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...

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Main Authors: Bentz, E, Goswami, R, Moloney, M, Westaway, S
Format: Journal article
Language:English
Published: 2005
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author Bentz, E
Goswami, R
Moloney, M
Westaway, S
author_facet Bentz, E
Goswami, R
Moloney, M
Westaway, S
author_sort Bentz, E
collection OXFORD
description 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.
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spelling oxford-uuid:2617d893-fbc8-454e-bd52-2206b64e1cf12022-03-26T11:59:02ZStereoselective synthesis of conformationally constrained omega-amino acid analogues from pyroglutamic acid.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:2617d893-fbc8-454e-bd52-2206b64e1cf1EnglishSymplectic Elements at Oxford2005Bentz, EGoswami, RMoloney, MWestaway, SBicyclic 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.
spellingShingle Bentz, E
Goswami, R
Moloney, M
Westaway, S
Stereoselective synthesis of conformationally constrained omega-amino acid analogues from pyroglutamic acid.
title Stereoselective synthesis of conformationally constrained omega-amino acid analogues from pyroglutamic acid.
title_full Stereoselective synthesis of conformationally constrained omega-amino acid analogues from pyroglutamic acid.
title_fullStr Stereoselective synthesis of conformationally constrained omega-amino acid analogues from pyroglutamic acid.
title_full_unstemmed Stereoselective synthesis of conformationally constrained omega-amino acid analogues from pyroglutamic acid.
title_short Stereoselective synthesis of conformationally constrained omega-amino acid analogues from pyroglutamic acid.
title_sort stereoselective synthesis of conformationally constrained omega amino acid analogues from pyroglutamic acid
work_keys_str_mv AT bentze stereoselectivesynthesisofconformationallyconstrainedomegaaminoacidanaloguesfrompyroglutamicacid
AT goswamir stereoselectivesynthesisofconformationallyconstrainedomegaaminoacidanaloguesfrompyroglutamicacid
AT moloneym stereoselectivesynthesisofconformationallyconstrainedomegaaminoacidanaloguesfrompyroglutamicacid
AT westaways stereoselectivesynthesisofconformationallyconstrainedomegaaminoacidanaloguesfrompyroglutamicacid