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)

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: Jamieson, Professor Andrew and Hoose, Mr Alex and Knuhtsen, Dr Astrid 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