Tanaka K, Inoue T, Tezuka Y, Kikuchi T
National Research Institute of Police Science, Tokyo, Japan.
Chem Pharm Bull (Tokyo). 1996 Feb;44(2):273-9. doi: 10.1248/cpb.44.273.
Reactions of illudin S with cysteine derivatives (cysteine methyl ester, glutathione and a peptide, Cys-Asp-Pro-Gly-Tyr-Ile-Gly-Ser-Arg) were investigated. In the reaction with cysteine methyl ester, four products (P1, P2, P3, P4) were obtained and their structures were determined, on the basis of MS and NMR data, to be adducts of the mercapto group of cysteine methyl ester with the alpha,beta-unsaturated carbonyl group of illudin S. In the reactions with glutathione and the peptide, two addition products in each case were identified by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and NMR analyses. The structures of these adducts also indicated that the alpha,beta-unsaturated carbonyl group in illudin S behaves as a Michael acceptor for the mercapto group in cysteine.
研究了隐杯伞素S与半胱氨酸衍生物（半胱氨酸甲酯、谷胱甘肽和一种肽，Cys-Asp-Pro-Gly-Tyr-Ile-Gly-Ser-Arg）的反应。在与半胱氨酸甲酯的反应中，得到了四种产物（P1、P2、P3、P4），并根据质谱和核磁共振数据确定了它们的结构，即半胱氨酸甲酯的巯基与隐杯伞素S的α,β-不饱和羰基的加合物。在与谷胱甘肽和该肽的反应中，通过液相色谱-串联质谱（LC-MS/MS）和核磁共振分析分别鉴定出两种加成产物。这些加合物的结构还表明，隐杯伞素S中的α,β-不饱和羰基作为半胱氨酸中巯基的迈克尔受体。
