title: Synthesis of guanidino sugar conjugates as GlcβArg analogs.
abstract: The β-glucosyl linkage to the guanidine group of arginine (Arg) is found in amylogenin, a glycoprotein from sweet corn. Such a linkage is formed by a rare N-glycosylation of proteins. Synthesis of analogs of the unusual N-glycosidic linkage (GlcβArg) with an acetamido or triazole spacer between the glycosyl residue and the guanidine moiety was accomplished by the reaction of fully acetylated sugar unit containing a free amino group with bis-Boc-thiourea. Synthesis of N-glucosylarginine with an amido linker was also achieved during the present study. This methodology was also extended to the synthesis of cationic glucolipid.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, India, amrisriv9@gmail.com.
authors.forename: Amrita
authors.initials: A
authors.lastname: Srivastava
authors.forename: Duraikkannu
authors.initials: D
authors.lastname: Loganathan
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis; D001120:Arginine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002241:Carbohydrates / Q000138:chemical synthesis*; D005960:Glucosides / Q000138:chemical synthesis*; D019791:Guanidine / Q000138:chemical synthesis; D014230:Triazoles / Q000138:chemical synthesis
chemical_list: D000081:Acetamides; D002241:Carbohydrates; D005960:Glucosides; D014230:Triazoles; C097154:glucosylarginine; D001120:Arginine; D019791:Guanidine