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Lipidic peptides, I. Synthesis, resolution and structural elucidation of lipidic amino acids and their homo‐ and hetero‐oligomers
Author(s) -
Gibbons William A.,
Hughes Richard A.,
Charalambous Mario,
Christodoulou Marika,
Szeto Alice,
Aulabaugh Anne E.,
Mascagni Paolo,
Toth Istvan
Publication year - 1990
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.1990199001215
Subject(s) - chemistry , amino acid , side chain , diastereomer , alkyl , carbodiimide , peptide , stereochemistry , resolution (logic) , organic chemistry , combinatorial chemistry , biochemistry , polymer , artificial intelligence , computer science
The α‐amino acids with long alkyl side chains, the so‐called lipidic amino acids 1a – e , and their homo‐oligomers, the lipidic peptides 1p – aj , represent a class of compounds which combine the structural properties of peptides and proteins with the characteristics of lipids and membranes. The amino acids were synthesised from the appropriate alkyl bromide and diethyl acetamidomalonate. Resolution was made chemically, by forming diastereomers of the amino acid esters with an optically pure α‐pinene derivative. The protected homooligomers were synthesised in solution with the assistance of a water‐soluble carbodiimide coupling agent. In order to modify the physical and chemical properties of the peptides, a series of protected hetero‐oligomers were prepared, by similar methods, incorporating either other amino acids ( 3a – d , 7a – i ) or side‐chain‐substituted lipidic amino acids ( 6a – d ).