Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 21, Pages 5005-5009Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201701020
Keywords
aldolization; biocatalysis; enzymes; fructose-6-phosphate aldolase; phosphorylated compounds
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Funding
- Auvergne council
- Bundesministerium fur Bildung und Forschung (BMBF) [0315775B PT-J]
- Ministerio de Economia y Competitividad (MINECO) [CTQ2015-63563-R, CTQ2015-64436-P]
- COST action Systems Bio-catalysis [CM1303]
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d-Fructose-6-phosphate aldolase (FSA) was probed for extended nucleophile promiscuity by using a series of fluorogenic substrates to reveal retro-aldol activity. Four nucleophiles ethanal, propanone, butanone, and cyclopentanone were subsequently confirmed to be non-natural substrates in the synthesis direction using the wild-type enzyme and its D6H variant. This exceptional widening of the nucleophile substrate scope offers a rapid entry, in good yields and high stereoselectivity, to less oxygenated alkyl ketones and aldehydes, which was hitherto impossible.
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