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Phosphoramidate-peptide synthesis by solution- and solid-phase Staudinger-phosphite reactions

✍ Scribed by Remigiusz A. Serwa; Jean-Marie Swiecicki; Denise Homann; Christian P. R. Hackenberger

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
267 KB
Volume
16
Category
Article
ISSN
1075-2617

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✦ Synopsis

Abstract

The chemoselective incorporation of phosphoramidate moieties into peptides by a Staudinger‐phosphite reaction of azides can be performed in many solvents, including water. In this report, we present two strategies for an efficient synthesis of phosphoramidate‐containing peptides, in which the Staudinger‐phosphite reaction is performed either on the solid support or in solution with aryl azido‐containing peptides. The corresponding Staudinger reactions proceed in high conversion rates and deliver phosphoramidate peptides, in which the modification site is located in the middle of the peptide sequence. Copyright © 2010 European Peptide Society and John Wiley & Sons, Ltd.

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