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Issue 2, 2017
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One-pot, two-step cascade synthesis of naturally rare l-erythro (3S,4S) ketoses by coupling a thermostable transaminase and transketolase

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Abstract

An efficient simultaneous cascade of two enzymatic steps catalyzed by a thermostable transaminase and transketolase was performed at elevated temperatures allowing the synthesis of naturally rare L-erythro (3S,4S) ketoses. L-ribulose, 5-deoxy-L-ribulose, D-tagatose and L-psicose, which are highly valuable chiral building blocks and display prominent biological properties, were obtained on a preparative scale with excellent stereoselectivities and good yields. A thermostable transketolase from Geobacillus stearothermophilus catalyzed at high temperatures the stereospecific synthesis of L-erythro (3S,4S)-configured ketoses from (2S)-hydroxylated aldehydes and β-hydroxypyruvate in which the latter is generated in an unprecedented manner in situ from natural L-serine and pyruvate using a novel thermostable L-α-transaminase from the thermophilic bacterium Thermosinus carboxydivorans. Overall, this cascade synthesis prevents the thermal decomposition of the labile β-hydroxypyruvate and offers an efficient and environmentally friendly procedure.

Graphical abstract: One-pot, two-step cascade synthesis of naturally rare l-erythro (3S,4S) ketoses by coupling a thermostable transaminase and transketolase

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Article information


Submitted
22 Jul 2016
Accepted
07 Sep 2016
First published
07 Sep 2016

Green Chem., 2017,19, 425-435
Article type
Paper

One-pot, two-step cascade synthesis of naturally rare L-erythro (3S,4S) ketoses by coupling a thermostable transaminase and transketolase

M. Lorillière, M. De Sousa, F. Bruna, E. Heuson, T. Gefflaut, V. de Berardinis, T. Saravanan, D. Yi, W. Fessner, F. Charmantray and L. Hecquet, Green Chem., 2017, 19, 425
DOI: 10.1039/C6GC02015A

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