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D(−)- and L(+)-γ-Carboxyglutamic Acid (Gla): Resolution of Synthetic Gla Derivatives

✍ Scribed by Walter Märki; Max Oppliger; Peter Thanei; Robert Schwyzer

Publisher
John Wiley and Sons
Year
1977
Tongue
German
Weight
509 KB
Volume
60
Category
Article
ISSN
0018-019X

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✦ Synopsis

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.

📜 SIMILAR VOLUMES

Chemical Synthesis, Proton NMR. Paramete
Chemical Synthesis, Proton NMR. Parameters, Hydrogen- and Calcium-Ion. Complexation of L-γ-Carboxyglutamyl-L-γ-carboxyglutamic Acid and D-γ-Carboxyglutamyl-L-leucine
✍ Walter Märki; Max Oppliger; Robert Schwyzer 📂 Article 📅 1977 🏛 John Wiley and Sons 🌐 German ⚖ 495 KB

## Abstract The purpose of this communication is to describe the preparation and some properties of the first two synthetic peptides containing D‐ and L‐γ‐carboxyglutamic acid. Use was made of __N__‐protected γ,γ′‐di‐__t__‐butyl‐γ‐carboxyglutamic acids (D, L, and DL) described earlier [1 a]. Prelim