Literature DB >> 17107047

Spin-trapping of the p-benzyne intermediates from ten-membered enediyne calicheamicin gamma1I.

Toyonobu Usuki1, Koji Nakanishi, George A Ellestad.   

Abstract

In the presence of thiols, the ten-membered-ring enediyne calicheamicin gamma1I generates a p-benzyne biradical that initiates oxidative cleavage of double-stranded DNA. Application of spin-trapping has successfully provided ESR and mass spectroscopic evidence for the formation of the monoadducts with phenyl tert-butyl nitrone (PBN). [reaction: see text].

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Year:  2006        PMID: 17107047     DOI: 10.1021/ol062061t

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Efficient and accurate characterization of the Bergman cyclization for several enediynes including an expanded substructure of esperamicin A1.

Authors:  Edward C Sherer; Karl N Kirschner; Frank C Pickard; Chantelle Rein; Steven Feldgus; George C Shields
Journal:  J Phys Chem B       Date:  2008-12-25       Impact factor: 2.991

2.  An ESR analysis of the mechanism of pericyclic reactions of bicyclobutane.

Authors:  Maciej A A Walczak; Byong-Kyu Shin; Peter Wipf; Sunil Saxena
Journal:  Org Biomol Chem       Date:  2009-04-06       Impact factor: 3.876

3.  Synthesis of N-arylpyridinium salts bearing a nitrone spin trap as potential mitochondria-targeted antioxidants.

Authors:  Linsey Robertson; Richard C Hartley
Journal:  Tetrahedron       Date:  2009-07-04       Impact factor: 2.457

  3 in total

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