Jump to main content
Jump to site search


Synthesis and glycosidase inhibition of N-substituted derivatives of DIM

Abstract

N-Substituted derivatives of DIM (1,4-dideoxy-1,4-imino-D-mannitol), the pyrrolidine core of swainsonine, have been synthesized efficiently and stereoselectively from D-mannose with 2,3:5,6-di-O-isopropylidene DIM (10) as key intermediate. These N-substituted derivatives include N-alkylated, N-alkenylated, N-hydroxyalkylated and N-aralkylated DIMs with the carbon number of the alkyl chain ranging from one to nine. The obtained 33 N-substituted DIM derivatives were assayed against various glycosidases, which allowed a systematic evaluation of their glycosidase inhibition profiles. Though N-substitution of DIM decreased their α-mannosidase inhibitory activities, some of the derivatives showed significiant inhibiton of other glycosidases.

Back to tab navigation

Supplementary files

Publication details

The article was received on 18 Sep 2019, accepted on 20 Nov 2019 and first published on 21 Nov 2019


Article type: Paper
DOI: 10.1039/C9OB02029B
Org. Biomol. Chem., 2019, Accepted Manuscript

  •   Request permissions

    Synthesis and glycosidase inhibition of N-substituted derivatives of DIM

    L. Yang, Y. Shimadate, A. Kato, Y. Li, Y. Jia, G. W.J. Fleet and C. Yu, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9OB02029B

Search articles by author

Spotlight

Advertisements