Issue 7, 2017

Synthesis and characterization of photoaffinity labelling reagents towards the Hsp90 C-terminal domain

Abstract

Glucosyl-novobiocin-based diazirine photoaffinity labelling reagents (PALs) were designed and synthesized to probe the Hsp90 C-terminal domain unknown binding pocket and the structure–activity relationship. Five PALs were successfully synthesized from novobiocin in six consecutive steps employing phase transfer catalytic glycosylation. Reactions were monitored and guided by analytical LC/MS which led to different strategies of adding either a PAL precursor or a sugar moiety first. The structures and bonding linkages of these compounds were characterised by various 2D-NMR spectroscopy and MS techniques. Synthetic techniques provide powerful probes for unknown protein binding pockets.

Graphical abstract: Synthesis and characterization of photoaffinity labelling reagents towards the Hsp90 C-terminal domain

Supplementary files

Article information

Article type
Paper
Submitted
26 Sep 2016
Accepted
05 Dec 2016
First published
05 Dec 2016

Org. Biomol. Chem., 2017,15, 1597-1605

Synthesis and characterization of photoaffinity labelling reagents towards the Hsp90 C-terminal domain

B. Simon, X. Huang, H. Ju, G. Sun and M. Yang, Org. Biomol. Chem., 2017, 15, 1597 DOI: 10.1039/C6OB02097F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements