Reductive Amination of Glycosyl Aldoses: Synthesis of N‐Glycosylated β‐Glycosyl Amino Alcohols and their Enzyme Inhibitory Effect

Abstract

Reductive amination of glycosyl aldehydes (1a–c, 2) with glycosyl amino esters (3a–c, 4) in the presence of sodium borohydride gave diglycosylated amino esters (5–15) in good yield. N‐Glycosyl‐glycosylated amino esters were reduced to the respective diglycosyl amino alcohols (16–26) with LiAlH₄ in good yield. All the synthesized compounds were studied for their inhibitory effect, if any, against hepatic glucose‐6‐phosphatase, glycogen phosphorylase, and intestinal brush border membrane α‐glucosidase; among these compounds 7, 21, and 25 have shown marked inhibition on these enzymes, respectively.

^#CDRI Communication No. 6605.

Acknowledgments

Authors are thankful to the Director of CDRI for his encouragement and to the Heads of microbiology and new target discovery and development divisions for antimicrobial screening. Financial assistance from ICMR New Delhi in the form of a Project BMS‐II 58/6/2000 is also acknowledged.

Notes

^#CDRI Communication No. 6605.