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 CH3COO2H. α,β-Dideuterated tryptophan was in turn synthetized from ethyl-α-acetamido-indole-3-acrylate, by catalytic deuteration (2H2/Pd-C) and alkaline hydrolysis (NaO2H/2H2O).
Synthesis of (2R,S)-[2-2H] and [2,3-2H] tryptophan / E. Santaniello, M. Ravasi, F. Astori. - In: JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS. - ISSN 0362-4803. - 19:4(1982), pp. 611-617.
Synthesis of (2R,S)-[2-2H] and [2,3-2H] tryptophan
E. SantanielloPrimo
;
1982
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 CH3COO2H. α,β-Dideuterated tryptophan was in turn synthetized from ethyl-α-acetamido-indole-3-acrylate, by catalytic deuteration (2H2/Pd-C) and alkaline hydrolysis (NaO2H/2H2O).
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