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

Research output: Contribution to journalArticleResearchpeer-review

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.

LanguageEnglish
Pages7452-7455
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number42
DOIs
Publication statusPublished - 15 Oct 2007

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Catalysis
Hydrolysis
Acids
Buffers
Post Translational Protein Processing
Least-Squares Analysis
Amides
Phosphates
Water
Proteins

Cite this

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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.",
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Hydrolysis rates of alkyl and aryl sulfinamides : evidence of general acid catalysis. / Piggott, Andrew M.; Karuso, Peter.

In: Tetrahedron Letters, Vol. 48, No. 42, 15.10.2007, p. 7452-7455.

Research output: Contribution to journalArticleResearchpeer-review

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