Sequence specificity of DNA alkylation by the unnatural enantiomer of CC-1065 and its synthetic analogs

…, MA Mitchell, NA Wicnienski, I Gebhard

Index: Hurley; Warpehoski; Lee; McGovren; Scahill; Kelly; Mitchell; Wicnienski; Gebhard; Johnson; Bradford Journal of the American Chemical Society, 1990 ,  vol. 112,  # 12  p. 4633 - 4649

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Citation Number: 116

Abstract

Abstract:(-)-CC-1065, the unnatural enantiomer of the potent and sequence-selective, DNA- reactive antibiotic,(+)-CC-1065, was prepared by synthesis and its malent reaction with DNA was studied and compared to that of the natural product. Although (-)-CC-1065 also formed covalent adducts in which the cyclopropyl carbon was bonded to the N3 atom of adenine, and the thermal strand breakage that it produced paralleled that seen for (+)-CC-1065, it ...