Stereoselective synthesis of vicinal diols with enzymatic cascade reactions
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Beschreibung
Alcohol dehydrogenases are of high interest for the stereoselective synthesis of
building blocks with multi-chiral centres. They are implemented for single
enzymatic reduction or oxidation steps or be part of synthetic enzymatic multi-step
cascades for the production of industrially relevant chiral synthons.
Although biotransformations with alcohol dehydrogenases are widespread,
enzymes, which accept sterically demanding substrates, especially α-hydroxy
ketones, are not common in nature. Therefore chemical methods for the synthesis
of chiral 1,2-diols are still first choice.
As a drawback, alcohol dehydrogenases require expensive nicotinamide cofactors
such as NAD(H) or NADP(H) for their activity. Prices of these cofactors prevent
their application in stoichiometric amounts and therefore regeneration of
nicotinamide cofactors is an essential issue for biotechnological purposes. Therefore
a co-substrate is required that is transformed to the respective co-product in
equimolar amounts relative to the product. This co-product has to be separated
from the product or must be removed in situ, which decreases atom- and process
economy.
In this work the carboligation of two inexpensive aldehydes catalysed by ThDPdependent
enzymes is combined with a subsequent reduction of the intermediately
formed α-hydroxy ketone by alcohol dehydrogenases. Therefore, a suitable cofactor
regeneration system with smart in situ co-product removal had to be developed in
order to gain high eco-efficiency of the synthetic enzyme cascade. To achieve the
aim, the following work packages were addressed: ...
Autor*in
Justyna Katarzyna Kulig
Themen in »Stereoselective synthesis of vicinal diols with enzymatic cascade reactions«
Green Chemistry NAD(H) NADP(H)