title: Synthesis of 4-mercapto-L-lysine derivatives: potential building blocks for sequential native chemical ligation.
abstract: A general and diastereoselective synthesis of (2S, 4S)-4-mercapto-L-lysine derivative was described. The key features of this synthesis include Zn-mediated diastereoselective Reformatsky reaction and selective reduction of methyl ester with sodium borohydride. Introduction of thiol functional group on lysine side chain proved to be appropriate for dual native chemical ligation. This methodology allows to develop various 4-substituted L-lysine derivatives.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
authors.forename: Kalyan Kumar
authors.initials: KK
authors.lastname: Pasunooti
authors.forename: Renliang
authors.initials: R
authors.lastname: Yang
authors.forename: Seenuvasan
authors.initials: S
authors.lastname: Vedachalam
authors.forename: Bala Kishan
authors.initials: BK
authors.lastname: Gorityala
authors.forename: Chuan-Fa
authors.initials: CF
authors.lastname: Liu
authors.forename: Xue-Wei
authors.initials: XW
authors.lastname: Liu
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis*; D002384:Catalysis; D018360:Crystallography, X-Ray; D004952:Esters / Q000737:chemistry; D008239:Lysine / Q000031:analogs & derivatives / Q000737:chemistry*; D010446:Peptide Fragments / Q000737:chemistry; D004364:Pharmaceutical Preparations / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry
chemical_list: D000998:Antiviral Agents; D004952:Esters; D010446:Peptide Fragments; D004364:Pharmaceutical Preparations; D013438:Sulfhydryl Compounds; D008239:Lysine