Synthesis of 4-mercapto-L-lysine derivatives: potential building blocks for sequential native chemical ligation.
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.
Pasunooti
Kalyan Kumar
KK
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
Yang
Renliang
R
Vedachalam
Seenuvasan
S
Gorityala
Bala Kishan
BK
Liu
Chuan-Fa
CF
Liu
Xue-Wei
XW
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
D000998:Antiviral Agents; D004952:Esters; D010446:Peptide Fragments; D004364:Pharmaceutical Preparations; D013438:Sulfhydryl Compounds; D008239:Lysine