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Mechanism of action of adenosylcobalamin. 3-Fluoro-1,2-propanediol as substrate for propanediol dehydrase. Mechanistic implications

Eagar, Robert G., Jr. and Bachovchin, William W. and Richards, John H. (1975) Mechanism of action of adenosylcobalamin. 3-Fluoro-1,2-propanediol as substrate for propanediol dehydrase. Mechanistic implications. Biochemistry, 14 (25). pp. 5523-5528. ISSN 0006-2960. http://resolver.caltech.edu/CaltechAUTHORS:20150505-134541144

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Abstract

3-Fluoro-1,2-propanediol has been found to be a substrate for propanediol dehydrase and has very similar binding and catalytic constants compared to the natural substrate. The only isolable products of the reaction are acrolein and inorganic fluoride; with 3-fluoro-3,3-dideuterio-l,2-propanediol as substrate, only 3,3-dideuterioacrolein is obtained. These results indicate that the primary product of the reaction is 3-fluoropropionaldehyde which spontaneously loses hydrogen fluoride to yield acrolein. The similar kinetic parameters for the fluorinated as compared to the normal substrate suggest that significant charge does not develop on the fluorinated or, by implication, the natural substrate during any rate-limiting steps of the reaction. These results support a radical, as contrasted to an ionic pathway for reactions involving adenosylcobalamin and diol dehydrase.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/bi00696a022DOIArticle
http://pubs.acs.org/doi/abs/10.1021/bi00696a022PublisherArticle
Additional Information:© 1975 American Chemical Society. Received July 10, 1975. This research was supported by National Institutes of Health Grant GM-10218.
Funders:
Funding AgencyGrant Number
NIHGM-10218
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Caltech Church Laboratory of Chemistry and Chemical Engineering5136
Record Number:CaltechAUTHORS:20150505-134541144
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20150505-134541144
Official Citation:Mechanism of action of adenosylcobalamin. 3-Fluoro-1,2-propanediol as substrate for propanediol dehydrase. Mechanistic implications Robert G. Eagar Jr., William W. Bachovchin, and John H. Richards Biochemistry 1975 14 (25), 5523-5528 DOI: 10.1021/bi00696a022
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:57239
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:06 May 2015 16:38
Last Modified:06 May 2015 16:38

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