Stereochemistry in enzyme inhibition: synthesis and evaluation of enantiomerically pure 2-benzyl-3-formylpropanoic acids as inhibitors of carboxypeptidase A

doi:10.1016/S0957-4166(99)00421-8

Paper

Stereochemistry in enzyme inhibition: synthesis and evaluation of enantiomerically pure 2-benzyl-3-formylpropanoic acids as inhibitors of carboxypeptidase A

Published Sep 24, 1999 · D. H. Kim, Suhman Chung

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Abstract

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Study Snapshot

The (R)-form of 2-benzyl-3-formylpropanoic acid is 674-fold more potent than its enantiomer as an inhibitor of carboxypeptidase A, suggesting it is a transition state analog inhibitor.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Stereochemistry in enzyme inhibition: synthesis and evaluation of enantiomerically pure 2-benzyl-3-formylpropanoic acids as inhibitors of carboxypeptidase A

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References

Inhibition of carboxypeptidase A by aldehyde and ketone substrate analogues.

Hydrable aldehyde DL-2-benzyl-3- formylpropanoic acid mimics the transition state for amide hydrolysis, while nonhydratable ketone does not.

Nature of Forces between Large Molecules of Biological Interest

The study of forces between large molecules of biological interest is crucial for understanding the structure and function of living organisms.

Citations

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The structural requirements of histone deacetylase inhibitors: C4-modified SAHA analogs display dual HDAC6/HDAC8 selectivity.

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Synthesis and Evaluation of Optical 2‐Benzyl‐5‐bromo‐4‐oxopentanoic Acids as Transition‐state Analog Inhibitors against Carboxypeptidase A

The (R)-form of 2-benzyl-5-bromo-4-oxopentanoic acid is 260-fold more potent than the (S)-form, with the gem-diol form potentially chelating the zinc ion in the active site of carboxypeptidas