Journal
CHEMCATCHEM
Volume 6, Issue 4, Pages 969-972Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201300904
Keywords
asymmetric synthesis; biocatalysis; carboligation; cross-coupling; thiamine-dependent enzymes
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Funding
- German Research Foundation (DFG) [FOR 1296]
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Thiamine diphosphate (ThDP) dependent enzymes catalyze the formation of acetoin (3-hydroxybutan-2-one) through one of three different pathways: homocoupling of pyruvate, homocoupling of acetaldehyde, or cross-coupling of acetaldehyde (as acceptor) and pyruvate (as donor). The enantioselectivity of the resulting acetoin is highly dependent on the particular enzyme. We established that ThDP-dependent cyclohexane-1,2-dione hydrolase (CDH) is able to form (S)-acetoin with particularly high enantioselectivity (up to 95%ee) by all three pathways. Mechanistic studies utilizing C-13-labeled substrates revealed an unprecedented non-acetolactate pathway for the homocoupling of pyruvate, which explains the high enantioselectivity in the CDH-catalyzed formation of (S)-acetoin.
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