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MacDonald MJ, Lavis LD, Hilvert D, et al. Evaluation of the Ser-His Dipeptide, a Putative Catalyst of Amide and Ester Hydrolysis. Org Lett. 2016;18(15):3518-21doi: 10.1021/acs.orglett.6b01279.
MacDonald, M. J., Lavis, L. D., Hilvert, D., & Gellman, S. H. (2016). Evaluation of the Ser-His Dipeptide, a Putative Catalyst of Amide and Ester Hydrolysis. Organic letters, 18(15), 3518-21. https://doi.org/10.1021/acs.orglett.6b01279
MacDonald, Melissa J, et al. "Evaluation of the Ser-His Dipeptide, a Putative Catalyst of Amide and Ester Hydrolysis." Organic letters vol. 18,15 (2016): 3518-21. doi: https://doi.org/10.1021/acs.orglett.6b01279
MacDonald MJ, Lavis LD, Hilvert D, Gellman SH. Evaluation of the Ser-His Dipeptide, a Putative Catalyst of Amide and Ester Hydrolysis. Org Lett. 2016 Aug 05;18(15):3518-21. doi: 10.1021/acs.orglett.6b01279. Epub 2016 Jul 11. PMID: 27400366.
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Org Lett. 2016 Aug 05;18(15):3518-21. doi: 10.1021/acs.orglett.6b01279. Epub 2016 Jul 11.

Evaluation of the Ser-His Dipeptide, a Putative Catalyst of Amide and Ester Hydrolysis.

Organic letters

Melissa J MacDonald, Luke D Lavis, Donald Hilvert, Samuel H Gellman

Affiliations

  1. Department of Chemistry, University of Wisconsin-Madison , Wisconsin 53706, United States.
  2. Janelia Research Campus, Howard Hughes Medical Institute , Ashburn, Virginia 20147, United States.
  3. Laboratory of Organic Chemistry, ETH Zürich , 8093 Zürich, Switzerland.

PMID: 27400366 DOI: 10.1021/acs.orglett.6b01279

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.

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