The triphenylphosphine-sulfur trioxide adduct as a coupling reagent in peptide synthesis

Several adducts of sulfur trioxide with electron-donor molecules have been prepared. Of these the air-stable triphenylphosphine-SO 3 complex has been shown to be the most useful in the synthesis of peptides. It has been demonstrated that a variety of solvents may be used for couplings, but that in o...

Full description

Saved in:
Bibliographic Details
Published in:Bioorganic chemistry 1979-01, Vol.8 (3), p.323-332
Main Authors: Galpin, I.J., Kenner, G.W., Marston, A.
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Several adducts of sulfur trioxide with electron-donor molecules have been prepared. Of these the air-stable triphenylphosphine-SO 3 complex has been shown to be the most useful in the synthesis of peptides. It has been demonstrated that a variety of solvents may be used for couplings, but that in order for reaction to occur the solvent must itself be able to form an adduct. This behaviour is due to the fact that SO 3 is transferred from the triphenylphosphine-SO 3 complex to the solvent, thus forming an intermediate complex which is responsible for activation of the carboxylate unit. The carboxyl component is generally present as its tetramethylguanidinium salt. The method has been used to synthesize several model peptides and to prepare a fully biologically active sample of methionine-enkephalin.
ISSN:0045-2068
1090-2120
DOI:10.1016/0045-2068(79)90059-2