Syntheses of Biologically Relevant Reactive Sulfur Species by Utilizing a Primary Alkyl Steric Protection Group

Abstract

A novel primary alkyl steric protection group (BpqCH₂ group) bearing a cavity-shaped framework was designed and successfully applied to the stabilization of a sulfenyl iodide. The sulfenyl iodide showed remarkable stability, demonstrating that the BpqCH₂ group is very effective for kinetic stabilization of primary-alkyl-substituted reactive species.

Keywords:

• Cysteine models
• reactive sulfur species
• steric protection
• sulfenyl iodides

Acknowledgments

This work was partly supported by Grants-in-Aid for the Global COE Program for Education and Research Center for Emergence of New Molecular Chemistry and for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan. We also acknowledge supports from Toray Science Foundation and The Society of Iodine Science.