Synthesis of pyrazole containing α-amino acids via a highly regioselective condensation/aza-Michael reaction of β-aryl α,β-unsaturated ketones

Gilfillan, L., Artschwager, R., Harkiss, A. H., Liskamp, R. M.J. and Sutherland, A. (2015) Synthesis of pyrazole containing α-amino acids via a highly regioselective condensation/aza-Michael reaction of β-aryl α,β-unsaturated ketones. Organic and Biomolecular Chemistry, 13(15), pp. 4514-4523. (doi:10.1039/C5OB00364D) (PMID:25774874)

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Abstract

A synthetic approach for the preparation of a new class of highly conjugated unnatural α-amino acids bearing a 5-arylpyrazole side-chain has been developed. Horner–Wadsworth–Emmons reaction of an aspartic acid derived β-keto phosphonate ester with a range of aromatic aldehydes gave β-aryl α,β-unsaturated ketones. Treatment of these with phenyl hydrazine followed by oxidation allowed the regioselective synthesis of pyrazole derived α-amino acids. As well as evaluating the fluorescent properties of the α-amino acids, their synthetic utility was also explored with the preparation of a sulfonyl fluoride derivative, a potential probe for serine proteases.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Sutherland, Dr Andrew and Liskamp, Professor Robert and Gilfillan, Miss Lynne and Harkiss, Mr Alexander and Artschwager, Raik
Authors: Gilfillan, L., Artschwager, R., Harkiss, A. H., Liskamp, R. M.J., and Sutherland, A.
College/School:College of Medical Veterinary and Life Sciences
College of Science and Engineering > School of Chemistry
Journal Name:Organic and Biomolecular Chemistry
Publisher:Royal Society of Chemistry
ISSN:1477-0520
ISSN (Online):1477-0539
Published Online:10 March 2015
Copyright Holders:Copyright © 2015 The Royal Society of Chemistry
First Published:First published in Organic and Biomolecular Chemistry 13(15):4514-4523
Publisher Policy:Reproduced under a Creative Commons License

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
608951Engineering and Physical Sciences Doctoral Training Grant 2012-16Mary Beth KneafseyEngineering & Physical Sciences Research Council (EPSRC)EP/K503058/1VICE PRINCIPAL RESEARCH & ENTERPRISE