Synthesis of Peptides with α,β‐Dehydroamino Acids, III. Debenzyloxycarbonylation and Detrifluoroacetylation of Dehydroalanine and Dehydrophenylalanine Peptides | Zendy

Makowski Maciej | Zendy; Rzeszotarska Barbara | Zendy; Smelka Leszek | Zendy; Kubica Zbigniew | Zendy

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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).

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