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Science 28 July 1995:
Vol. 269. no. 5223, pp. 527 - 529
DOI: 10.1126/science.7624773
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Articles

Science, Vol 269, Issue 5223, 527-529
Copyright © 1995 by American Association for the Advancement of Science

articles

Importance of historical contingency in the stereochemistry of hydratase-dehydratase enzymes

Mohrig JR, KA Moerke, DL Cloutier, BD Lane, EC Person, and TB Onasch

Department of Chemistry, Carleton College, Northfield, MN 55057, USA.

There are two stereochemical classes of hydratase-dehydratase enzymes. Those that catalyze the addition of water to alpha, beta-unsaturated thioesters give syn addition-elimination stereochemistry, whereas those that catalyze the addition of water to conjugated carboxylate substrates give anti stereochemistry. This dichotomy could reflect different adaptive advantages or contingencies of separate evolutionary histories. Determination of the nonenzymatic stereochemistry of deuterium oxide addition to fumarate and to S-crotonyl N-acetylcysteamine has provided direct evidence for the importance of the contingencies of evolutionary history, rather than chemical efficiency, in the pathways of these hydratase-dehydratase enzymes.


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