The H-phosphonate approach to the synthesis of phosphopeptides on solid phase

Citation
Z. Kupihar et al., The H-phosphonate approach to the synthesis of phosphopeptides on solid phase, ORG LETT, 3(7), 2001, pp. 1033-1035
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
7
Year of publication
2001
Pages
1033 - 1035
Database
ISI
SICI code
1523-7060(20010405)3:7<1033:THATTS>2.0.ZU;2-Z
Abstract
Ammonium tert-butyl H-phosphonate was used for the phosphorylation of Tyr- and Ser-containing peptides synthesized by an Fmoc strategy. This reaction, leading to a monoprotected peptide phosphate, was found to be highly effic ient and generally applicable. Moreover, the method employed avoids undesir ed side reactions during chain elongation (pyrophosphate formation and beta -elimination catalyzed by piperidine).