When the hydration of fumarate is catalyzed by the enzyme fumarase in D 2 O, only (2S,3R)-3-deuteriomalate
Question:
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.)
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:
Transcribed Image Text:
H H CO₂ fumarate + D₂0 CO₂ T 2 CH OD T 3 CH-D T CO₂ 3-deuteriomalate fumarase (the 2S,3R stereoisomer is formed exclusively)
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First draw the 2S3R stereoisomer of the product so that the stereochemistry of the addition can be deduced Only a malate stereoisomer with the 2S conf...View the full answer
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