Synthesis of C6-modified mannose 1-phosphates and evaluation of derived sugar nucleotides against GDP-mannose dehydrogenase

We present herein the design and chemoenzymatic synthesis of sugar nucleotide tools to probe a critical enzyme within alginate biosynthesis, GDP-mannose dehydrogenase (GMD). We first synthesise C6-modified glycosyl 1-phosphates, incorporating 6-amino, 6-chloro and 6-sulfhydryl groups, followed by their evaluation as substrates for enzymatic pyrophosphorylative coupling. The development of this methodology enables access to GDP 6-chloro-6-deoxy-ᴅ-mannose and its evaluation against GMD. Beilstein J. Org. Chem. 2022, 18, 1379–1384. doi:10.3762/bjoc.18.142
Source: Beilstein Journal of Organic Chemistry - Category: Chemistry Authors: Tags: alginate chemical probe enzymatic synthesis GDP-mannose dehydrogenase sugar nucleotide Letter Source Type: research