AI Article Synopsis
- Thiamine diphosphate (ThDP) dependent enzymes catalyze asymmetric C-C bond formation through benzoin-type reactions, primarily producing α-hydroxy ketones.
- A wide variety of aldehydes and ketones can be used as acceptor substrates, but the usual donor substrates are mainly limited to simple, achiral molecules.
- A study identified a new subclass of ThDP-dependent enzymes that can use functionalized chiral α-keto acids as donors, greatly expanding the substrate range and allowing for high-yield production of enantioenriched compounds.
Article Abstract
Thiamine diphosphate (ThDP) dependent enzymes are useful catalysts for asymmetric C-C bond formation through benzoin-type condensation reactions that result in α-hydroxy ketones. A wide range of aldehydes and ketones can be used as acceptor substrates; however, the donor substrate range is mostly limited to achiral α-keto acids and simple aldehydes. By using a unifying retro-biosynthetic approach towards acyl-branched sugars, we identified a subclass of (myco)bacterial ThDP-dependent enzymes with a greatly extended donor substrate range, namely functionalized chiral α-keto acids with a chain length from C to C . Highly enantioenriched acyloin products were obtained in good to high yields and several reactions were performed on a preparative scale. The newly introduced functionalized α-keto acids, accessible by known aldolase-catalyzed transformations, substantially broaden the donor substrate range of ThDP-dependent enzymes, thus enabling a more general use of these already valuable catalysts.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9306805 | PMC |
| http://dx.doi.org/10.1002/anie.202113405 | DOI Listing |
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