Synthesis of allose-templated hydroxyornithine and hydroxyarginine analogs.
作者： Dhananjoy Mondal , Frank Schweizer
DOI: 10.1016/J.CARRES.2010.04.017
关键词:
摘要: Conformationally constrained amino acid analogs are widely used to probe the bioactive conformation of peptides. In this paper we report on synthesis hexafunctional allose-templated L- and D-hydroxyornithine D-hydroxyarginine in which allose-based polyol scaffold constrains side chain hydroxyornithine hydroxyarginine an extended conformation. The partially protected building blocks were selected for future use solid-phase peptide using Fmoc-strategy. starts from a previously prepared C-glucosyl glycine analog. Multiple chemical protection-deprotection steps oxidation prepare 3-keto-C-glucosyl that serve as precursor install function via reductive amination. Guanidinylation group provides access analogs. Both further chemically modified provide suitable protection
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