Evaluation of the Ser-His dipeptide, a putative catalyst of amide and ester hydrolysis.

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Organic Letters. 2016 Jul 11;. doi: 10.1021/acs.orglett.6b01279

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Evaluation of the Ser-His dipeptide, a putative catalyst of amide and ester hydrolysis. Lavis Lab

MacDonald MJ, Lavis LD, Hilvert D, Gellman SH

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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.

PMID: 27400366 [PubMed - indexed for MEDLINE]

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Evaluation of the Ser-His dipeptide, a putative catalyst of amide and ester hydrolysis.

Abstract

PMID: 27400366 [PubMed - indexed for MEDLINE]

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