MacMillan Karen S, Boger Dale L
Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
J Am Chem Soc. 2008 Dec 10;130(49):16521-3. doi: 10.1021/ja806593w.
A unique alternative to the -spirocyclization for activation of compounds containing the duocarmycin SA alkylation subunit was established involving indole NH deprotonation and subsequent cyclopropane formation. The structural characterization of an alternative spirocyclization product, and the establishment of its relative reactivity, intrinsic reaction regioselectivity, biological activity, and DNA alkylation properties (selectivity, rate, and efficiency) including the isolation, characterization, and quantitation of its adenine N3 adduct, are disclosed.
建立了一种独特的替代 -螺环化反应,用于激活含有多卡霉素SA烷基化亚基的化合物,该反应涉及吲哚NH去质子化及随后的环丙烷形成。本文公开了一种替代螺环化产物的结构表征,及其相对反应活性、内在反应区域选择性、生物活性和DNA烷基化性质(选择性、速率和效率),包括其腺嘌呤N3加合物的分离、表征和定量。