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Synthesis of Peptides with α,β‐Dehydroamino Acids, III. Debenzyloxycarbonylation and Detrifluoroacetylation of Dehydroalanine and Dehydrophenylalanine Peptides
Author(s) -
Makowski Maciej,
Rzeszotarska Barbara,
Smelka Leszek,
Kubica Zbigniew
Publication year - 1985
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198519850716
Subject(s) - dehydroalanine , chemistry , stereochemistry , amino acid , peptide , protecting group , combinatorial chemistry , biochemistry , organic chemistry , alkyl
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 is interesting to note that from the Δ Ala peptides, the Z group can be split off in preparative manner with HCO 2 NH 4 in the presence of Pd C (Table 4).