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Synthesis of Peptides with α,β-Dehydroamino Acids, I. Synthesis ofN-Benzyloxycarbonyl andN-Trifluoroacetyl Dipeptides of Dehydroalanine and Dehydrophenylalanine

✍ Scribed by Makowski, Maciej ;Rzeszotarska, Barbara ;Kubica, Zbigniew ;Wieczorek, Piotr

Publisher
John Wiley and Sons
Year
1984
Tongue
English
Weight
475 KB
Volume
1984
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Condensation of amides of N‐(benzyloxycarbonyl)‐ and N‐(trifluoroacetyl)amino acid with pyruvic and phenylpyruvic acid yields, in the presence of p‐toluenesulfonic acid as a catalyst, N‐(benzyloxycarbonyl)‐ and N‐(trifluoroacetyl)dehydro dipeptides with C‐terminal Δ Ala and ΔPhe, respectively (Table 2 and 3).

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## Abstract The removal of amino protecting groups from a series of twelve model Z‐^3)^ or TFA‐dipeptides of dehydroalanine and (Z)‐dehydrophenylalanine was investigated. During this deprotection, peptides with Δ Ala are prone to side reactions to a higher extent than those with Δ Phe. Therefore it