Literature DB >> 23489632

Photoinitiated release of an aziridinium ion precursor for the temporally controlled alkylation of nucleophiles.

Stephen T McCarron1, Mariel Feliciano, Jeffreys N Johnson, James J Chambers.   

Abstract

A photo-activatable aziridinium precursor has been developed to investigate the possibility of a photo-initiated traditional nucleophilic reaction. The photolysis of a quaternary amine yields a tertiary amine and has allowed us to temporally control aziridinium formation and subsequent alkylation of a colorimetric nucleophilic reporter molecule. We have also used this photo-initiated reaction to alkylate a sulfhydryl group. This new photo-initiated alkylation strategy is water-soluble and expands the toolkit of photo-activated crosslinkers for protein labeling research. Published by Elsevier Ltd.

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Year:  2013        PMID: 23489632      PMCID: PMC3609034          DOI: 10.1016/j.bmcl.2013.02.044

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  29 in total

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Review 5.  New photolabeling and crosslinking methods.

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Review 6.  Potential of the NBP method for the study of alkylation mechanisms: NBP as a DNA-model.

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Review 8.  Benzophenone photophores in biochemistry.

Authors:  G Dormán; G D Prestwich
Journal:  Biochemistry       Date:  1994-05-17       Impact factor: 3.162

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Journal:  Mol Pharmacol       Date:  1982-03       Impact factor: 4.436

10.  Use of 4-(nitrobenzyl)pyridine (4-NBP) to test mutagenic potential of slow-reacting epoxides, their corresponding olefins, and other alkylating agents.

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  1 in total

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Journal:  Nat Methods       Date:  2018-03-26       Impact factor: 28.547

  1 in total

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