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A new synthetic equivalent of the glutamic acid γ-anion and its application to the synthesis of S-(+)-γ-carboxyglutamic acid.

✍ Scribed by Michael R. Attwood; Maria G. Carr; Steven Jordan

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
128 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis

Protected S-pyroglutamic acid can be deprotonated specifically at the y-position. The resulting enolate can be converted into y-carboxyglutamic acid in optically pure form. The naturally occurring aminoacid r_carboxyglutamtc acid (1; Gla) is a constituent of prothrombin and other proteins.1 The natural enantiomer of this aminoacid has been prepared both by resolution2b and by elaboration of S-glutamic acid (S-Glu) derivatives involving anion formation at the y-position with retention of configuration at the a-centre.41S The y-anion synthon (2) is also of interest for the generation of other

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