Action of Molybdate Anion on d-Glucosone: Catalytic Conversion to Aldonates Involving C1-C2 Transposition.

ABSTRACT: Treatment of the osone (aldos-2-ulose), d-[1-¹³C]glucosone (1 ¹), with sodium molybdate at 90° for 30 h gave a mixture of d-[2-¹³C]gluconate (2 ²) and d-[2-¹³C]mannonate (3 ²) in an 85:15 ratio, indicating that the reaction proceeds with C1-C2 transposition similar to that observed previously with aldoses. Reactions with several singly and doubly ¹³C-labeled isotopomers of 1 confirmed this transposition. In contrast to the aldose reaction, the reaction with 1 is irreversible, presumably due to electrostatic repulsion between the negatively charged catalytically active bimolybdate species and the negatively charged aldonate product. The production of 2 and 3 is media

SUBMITTER: Zhang W 

PROVIDER: S-EPMC11447727 | biostudies-literature | 2024 Oct

REPOSITORIES: biostudies-literature