Facile and Scalable Route to Access Rare Deoxy Amino Sugars for Nonulosonic Acid Aldolase Biosynthesis

We presented a facile and scalable route for the synthesis of di-azido sugars via one-pot double inversion of the mono-benzoyl sugars by TBAN(3) and studied the dependency pattern between solvent and protecting groups as well as the configuration of the neighboring and leaving groups. Moreover, we developed a chemical synthetic strategy for pseudaminic acid precursors (11 steps in 49%). Furthermore, we discussed the configuration of nonulosonic acid precursors for specificity of PseI and PmNanA enzymatic synthesis, permitting us to synthesize new nonulosonic acid derivatives for accessing Pse isomers.

Automated summary

This article presents a facile and scalable route for synthesizing di-azido sugars and explores the dependency pattern between solvent and protecting groups. It also introduces a chemical synthetic strategy for pseudaminic acid precursors and discusses the configuration of nonulosonic acid precursors.