AUTHOR=Zhou Yixuan , Liao Kuo-Shiang , Li Shiou-Ting , Wu Chung-Yi 

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

JOURNAL=Frontiers in Chemistry

VOLUME=10

YEAR=2022

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2022.865026

DOI=10.3389/fchem.2022.865026

ISSN=2296-2646

ABSTRACT=<p>We presented a facile and scalable route for the synthesis of di-azido sugars <italic>via</italic> one-pot double inversion of the mono-benzoyl sugars by TBAN<sub>3</sub> 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.</p>