title: Synthesis and inhibitory activity of 8-substituted 2-deoxy-beta-KDO against CMP-KDO synthetase.
abstract: 3-Deoxy-D-manno-octulosonate cytidyltransferase (CMP-KDO synthetase) is involved in the biosynthesis of lipopolysaccharide (LPS) which is an essential component of the outer membrane of gram-negative bacteria. New CMP-KDO synthetase inhibitors, 8-substituted derivatives of 2-deoxy-beta-KDO (2) have been prepared. Compounds 8, 11, 15 and 16 in which the 8-hydroxyl group of 2 is replaced by guanidine, di(carbamoylethyl)amino, p-methoxy- or p-nitro-benzyloxycarbonylamino, respectively affect moderately the CMP-KDO synthetase activity.
authors.affiliation: Microbial Chemistry Research Center, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.
authors.forename: Hayamitsu
authors.initials: H
authors.lastname: Adachi
authors.forename: Ken-Ichiro
authors.initials: K
authors.lastname: Kondo
authors.forename: Fukiko
authors.initials: F
authors.lastname: Kojima
authors.forename: Yoji
authors.initials: Y
authors.lastname: Umezawa
authors.forename: Keiko
authors.initials: K
authors.lastname: Ishino
authors.forename: Kunimoto
authors.initials: K
authors.lastname: Hotta
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Nishimura
mesh_terms: D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004926:Escherichia coli / Q000201:enzymology; D008956:Models, Chemical; D015394:Molecular Structure; D009713:Nucleotidyltransferases / Q000037:antagonists & inhibitors*
chemical_list: D004187:Disaccharides; D009713:Nucleotidyltransferases; C028984:3-deoxy-manno-octulosonate cytidyltransferase