Jump to main content
Jump to site search

Issue 4, 2006
Previous Article Next Article

Synthesis of bisubstrate analogues targeting α-1,3-fucosyltransferase and their activities

Author affiliations

Abstract

We designed two bisubstrate analogues targeting α-1,3-fucosyltransferases, based on the three dimensional structure of Lewis X, which is the product of a α-1,3-fucosyltransferase reaction. We selected guanosine-5′-diphospho-L-galactose as a donor mimic and 2-hydroxyethyl β-D-galactoside as an acceptor mimic, and tethered these two mimics with a methylene or ethylene linker. For the synthesis, the 6-position of L-galactose and the 6-position of D-galactose were first tethered via a methylene or ethylene linker. The L-galactose moiety was then converted to a GDP derivative. Both bisubstrate analogues were moderate inhibitors against α-1,3-fucosyltransferase V and VI. The fact that they were substrates of α-1,3-fucosyltransferase VI suggested that these compounds bound to the donor binding site, but not to the acceptor binding site.

Graphical abstract: Synthesis of bisubstrate analogues targeting α-1,3-fucosyltransferase and their activities

Back to tab navigation

Supplementary files

Publication details

The article was received on 30 Sep 2005, accepted on 22 Nov 2005 and first published on 16 Dec 2005


Article type: Paper
DOI: 10.1039/B513897C
Org. Biomol. Chem., 2006,4, 681-690

  •   Request permissions

    Synthesis of bisubstrate analogues targeting α-1,3-fucosyltransferase and their activities

    M. Izumi, S. Kaneko, H. Yuasa and H. Hashimoto, Org. Biomol. Chem., 2006, 4, 681
    DOI: 10.1039/B513897C

Search articles by author

Spotlight

Advertisements