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Lipidic peptides, VII. Synthesis and structure elucidation of γ‐aminobutyric acid conjugates with lipidic acids, lipidic amino acids and lipidic peptides
Author(s) -
Hussain Rohanah,
Toth Istvan,
Gibbons William A.
Publication year - 1991
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.1991199101165
Subject(s) - chemistry , amino acid , peptide , amide , conjugate , aminobutyric acid , stereochemistry , biochemistry , receptor , mathematical analysis , mathematics
Abstract A series of γ‐aminobutyric acid esters of lipidic acids, lipidic peptides and γ‐aminobutyric acid amides of lipidic α‐amino acids and oligomers were synthesised. The GABA conjugates with ester linkages ( 6j–r ) were prepared by coupling the lipidic acids and peptide conjugates to the carboxyl terminus of GABA. Two types of GABA conjugates linked by amide bonds were synthesised. This class included compounds 5d–f in which the amino group of the lipidic amino acid is condensed with the carboxyl function of GABA and compounds 7a–b with the carboxyl terminus of the α‐amino acid coupled to the amino group of GABA. The lipidic amino acid peptide oligomers were varied from 1–3 units, and the alkyl side chains ranged from 5–17 carbon atoms in length in order to impart different lipophilicities to the GABA molecule conjugates.