title: One-pot protection-glycosylation reactions for synthesis of lipid II analogues.
abstract: (2,6-Dichloro-4-methoxyphenyl)(2,4-dichlorophenyl)methyl trichloroacetimidate (3) and its polymer-supported reagent 4 can be successfully applied to a one-pot protection-glycosylation reaction to form the disaccharide derivative 7 d for the synthesis of lipid II analogues. The temporary protecting group or linker at the C-6 position and N-Troc protecting group of 7 d can be cleaved simultaneously through a reductive condition. Overall yields of syntheses of lipid II (1) and neryl-lipid II N(ε)-dansylthiourea are significantly improved by using the described methods.
authors.affiliation: Department of Pharmaceutical Sciences, College of Pharmacy, University of Tennessee Health Science Center, 881 Madison Avenue, Memphis, TN 38163-0001 (USA), Fax: (+1) 901-448-6940.
authors.forename: Katsuhiko
authors.initials: K
authors.lastname: Mitachi
authors.forename: Priya
authors.initials: P
authors.lastname: Mohan
authors.forename: Shajila
authors.initials: S
authors.lastname: Siricilla
authors.forename: Michio
authors.initials: M
authors.lastname: Kurosu
mesh_terms: D000081:Acetamides / Q000737:chemistry; D062845:Chloroacetates / Q000737:chemistry; D004187:Disaccharides / Q000737:chemistry; D006031:Glycosylation; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis* / Q000737:chemistry; D008738:Methyl Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D046928:Peptidoglycan Glycosyltransferase / Q000737:chemistry / Q000378:metabolism; D011108:Polymers / Q000737:chemistry; D014538:Uridine Diphosphate N-Acetylmuramic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: C000596820:(2,6-dichloro-4-methoxyphenyl)(2,4-dichlorophenyl)methyl ether; D000081:Acetamides; D062845:Chloroacetates; D004187:Disaccharides; D006843:Hydrocarbons, Chlorinated; D008738:Methyl Ethers; D011108:Polymers; D014538:Uridine Diphosphate N-Acetylmuramic Acid; C069249:muramyl-NAc-(pentapeptide)pyrophosphoryl-undecaprenol; D046928:Peptidoglycan Glycosyltransferase; C009528:trichloroacetamide
keywords: biosynthesis; lipid II; one-pot synthesis; peptidoglycans; transglycosylase (TGase)