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The DNA phosphate backbone is not involved in catalysis of the duocarmycin and CC-1065 DNA alkylation reaction

Academic Article
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Overview

authors

  • Ambroise, Y.
  • Boger, Dale

publication date

  • February 2002

journal

  • Bioorganic & Medicinal Chemistry Letters  Journal

abstract

  • The rates of DNA alkylation were established for the reaction of (+)-duocarmycin SA (1) with the native duplex d(G(1)TCAATTAGTC(11))*d(G(12)ACTAATTGAC(22)), an 11 bp deoxyoligonucleotide that contains a single high-affinity alkylation site that has been structurally characterized at exquisite resolution, and modified duplexes in which the four backbone phosphates proximal to the C4 carbonyl of bound 1 were replaced with methylphosphonates. All were found to react at comparable rates establishing that these backbone phosphates do not participate in catalysis of the DNA alkylation reaction.

subject areas

  • Algorithms
  • Alkylation
  • Antibiotics, Antineoplastic
  • Catalysis
  • DNA
  • Indoles
  • Kinetics
  • Leucomycins
  • Magnetic Resonance Spectroscopy
  • Phosphates
  • Pyrroles
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Identity

International Standard Serial Number (ISSN)

  • 0960-894X

Digital Object Identifier (DOI)

  • 10.1016/s0960-894x(01)00740-5

PubMed ID

  • 11814783
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Additional Document Info

start page

  • 303

end page

  • 306

volume

  • 12

issue

  • 3

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