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

Simon, B; Huang, X; Ju, H; Sun, G; Yang, M; (2017) Synthesis and characterization of photoaffinity labelling reagents towards the Hsp90 C-terminal domain. Organic & Biomolecular Chemistry (7) pp. 1597-1605. 10.1039/c6ob02097f. Green open access

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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.

Type: Article
Title: Synthesis and characterization of photoaffinity labelling reagents towards the Hsp90 C-terminal domain
Location: England
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/c6ob02097f
Publisher version: http://dx.doi.org/10.1039/c6ob02097f
Language: English
Additional information: This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions.
UCL classification: UCL
UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences
URI: https://discovery.ucl.ac.uk/id/eprint/1536384
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