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Synthesis and application of photoproline - a photoactivatable derivative of proline


VanderMeijden, B; Robinson, J A (2011). Synthesis and application of photoproline - a photoactivatable derivative of proline. Arkivoc, 2011(vi):130-136.

Abstract

A convenient synthesis in optically pure form of a derivative of L-proline is described, called photoproline, containing a diazirine group at position-4 of the pyrrolidine ring, starting from L-4-hydroxyproline. The use of Fmoc-L-photoproline in the synthesis of a cyclic peptidomimetic antibiotic demonstrates that this photoprobe can be incorporated into synthetic peptides using solid-phase Fmoc chemistry. Photoproline may be of wide value in the preparation of diverse peptide-based photoaffinity probes.

Abstract

A convenient synthesis in optically pure form of a derivative of L-proline is described, called photoproline, containing a diazirine group at position-4 of the pyrrolidine ring, starting from L-4-hydroxyproline. The use of Fmoc-L-photoproline in the synthesis of a cyclic peptidomimetic antibiotic demonstrates that this photoprobe can be incorporated into synthetic peptides using solid-phase Fmoc chemistry. Photoproline may be of wide value in the preparation of diverse peptide-based photoaffinity probes.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2011
Deposited On:08 Jan 2012 12:24
Last Modified:05 Apr 2016 15:19
Publisher:Arkat USA Inc
ISSN:1551-7004
Funders:SNF
Additional Information:ARKIVOC Volume 2011, Part (vi): Commemorative Issue in Honor of Prof. Heinz Heimgartner on the occasion of his 70th anniversary.
Official URL:http://www.arkat-usa.org/get-file/37261/
Related URLs:http://www.arkat-usa.org (Publisher)

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