A Synthetic Pathway to Cys-Xxx-Cys (N₂S₂) Analogue Ligands: An Improved Synthesis of HSCH₂CH₂C(O)NHCH₂C(O)NHCH₂CH₂SH

Abstract

Herein, two improved synthetic pathways to biologically relevant Cys-Xxx-Cys analogue ligands used in conjunction with metals as metalloenzyme models (Ni for carbon monoxide dehydrogenase/acetyl-CoA synthase A-cluster; Co and Fe for nitrile hydratase) are reported.

Keywords:

• Carboxamido ligand
• metal thiolate
• peptide synthesis
• synthetic analogue

Acknowledgments

Funding for this research was provided by the Research Corporation Cottrell College Grant 6600, American Philosophical Society; Franklin Research grant; and the Bureau of Faculty Research at Western Washington University. The authors would like to thank the Dreyfus Foundation: Faculty Startup Award (glovebox and solvent purification system) and the National Science Foundation: MRI grant NSF-0216604 (500 MHz NMR) for equipment funding. Ms. Angelosante would like to thank the Dreyfus Foundation for funding through the Jean Dreyfus Boissevain Undergraduate Scholarship.