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
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)|
|Degree Grantor:||California Institute of Technology|
|Division:||Chemistry and Chemical Engineering|
|Thesis Availability:||Public (worldwide access)|
|Defense Date:||27 May 1976|
|Default Usage Policy:||No commercial reproduction, distribution, display or performance rights in this work are provided.|
|Deposited By:||Tony Diaz|
|Deposited On:||19 Apr 2010 16:54|
|Last Modified:||26 Dec 2012 03:24|
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