Synthesis of Casein-Related Peptides and Phosphopeptides. V. The Efficient Global 'Phosphite-Triester' Phosphorylation of Protected Serine Derivatives and Peptides by Using Dibenzyl or Di-t-butyl N,N-Diethylphosphoramidite
- 1 January 1990
- journal article
- research article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 43 (10) , 1623-1632
- https://doi.org/10.1071/ch9901623
Abstract
Both dibenzyl N,N- diethylphosphoramidite and di -t-butyl N,N- diethylphosphoramidite are shown to be suitable reagents for the efficient 1H-tetrazole-catalysed 'phosphite-triester' phosphorylation of the protected serine derivative Boc-Ser-OCH2C6H4NO2-p. Both these reagents were also used for the phosphorylation of the protected serine derivative Boc-Glu ( OBut )-Ser- Leu-OBut, and subsequent hydrogenolytic treatment of Boc-Glu ( OBut )-Ser(PO3Bzl2)- Leu-OBut or acidolytic treatment of Boc-Glu ( OBut )-Ser(PO3But2)- Leu-OBut gave the O- phosphoseryl tripeptide Glu -Ser(PO3H2)- Leu in near-quantitive yield.Keywords
This publication has 2 references indexed in Scilit:
- Synthesis of Casein-Related Peptides and Phosphopeptides. IV. Phosphorotriester and 'Phosphite-Triester' Phosphorylation of Protected Serine-Containing PeptidesAustralian Journal of Chemistry, 1990
- Active esters of 9-fluorenylmethyloxycarbonyl amino acids and their application in the stepwise lengthening of a peptide chainThe Journal of Organic Chemistry, 1980