Evaluation of vinylsulfamides as sulfhydryl selective alkylation reagents in protein modification

Li, Min; Wu, Robert S.; Tsai, Jane; Salamone, Salvatore J.

doi:10.1016/s0960-894x(02)00950-2

Bioorganic & Medicinal Chemistry Letters

2003

DOI: 10.1016/s0960-894x(02)00950-2

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Evaluation of vinylsulfamides as sulfhydryl selective alkylation reagents in protein modification

Min Li

Robert S. Wu

Jane Tsai

et al.

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Cited by 7 publications

(1 citation statement)

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“…It was also decided to prepare the simpler and more easily accessible sulfonamide 1 to conduct some model studies on reactivity. Using a modification of a procedure reported by Li et al, 18 the synthesis of vinylsulfonamide 1 was accomplished, in a one-pot reaction, from commercially available 2-chloroethanesulfonyl chloride. In our hands, the most convenient procedure involved the addition of chloroethanesulfonyl chloride to a solution of amylamine in dichloromethane in the presence of triethylamine at room temperature (Scheme 1).…”

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3,2-Hydroxypyridinone (3,2-HOPO) vinyl sulfonamide and acrylamide linkers: aza-Michael addition reactions and the preparation of poly-HOPO chelators

Martı́nez

Jayanthi

Jacobs

et al. 2013

Tetrahedron Letters

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The HOPO vinyl sulfonamide 3 and the corresponding HOPO acrylamide 10, were easily prepared by short synthetic sequences. Investigation of the aza-Michael reactions of these linkers showed that they proceed at a higher rate in solvent systems containing water. The scope and limits of the aza-Michael reactions of 3 and 10 were examined. Reagents 3 and 10 reacted cleanly with piperazine to give the corresponding adducts which were deprotected to give the di-HOPO ligands 7 and 16. Reaction of HOPO acrylamide 10 with 1,4,7-triazacyclononane gave the tris-adduct 17 which was deprotected to give the desired tris-HOPO ligand 18. Overall, the aza-Michael reactions of 3 and 10 appear to be governed not only by the solvent but also by the nature of the amine and the solubility of the reaction intermediates.

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confidence: 99%

3,2-Hydroxypyridinone (3,2-HOPO) vinyl sulfonamide and acrylamide linkers: aza-Michael addition reactions and the preparation of poly-HOPO chelators

Martı́nez

Jayanthi

Jacobs

et al. 2013

Tetrahedron Letters

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Evaluation of Vinylsulfamides as Sulfhydryl Selective Alkylation Reagents in Protein Modification.

Tsai

et al. 2003

ChemInform

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SulfonamidesSulfonamides P 0410 Evaluation of Vinylsulfamides as Sulfhydryl Selective Alkylation Reagents in Protein Modification. -Several model vinylsulfamides (III) are prepared from 2-chloroethanesulfonyl chloride (I). They show excellent selectivity towards sulfhydryl group relative to amino group. -(LI*, M.; WU, R. S.; TSAI, J. S. C.; SALAMONE, S. J.; Bioorg. Med. Chem. Lett. 13 (2003) 3, 383-386; Roche Diagn. Corp., Indianapolis, IN 46250, USA; Eng.) -R. Langenstrassen 22-072

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Kinetic Template‐Guided Tethering of Fragments

2012

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This thesis is composed of two separate projects: Kinetic Template-Guided Tethering of Fragments and Design and Synthesis of a Chemical Probe to Dissect the Cellular Signalling Cascade leading to Cyclin D1 Degradation after DNA Damage. Kinetic Template-Guided Tethering of FragmentsThe development of a novel methodology for the site-directed discovery of small molecule, protein-binding ligands is described. The protein of interest, with a cysteine thiol (either native or engineered) adjacent to the desired binding pocket, is incubated with mixtures of low molecular weight compounds (fragments) modified with either an acrylamide or a vinyl sulfonamide capture group. Any ligand within the mixture that binds within the pocket brings the capture group into close proximity with the cysteine thiol, promoting a conjugate addition reaction at an increased rate over the background reaction. The capture reaction is designed to be slow, such that during the time course of an experiment, no adduct formation is observed unless the reaction is templated by the protein. By this method, binding ligands are rapidly identified by mass spectrometry analysis of the crude reaction mixtures. The methodology has been termed 'kinetic template-guided tethering'. Design and Synthesis of a Chemical Probe to Dissect the Cellular Signalling Cascade leading to Cyclin D1Degradation after DNA Damage An inhibitor described within the literature was found to attenuate the reduction of cyclin D1 after DNA damage to cells. In order to implement a two-step chemical proteomics strategy to find the molecular target of this inhibitor, a synthesis of the compound with an alkyne appendage was required. The alkyne acts as a functional handle for attachment of a reporter molecule in cells via the Huisgen cycloaddition ('Click') reaction. The design and synthesis of this inhibitor with the alkyne appendage is described.

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Evaluation of vinylsulfamides as sulfhydryl selective alkylation reagents in protein modification

Cited by 7 publications

References 10 publications

3,2-Hydroxypyridinone (3,2-HOPO) vinyl sulfonamide and acrylamide linkers: aza-Michael addition reactions and the preparation of poly-HOPO chelators

3,2-Hydroxypyridinone (3,2-HOPO) vinyl sulfonamide and acrylamide linkers: aza-Michael addition reactions and the preparation of poly-HOPO chelators

Evaluation of Vinylsulfamides as Sulfhydryl Selective Alkylation Reagents in Protein Modification.

Kinetic Template‐Guided Tethering of Fragments

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