Synthesis of 4-mercapto-L-lysine derivatives: potential building blocks for sequential native chemical ligation

Kalyan Kumar Pasunooti; Renliang Yang; Seenuvasan Vedachalam; Bala Kishan Gorityala; Chuan-Fa Liu; Xue-Wei Liu

doi:10.1016/j.bmcl.2009.09.107

Synthesis of 4-mercapto-L-lysine derivatives: potential building blocks for sequential native chemical ligation

Bioorg Med Chem Lett. 2009 Nov 15;19(22):6268-71. doi: 10.1016/j.bmcl.2009.09.107. Epub 2009 Oct 3.

Authors

Kalyan Kumar Pasunooti¹, Renliang Yang, Seenuvasan Vedachalam, Bala Kishan Gorityala, Chuan-Fa Liu, Xue-Wei Liu

Affiliation

¹ Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.

PMID: 19833511
DOI: 10.1016/j.bmcl.2009.09.107

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antiviral Agents / chemical synthesis*
Catalysis
Crystallography, X-Ray
Esters / chemistry
Lysine / analogs & derivatives
Lysine / chemistry*
Peptide Fragments / chemistry
Pharmaceutical Preparations / chemical synthesis*
Pharmaceutical Preparations / chemistry
Sulfhydryl Compounds / chemistry

Substances

Antiviral Agents
Esters
Peptide Fragments
Pharmaceutical Preparations
Sulfhydryl Compounds
Lysine