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Enzymatic Hydrolysis of Tertiary Amide Bonds by anti Nucleophilic Attack and Protonation
KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Fiber- och polymerteknologi, Ytbehandlingsteknik. KTH, Skolan för kemi, bioteknologi och hälsa (CBH), Proteinvetenskap, Proteinteknologi. KTH, Centra, Science for Life Laboratory, SciLifeLab.ORCID-id: 0000-0002-4066-2776
2018 (engelsk)Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 83, nr 21, s. 13543-13548Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
American Chemical Society (ACS), 2018. Vol. 83, nr 21, s. 13543-13548
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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
Forskningsfinansiär
Swedish Research Council Formas, 2017-01116 2017-01116
Merknad

QC 20181127

Tilgjengelig fra: 2018-11-27 Laget: 2018-11-27 Sist oppdatert: 2019-08-20bibliografisk kontrollert

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