title: Synthesis of allose-templated hydroxyornithine and hydroxyarginine analogs.
abstract: Conformationally constrained amino acid analogs are widely used to probe the bioactive conformation of peptides. In this paper we report on the synthesis of hexafunctional allose-templated L- and D-hydroxyornithine and L- and D-hydroxyarginine analogs in which the allose-based polyol scaffold constrains the side chain of hydroxyornithine and hydroxyarginine in an extended conformation. The partially protected building blocks were selected for future use in solid-phase peptide synthesis using the Fmoc-strategy. The synthesis starts from a previously prepared C-glucosyl glycine analog. Multiple chemical protection-deprotection steps and an oxidation are used to prepare 3-keto-C-glucosyl analogs that serve as a precursor to install an amino function via reductive amination. Guanidinylation of the amino group provides access to allose-templated hydroxyarginine analogs. Both hexafunctional building blocks are further chemically modified to provide suitable protection for solid-phase peptide synthesis using the Fmoc-strategy.
authors.affiliation: Department of Chemistry, University of Manitoba, Winnipeg, Manitoba, Canada.
authors.forename: Dhananjoy
authors.initials: D
authors.lastname: Mondal
authors.forename: Frank
authors.initials: F
authors.lastname: Schweizer
mesh_terms: D001120:Arginine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D005947:Glucose / Q000737:chemistry*; D008968:Molecular Conformation; D009952:Ornithine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D010455:Peptides; C012356:gamma-hydroxyarginine; C002055:allose; D001120:Arginine; D009952:Ornithine; D005947:Glucose