-methylene glutamic acid, and esters and salts thereof. The process includes the derivatization of (2S)-pyroglutamic acid, and the decyclization of the resulting derivative to form the desired end product.

REFERENCES:
patent: 4996207 (1991-02-01), Nair et al.
patent: 5550128 (1996-08-01), Nair et al.
Ezquerra et al , Efficient synthesis of 4-methylene-L-glutamic acid and its cyclopropyl analog, 1994, 5(5), p. 921-6.
Kristensen et al., “Synthesis and Properties of Hydroxylated and Alkylated Acidic Amino Acids, Especially Glutamic Acid”ACTA Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, B34(7):497-504 (1980).
Powell et al., “A Modified High Yield Procedure for the Synthesis of Unlabeled and Carbon 14-Labeled 4-Methylene-DL-Glutamic Acid,”Preparative Biochemistry, 11(3):339-350 (1981); and.
Boggs et al., “Chemical Modification of Peptides Containing alpha-Carboxyglutamic Acid,”J. Org. Chem., 47(10):1812-1816 (1982).

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