†Department of Chemistry and Biochemistry, University of California Los Angeles, Los Angeles, California 90095-1569, United States.
‡Department of Bioengineering, University of California Los Angeles, Los Angeles, California 90095-1600, United States.
Biomacromolecules. 2015 Jun 8;16(6):1802-6. doi: 10.1021/acs.biomac.5b00372. Epub 2015 May 26.
Methodology was developed for efficient alkylation of methionine residues using epoxides as a general strategy to introduce a wide range of functional groups onto polypeptides. Use of a spacer between epoxide and functional groups further allowed addition of sterically demanding functionalities. Contrary to other methods to alkylate methionine residues, epoxide alkylations allow the reactions to be conducted in wet protic media and give sulfonium products that are stable against dealkylation. These functionalizations are notable since they are chemoselective, utilize stable and readily available epoxides, and allow facile incorporation of an unprecedented range of functional groups onto simple polypeptides using stable linkages.
方法学是为了使用环氧化物作为一种通用策略，高效地对甲硫氨酸残基进行烷基化而开发的，以将广泛的官能团引入多肽中。在环氧化物和官能团之间使用间隔物进一步允许添加空间要求高的官能团。与其他用于烷基化甲硫氨酸残基的方法相反，环氧化物烷基化允许在湿润的质子介质中进行反应，并得到稳定的锍产物，不易发生脱烷基化。这些官能化是显著的，因为它们是化学选择性的，利用稳定且易于获得的环氧化物，并允许使用稳定的键，在简单的多肽上方便地引入前所未有的一系列官能团。
