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Enzymatic Hydrolysis of Tertiary Amide Bonds by anti Nucleophilic Attack and Protonation
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology. KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Protein Science, Protein Technology. KTH, Centres, Science for Life Laboratory, SciLifeLab.ORCID iD: 0000-0002-4066-2776
2018 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 83, no 21, p. 13543-13548Article in journal (Refereed) Published
Abstract [en]

The molecular mechanisms conferring high resistance of planar tertiary amide bonds to hydrolysis by most enzymes have remained elusive. To provide a chemical explanation to this unresolved puzzle, UB3LYP calculations were performed on an active site model of Xaa-Pro peptidases. The calculated reaction mechanism demonstrates that biocatalysts capable of tertiary amide bond hydrolysis capitalize on anti nucleophilic attack and protonation of the amide nitrogen, in contrast to the traditional syn displayed by amidases and proteases acting on secondary amide bonds.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2018. Vol. 83, no 21, p. 13543-13548
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-239484DOI: 10.1021/acs.joc.8b02053ISI: 000449443200058PubMedID: 30256635Scopus ID: 2-s2.0-85054958555OAI: oai:DiVA.org:kth-239484DiVA, id: diva2:1266159
Funder
Swedish Research Council Formas, 2017-01116 2017-01116
Note

QC 20181127

Available from: 2018-11-27 Created: 2018-11-27 Last updated: 2019-08-20Bibliographically approved

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Syrén, Per-Olof

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