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Issue 4, 2014
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Arsinous acid as a thiol binding group: potential cysteine peptide tagging functionality that binds a single thiol

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Abstract

A simple aryl arsinous acid (ArAs(CH3)OH) was prepared by ortho mercuration of p-cresol followed by Pd-catalyzed reaction with methylarsenic dibromide, purification as the mercaptoethanol adduct, and deprotection using a silver salt. Isothermal titration calorimetry experiments showed reaction with mercaptoethanol with an association constant of 6 × 104 M−1. Rapid exchange of thiols at the arsenic atom was demonstrated by 1H-NMR.

Graphical abstract: Arsinous acid as a thiol binding group: potential cysteine peptide tagging functionality that binds a single thiol

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Publication details

The article was received on 22 Nov 2013, accepted on 07 Jan 2014 and first published on 09 Jan 2014


Article type: Letter
DOI: 10.1039/C3NJ01462B
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New J. Chem., 2014,38, 1368-1371

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    Arsinous acid as a thiol binding group: potential cysteine peptide tagging functionality that binds a single thiol

    X. Liang and D. G. Drueckhammer, New J. Chem., 2014, 38, 1368
    DOI: 10.1039/C3NJ01462B

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