title: Evaluation of the Ser-His Dipeptide, a Putative Catalyst of Amide and Ester Hydrolysis.
abstract: Efficient hydrolysis of amide bonds has long been a reaction of interest for organic chemists. The rate constants of proteases are unmatched by those of any synthetic catalyst. It has been proposed that a dipeptide containing serine and histidine is an effective catalyst of amide hydrolysis, based on an apparent ability to degrade a protein. The capacity of the Ser-His dipeptide to catalyze the hydrolysis of several discrete ester and amide substrates is investigated using previously described conditions. This dipeptide does not catalyze the hydrolysis of amide or unactivated ester groups in any of the substrates under the conditions evaluated.
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison , Wisconsin 53706, United States.
authors.forename: Melissa J
authors.initials: MJ
authors.lastname: MacDonald
authors.affiliation: Janelia Research Campus, Howard Hughes Medical Institute , Ashburn, Virginia 20147, United States.
authors.forename: Luke D
authors.initials: LD
authors.lastname: Lavis
authors.affiliation: Laboratory of Organic Chemistry, ETH Zürich , 8093 Zürich, Switzerland.
authors.forename: Donald
authors.initials: D
authors.lastname: Hilvert
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison , Wisconsin 53706, United States.
authors.forename: Samuel H
authors.initials: SH
authors.lastname: Gellman