Stereoselective Anomeric Phosphorylation under Modified Mitsunobu Reaction Conditions.

ABSTRACT: Glycosyl phosphates are vital components of various biomolecules and serve as intermediates in the biosynthesis of substrates for glycosyltransferases such as nucleotide-activated sugars and dolichol-phosphate sugars. Their limited availability underscores the importance of stereoselective chemical synthesis of glycosyl phosphates with a defined anomeric configuration. A particular challenge lies in the generation of glycosyl phosphates with an anomeric configuration opposite to that of the starting lactol, as exemplified by l/d-glycero-β-d-manno-heptosyl phosphate-precursors in the synthesis of the pathogen-associated molecular pattern ADP-heptose, which triggers innate immune signaling through interaction with α-kinase-1 (ALPK1). The modification of the Mitsunobu reaction e

SUBMITTER: Monti A 

PROVIDER: S-EPMC12501929 | biostudies-literature | 2025 Oct

REPOSITORIES: biostudies-literature