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Analogues of 1, 2-propanediol, inactivators of dioldehydrase I. Studies on the effect of 3-halo-1, 2-propanediols on the coenzyme B_(12) dependent dioldehydrase reaction II. Studies on the effect of an epoxide on dioldehydrase

Citation

Lamkin, Mark Stuart (1976) Analogues of 1, 2-propanediol, inactivators of dioldehydrase I. Studies on the effect of 3-halo-1, 2-propanediols on the coenzyme B_(12) dependent dioldehydrase reaction II. Studies on the effect of an epoxide on dioldehydrase. Master's thesis, California Institute of Technology. http://resolver.caltech.edu/CaltechTHESIS:04052010-084939879

Abstract

PART I: 3-Chloro-1, 2 -propanediol, 3 -bromo-1, 2-propanediol, and 3-iodo-1, 2-propanediol have been found to bind to dioldehydrase. Dissociation constants are approximately equal in each case. Binding occurs in a manner similar to that of the normal substrate, 1, 2-propanediol. All three compounds behave as competitive inhibitors while 3-chloro-1, 2-propanediol and 3-brom-1, 2-propanediol inactivate the holoenzyme as well. This inactivation process is irreversible and may involve the alkylation of sulfhydryl residues of dioldehydrase. Of the above compounds, only 3-chloro-1, 2-propanediol is converted to product; possibly β-chloropropionaldehyde is formed. PART II: 2, 3-Epoxypropanol (glycidol) has been found to bind to dioldehydrase. Its calculated dissociation constant is 8.8 X 10^(-4) M. It binds to dioldehydrase even though it has but one hydroxyl group. 2, 3-Epoxypropanol behaves as a competitive inhibitor. This compound also inactivates the holoenzyme. Unlike the compounds studied in Part I, it also inactivates the apoenzyme, although at a slower rate. Since epoxides are known to alkylate sulfhydryl groups, the above result suggests the presence of exposed sulfhydryl residues.

Item Type:Thesis (Master's thesis)
Subject Keywords:Chemistry
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Richards, John H.
Thesis Committee:
  • Unknown, Unknown
Defense Date:27 May 1976
Record Number:CaltechTHESIS:04052010-084939879
Persistent URL:http://resolver.caltech.edu/CaltechTHESIS:04052010-084939879
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:5688
Collection:CaltechTHESIS
Deposited By: Tony Diaz
Deposited On:19 Apr 2010 16:54
Last Modified:26 Dec 2012 03:24

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