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Mechanism of action of adenosylcobalamin: hydrogen transfer in the inactivation of diol dehydratase by glycerol

Bachovchin, William W. and Moore, Kevin W. and Richards, John H. (1978) Mechanism of action of adenosylcobalamin: hydrogen transfer in the inactivation of diol dehydratase by glycerol. Biochemistry, 17 (11). pp. 2218-2224. ISSN 0006-2960. https://resolver.caltech.edu/CaltechAUTHORS:20150501-152518245

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Abstract

We have investigated the kinetic characteristics of the inactivation of the adenosylcobalamin-dependent enzyme propanediol dehydratase by glycerol, (RS)-1,1-dideuterioglycerol, (R)-1,1-dideuterioglycerol, and perdeuterioglycerol in the presence of 1,2-propanediol and 1,1-dideuterio- 1,2-propanediol. The results imply that hydrogen (or deuterium) attached to C-1 of 1,2-propanediol participates in the inactivation process and contributes to the expression of a kinetic isotope effect on the rate of inactivation. The mechanism for this inactivation must involve the cofactor as an intermediate hydrogen carrier, presumably in the form of 5’-deoxyadenosine. Moreover, a mechanism involving a rate-determining transfer of hydrogen from an intermediate containing three equivalent hydrogens quantitatively accounts for all of the results. When diol dehydratase holoenzyme is inactivated by [ 1^(-3)H glycerol, 5’-deoxyadenosine which is enriched in tritium by a factor of 2.1 over that in glycerol can be isolated from the reaction mixture.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/bi00604a031DOIArticle
http://pubs.acs.org/doi/abs/10.1021/bi00604a031PublisherArticle
Additional Information:© 1978 American Chemical Society. Received September 13 1977. Contribution No. 5657 from the Church Laboratory of Chemical Biology, Division of Chemistry and Chemical Engineering, California Institute of Technology. Pasadena, California 91 125. Received September 13, 1977. This research was supported by National Institutes of Health Grant GM-10218. National Institutes of Health Trainee (GM 01262).
Funders:
Funding AgencyGrant Number
NIHGM-10218
NIHGM-01262
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Other Numbering System NameOther Numbering System ID
Caltech Division of Chemistry and Chemical Engineering5657
Issue or Number:11
Record Number:CaltechAUTHORS:20150501-152518245
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20150501-152518245
Official Citation:Bachovchin, W. W., Moore, K. W., & Richards, J. H. (1978). Mechanism of action of adenosylcobalamin: hydrogen transfer in the inactivation of diol dehydratase by glycerol. Biochemistry, 17(11), 2218-2224. doi: 10.1021/bi00604a031
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:57168
Collection:CaltechAUTHORS
Deposited By: Joanne McCole
Deposited On:01 May 2015 23:34
Last Modified:03 Oct 2019 08:21

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