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. Author manuscript; available in PMC: 2010 May 1.
Published in final edited form as: Nat Chem. 2009 Nov 1;1(8):630–634. doi: 10.1038/nchem.410

Figure 1. π-Methyl-histidine-containing peptides for group transfer chemistry.

Figure 1

Previous work from the Miller group has resulted in selective transfer of acyl, phosphoryl, sulfinyl, and thiocarbonyl groups to alcohols using π-methyl-histidine-containing peptides. These reactions are thought to proceed through a N-methyl imidazolium intermediate generated by nucleophilic attack of the imidazole moiety on the electrophile. Careful design and optimization of the peptide catalysts can allow for the facile synthesis of a variety of analogs of complex polyols.