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Synthesis of (2R,S)- [2-2H] and [2,3-2H] tryptophan

✍ Scribed by Enzo Santaniello; Manuela Ravasi; Franca Astori

Publisher
John Wiley and Sons
Year
1982
Tongue
French
Weight
278 KB
Volume
19
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

α‐Deuterated tryptophan was prepared either by exchange of the α‐hydrogen of tryptophan or by hydrolysis and decarboxylation of ethyl 2‐formamido‐2‐carbethoxy‐3‐indole propionate, followed by treatment with CH~3~COO^2^H. α,β‐Dideuterated tryptophan was in turn synthetized from ethyl‐α‐acetamido‐indole‐3‐acrylate, by catalytic deuteration (^2^H~2~/Pd‐C) and alkaline hydrolysis (NaO^2^H/^2^H~2~O).

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