When the hydration of fumarate is catalyzed by the enzyme fumarase in D 2 O, only (2S,3R)-3-deuteriomalate

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When the hydration of fumarate is catalyzed by the enzyme fumarase in D2O, only (2S,3R)-3-deuteriomalate is formed as the product. (Each—CO–2 group is the conjugate base of a carboxylic acid group.)H H CO fumarate + D0 CO T 2 CH OD T 3 CH-D T CO 3-deuteriomalate fumarase (the 2S,3R stereoisomer is formed

This reaction can also be run in reverse. By applying the principle of microscopic reversibility, predict the product (if any) when each of the following compounds is treated with fumarase in H2O:(a) (c) -0C- M -0C- HO D H H *** **** H OH ***** CO HD CO (b) -0C- ******* HO H ******* DH CO

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Organic Chemistry

ISBN: 9781936221349

6th Edition

Authors: Marc Loudon, Jim Parise

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