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D (−)‐ and L (+)‐γ‐Carboxyglutamic Acid (Gla): Resolution of Synthetic Gla Derivatives
Author(s) -
Märki Walter,
Oppliger Max,
Thanei Peter,
Schwyzer Robert
Publication year - 1977
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19770600310
Subject(s) - chemistry , derivative (finance) , decarboxylation , salt (chemistry) , enantiomer , resolution (logic) , stereochemistry , glutamic acid , amino acid , organic chemistry , biochemistry , artificial intelligence , computer science , financial economics , economics , catalysis
Abstract The chemical resolution of γ,γ′‐di‐ t ‐butyl DL ‐ N ‐benzyloxycarbonyl‐γ‐carboxy‐glutamate is described in detail (preliminary account see [1]). The D (−)‐derivative was obtained as a crystalline quinine salt, and the L (+)‐derivative as a crystalline salt with (−)‐ephedrine in yields of 44 and 70%, respectively. Physical data are indicated for the enantiomers of γ,γ′‐di‐ t ‐butyl N ‐benzyloxycarbonyl‐γ‐carboxyglutamate, γ,γ′‐di‐ t ‐butyl γ‐carboxyglutamate, and γ‐carboxyglutamic acid. The absolute configurations and optical purities of the γ,γ′‐di‐ t ‐butyl (+)‐ and (−)‐ N ‐benzyloxycarbonyl‐γ‐carboxyglutamates were determined by removal of the protecting groups and decarboxylation to optically active glutamic acid.