title: Synthesis of an azido precursor to (2S,5R)-5-hydroxylysine using an asymmetric organocatalytic chlorination/reduction sequence.
abstract: An efficient, robust, and scalable synthesis of an azido precursor to the modified amino acid (2S,5R)-5-hydroxylysine was developed on the basis of the use of a highly stereoselective organocatalytic α-chlorination-reduction protocol. The final Fmoc-protected (2S,5R)-6-azido-5-hydroxylysine derivative can be used in solid-phase peptide synthesis, providing access to proteins that contain large quantities of post-translationally modified lysine (e.g., collagens).
authors.affiliation: School of Chemical Sciences, The University of Auckland , 23 Symonds Street, Auckland 1142, New Zealand.
authors.forename: Manuel
authors.initials: M
authors.lastname: Johannes
authors.forename: Margaret A
authors.initials: MA
authors.lastname: Brimble
mesh_terms: D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D006901:Hydroxylysine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001386:Azides; D010455:Peptides; D006901:Hydroxylysine