Potential peptidic proteasome inhibitors by incorporation of an electrophilic trap based on amino acid derived α-substituted sulfonyl fluorides

Herrero Alvarez, N., Van De Langemheen, H., Brouwer, A. J. and Liskamp, R. M.J. (2017) Potential peptidic proteasome inhibitors by incorporation of an electrophilic trap based on amino acid derived α-substituted sulfonyl fluorides. Bioorganic and Medicinal Chemistry, 25(19), pp. 5055-5063. (doi: 10.1016/j.bmc.2017.07.019) (PMID:28734665)

Abstract

Peptido sulfonyl fluoride derivatives were designed and synthesized containing a substituent on the alpha position (αPSFs) with respect to the sulfonyl fluoride electrophilic trap. The chemical reactivity of these α-substituted amino sulfonyl fluorides was studied and compared with the previously described β-substituted amino sulfonyl fluorides in order to get a deeper insight into the importance of the immediate structural environment of the sulfonyl fluoride moiety. Unfortunately, the poor solubility of the resulting αPSFs precluded a proper evaluation of their biological activity.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Liskamp, Professor Robert and Herrero Alvarez, Natalia and Van De Langemheen, Mr Helmus
• Authors: Herrero Alvarez, N., Van De Langemheen, H., Brouwer, A. J., and Liskamp, R. M.J.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Bioorganic and Medicinal Chemistry
• Publisher: Elsevier
• ISSN: 0968-0896
• ISSN (Online): 1464-3391
• Published Online: 12 July 2017
• Copyright Holders: Copyright © 2017 Elsevier Ltd.
• First Published: First published in Bioorganic and Medicinal Chemistry 25(19):5055-5063
• Publisher Policy: Reproduced in accordance with the copyright policy of the publisher