title: A chiron approach towards the synthesis of 3-hydroxy lysine and its derivatives.
abstract: A general and efficient route towards the synthesis of three derivatives of structurally and functionally important amino acid, lysine is reported. Chemoselective reduction of aldehydic functionality in C-3-azido conjugated aldehyde 4, under Luche condition, is the key step in the synthetic sequence. The lysine derivative, (2S,3R)-2,6-diazido-3-hydroxy-hex-4-ene-oic acid 9 could be used to prepare switch peptide using Staudinger reaction, while the unprotected (2S,3R)-2,6-diamino-3-hydroxy-hexanoic acid hydrochloride 10 is a proven reaction intermediate towards the synthesis of natural product (-)-Balanol.
authors.affiliation: Bio-Organic Division, Bhabha Atomic Research Centre, Trombay, Mumbai 400085, India. ajish@barc.gov.in
authors.forename: K S Ajish
authors.initials: KS
authors.lastname: Kumar
mesh_terms: D008239:Lysine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D014765:Viral Vaccines / Q000737:chemistry*
chemical_list: D014765:Viral Vaccines; C409203:chiron; D008239:Lysine