title: Syntheses and reactivities of non-symmetrical "active ester" bi-dentate cross-linking reagents having a phthalimidoyl and acid chloride, 2-benzothiazole, or 1-benzotriazole group.
abstract: We have newly synthesized the non-symmetrical "phthalimidoyl active ester" bi-dentate cross-linking reagents having an acid chloride, 2-benzothiazole, or 1-benzotriazole group (i.e., 9, 15, and 16) on the basis of the reactivity study of the "active ester" model compounds, 11-14, toward the various nucleophiles and examined their reaction selectivity towards the same nucleophiles. Then, we applied for the modification of cholesterol at the more reactive site of the bi-dentate linkers to give 3β-cholesteryl 4-(phthalimidoyloxycarbonyl)butyrate (39), and the subsequent reaction of 39 with several amines, such as benzylamine, 4-chlorobenzylamine, 2-phenylethylamine, L-phenylalanine methyl ester, or diphenylalanine benzyl ester as a protein model of the cholesterol antigen.
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan. chansheikh@yahoo.com
authors.forename: Md Chanmiya
authors.initials: MC
authors.lastname: Sheikh
authors.forename: Shunsuke
authors.initials: S
authors.lastname: Takagi
authors.forename: Mebumi
authors.initials: M
authors.lastname: Sakai
authors.forename: Tasuya
authors.initials: T
authors.lastname: Mori
authors.forename: Naoto
authors.initials: N
authors.lastname: Hayashi
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Fujie
authors.forename: Shin
authors.initials: S
authors.lastname: Ono
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Yoshimura
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Morita
mesh_terms: D000143:Acids / Q000737:chemistry*; D052160:Benzothiazoles / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000143:Acids; D052160:Benzothiazoles; D002712:Chlorides; D003432:Cross-Linking Reagents; D004952:Esters; C005465:benzothiazole