Synthesis of medicinally useful lipidicα-amino acids, 2-amino alcohols and diamines.

Abstract:

:The lipidicα-amino acids (LAAs) are non-naturalα-amino acids with saturated or unsaturated long aliphatic side chains. LAAs and their derivatives (lipid mimetics) together with the lipidic peptides represent a class of compounds which combine structural features of lipids with those of amino acids and peptides. Racemic LAAs may be prepared by classical methods and resolved by chemical or enzymatic methods. LAA amides and esters with saturated or unsaturated long chain amines and alcohols respectively, as well as lipidic dipeptide derivatives inhibit both pancreatic and human platelet phospholipase A2. Lipophilic peptide derivatives are inhibitors of human neutrophil elastase. LAAs and their oligomers have been used as drug delivery system. A Lipid-Core-Peptide system has been designed and used as a combined adjuvant-carrier-vaccine system. A variety of lipid mimetics such as lipidic 2-amino alcohols, lipidic 1,2- and 1,3-diamines have been prepared based upon LAAs. Some of them are potent inhibitors of phospholipase A2. A general approach to enantioselective synthesis of LAAs and lipid mimetics is based on the oxidative cleavage of 3-amino-1,2-diols obtained by the regioselective opening of enantiomerically enriched long chain 2,3-epoxy alcohols.

journal_name

Amino Acids

journal_title

Amino acids

authors

Kokotos G,Martin V,Constantinou-Kokotou V,Gibbons WA

doi

10.1007/BF00807940

subject

Has Abstract

pub_date

1996-09-01 00:00:00

pages

329-43

issue

3-4

eissn

0939-4451

issn

1438-2199

journal_volume

11

pub_type

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