Synthesis and biological evaluation of gem-diamine 1-N-iminosugars related to L-iduronic acid as inhibitors of heparan sulfate 2-O-sulfotransferase.
A variety of gem-diamine 1-N-iminosugars related to L-iduronic acid were synthesized and evaluated as inhibitors of heparan sulfate uronyl 2-O-sulfotransferase using an in vitro enzyme assay. Two iminosugars containing guanidino groups acted as potent in vitro inhibitors of the enzyme.
Brown
Jillian R
JR
Department of Cellular and Molecular Medicine, Glycobiology Research and Training Center, University of California-San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0687, USA.
Nishimura
Yoshio
Y
Esko
Jeffrey D
JD
D000818:Animals; D001665:Binding Sites; D003959:Diamines / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D007067:Iduronic Acid / Q000737:chemistry*; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000494:pharmacology; D008956:Models, Chemical; D015238:Sulfotransferases / Q000037:antagonists & inhibitors*
D003959:Diamines; D004791:Enzyme Inhibitors; D050111:Imino Sugars; D007067:Iduronic Acid; D015238:Sulfotransferases; C106358:heparan-sulfate 2-sulfotransferase