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Phosphoramidate‐peptide synthesis by solution‐ and solid‐phase Staudinger‐phosphite reactions
Author(s) -
Serwa Remigiusz A.,
Swiecicki JeanMarie,
Homann Denise,
Hackenberger Christian P. R.
Publication year - 2010
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.1236
Subject(s) - phosphoramidate , chemistry , peptide , combinatorial chemistry , staudinger reaction , solid phase synthesis , peptide synthesis , aryl , sequence (biology) , organic chemistry , stereochemistry , biochemistry , alkyl
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.