Solid-phase synthesis of oxetane modified peptides

Beadle, J. D., Knuhtsen, A., Hoose, A., Raubo, P., Jamieson, A. G. and Shipman, M. (2017) Solid-phase synthesis of oxetane modified peptides. Organic Letters, 19(12), pp. 3303-3306. (doi: 10.1021/acs.orglett.7b01466) (PMID:28585839)

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Abstract

Solid-phase peptide synthesis (SPPS) is used to create peptidomimetics in which one of the backbone amide C═O bonds is replaced by a four-membered oxetane ring. The oxetane containing dipeptide building blocks are made in three steps in solution, then integrated into peptide chains by conventional Fmoc SPPS. This methodology is used to make a range of peptides in high purity including backbone modified derivatives of the nonapeptide bradykinin and Met- and Leu-enkephalin.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Knuhtsen, Dr Astrid and Jamieson, Dr Andrew and Hoose, Mr Alex and Shipman, Mr Michael
Authors: Beadle, J. D., Knuhtsen, A., Hoose, A., Raubo, P., Jamieson, A. G., and Shipman, M.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Organic Letters
Publisher:American Chemical Society
ISSN:1523-7060
ISSN (Online):1523-7052
Published Online:06 June 2017
Copyright Holders:Copyright © 2017 The American Chemical Society
First Published:First published in Organic Letters 19(12):3303-3306
Publisher Policy:Reproduced in accordance with the copyright policy of the publisher

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