Stereoselective synthesis of conformationally constrained omega-amino acid analogues from pyroglutamic acid

Bicyclic lactams derived from pyroglutamic acid provide a useful scaffold for synthesis of conformationally restricted analogues of lysine, ornithine and glutamine, as well as an Ala-Ala dipeptide analogue. Amino alcohol and carboxylic acid derivatives are accessible from a common intermediate. In t...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2005-08, Vol.3 (15), p.2872-2882
Main Authors: Bentz, Emilie L, Goswami, Rajesh, Moloney, Mark G, Westaway, Susan M
Format: Article
Language:English
Subjects:
Amino Acids - chemistry
Mass Spectrometry
Molecular Conformation
Pyrrolidonecarboxylic Acid - chemistry
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Bicyclic lactams derived from pyroglutamic acid provide a useful scaffold for synthesis of conformationally restricted analogues of lysine, ornithine and glutamine, as well as an Ala-Ala dipeptide analogue. Amino alcohol and carboxylic acid derivatives are accessible from a common intermediate. In this strategy, the bicyclic lactam system not only controls, but also facilitates the determination of the stereochemistry of the synthetic intermediates.
ISSN:1477-0520
1477-0539
DOI:10.1039/b503994k