Reversed and Sandwiched Analogs of Duocarmycin SA: Establishment of the Origin of the Sequence-Selective Alkylation of DNA and New Insights into the Source of Catalysis
- 1 May 1997
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 119 (21) , 4987-4998
- https://doi.org/10.1021/ja9637210
Abstract
No abstract availableKeywords
This publication has 21 references indexed in Scilit:
- Total Synthesis of (+)-Duocarmycin A, epi-(+)-Duocarmycin A and Their Unnatural Enantiomers: Assessment of Chemical and Biological PropertiesJournal of the American Chemical Society, 1997
- Acid-Dependent Electrophilicity of Cyclopropylpyrroloindoles. Nature's Masking Strategy for a Potent DNA AlkylatorJournal of the American Chemical Society, 1994
- (+)- and ent-(-)-Duocarmycin SA and (+)- and ent-(-)-N-BOC-DSA DNA Alkylation Properties.Alkylation Site Models That Accommodate the Offset AT-Rich Adenine N3 Alkylation Selectivity of the Enantiomeric AgentsJournal of the American Chemical Society, 1994
- Structure of the (+)-CC-1065-DNA adduct: critical role of ordered water molecules and implications for involvement of phosphate catalysis in the covalent reactionBiochemistry, 1991
- (+)-CC-1065 produces bending of DNA that appears to resemble adenine/thymine tractsChemical Research in Toxicology, 1991
- A demonstration of the intrinsic importance of stabilizing hydrophobic binding and non-convalent van der waals contacts dominant in the non-covalent CC-1065/B-DNA bindingChemico-Biological Interactions, 1990
- Synthesis and preliminary evaluation of agents incorporating the pharmacophore of the duocarmycin/pyrindamycin alkylation subunit: identification of the CC-1065/duocarmycin common pharmacophoreThe Journal of Organic Chemistry, 1990
- The electrostatic potential of B‐DNABiopolymers, 1989
- Sequence selectivity of DNA covalent modificationChemical Research in Toxicology, 1988
- Total synthesis of (.+-.)-N2-(phenylsulfonyl)-CPI, (.+-.)-CC-1065, (+)-CC-1065, ent-(-)-CC-1065, and the precise, functional agents (.+-.)-CPI-CDPI2, (+)-CPI-CDPI2, and (-)-CPI-CDPI2 [(.+-.)-(3bR*,4aS*)-, (+)-(3bR,4aS)-, and (-)-(3bS,4aR)-deoxy-CC-1065]Journal of the American Chemical Society, 1988