Hydrolysis rates of alkyl and aryl sulfinamides: evidence of general acid catalysis

Piggott, Andrew M. and Karuso, Peter (2007) Hydrolysis rates of alkyl and aryl sulfinamides: evidence of general acid catalysis. Tetrahedron letters, 48 42: 7452-7455. doi:10.1016/j.tetlet.2007.08.081


Author Piggott, Andrew M.
Karuso, Peter
Title Hydrolysis rates of alkyl and aryl sulfinamides: evidence of general acid catalysis
Journal name Tetrahedron letters   Check publisher's open access policy
ISSN 0040-4039
Publication date 2007-10-15
Year available 2007
Sub-type Article (original research)
DOI 10.1016/j.tetlet.2007.08.081
Volume 48
Issue 42
Start page 7452
End page 7455
Total pages 4
Place of publication Oxford
Publisher Pergamon Press
Language eng
Subject 0305 Organic Chemistry
Abstract Sulfinamides are important in enantioselective synthesis, as rare post-translational modifications of proteins and as isosteres of the amide bond. Little is known about the rates of hydrolysis for aliphatic sulfinamides or the mechanism of hydrolysis. In this Letter, we show that sulfinamides hydrolyse by predominantly a non-specific acid/base catalysis with phosphate buffer but by varying the buffer concentration, it was possible to determine the hydrolysis rates of a range of sulfinamides with water through non-linear least squares regression
Keyword Sulfinamide
Hydrolysis
Non-specific acid/base catalysis
Enzyme inhibitors
Q-Index Code C1

Document type: Journal Article
Sub-type: Article (original research)
Collections: Excellence in Research Australia (ERA) - Collection
Institute for Molecular Bioscience - Publications
 
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Created: Wed, 21 Jan 2009, 20:05:37 EST by Ms Lynette Adams on behalf of Institute for Molecular Bioscience