Transketolase and fructose-1,6-bis-phosphate aldolase, complementary tools for access to new ulosonic acid analogues

A new approach to the synthesis of ulosonic acids KDO and DAH is described. The key step is the C₅-C₆ bond formation catalysed by fructose-1,6-bisphosphate aldolase (for KDO) or transketolase (for DAH) using substituted acrylonitrile α-hydroxyaldehyde. All asymmetric carbon configurations are determined in an enzymatic step by the means of deshydrogenase or lipase. This strategy, using a non-metabolism pathway, allows access to novel precursors of KDO, DAH and analogues.