1240249-80-2Relevant academic research and scientific papers
Synthesis of allose-templated hydroxyornithine and hydroxyarginine analogs
Mondal, Dhananjoy,Schweizer, Frank
experimental part, p. 1533 - 1540 (2010/08/20)
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.
