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)
|
Text
104360.pdf - Published Version Available under License Creative Commons Attribution. 390kB |
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: | Liskamp, Professor Robert and Harkiss, Dr Alexander and Haahr, Dr Lynne and Sutherland, Professor Andrew 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 |
University Staff: Request a correction | Enlighten Editors: Update this record