Chemoselective Disulfide Formation by Thiol-Disulfide Interchange in SIT-Protected Cysteinyl Peptides.

Amit Chakraborty, Fernando Albericio, Beatriz G de la Torre

The Journal of organic chemistry 2022 Jan 07

filter terms:

Chemoselective disulfide formation is accomplished through a thiol-disulfide interchange approach using sec-isoamyl mercaptan (SIT) as an alkyl sulfenyl-protecting group of one of the Cys residues involved in the pairing. SIT has a dual and unique characteristic, acting as a masking group during the synthesis and directing disulfide formation in the presence of a free thiol. This novel approach is illustrated by the synthesis of several peptides of biological interest.

Citation

Amit Chakraborty, Fernando Albericio, Beatriz G de la Torre. Chemoselective Disulfide Formation by Thiol-Disulfide Interchange in SIT-Protected Cysteinyl Peptides. The Journal of organic chemistry. 2022 Jan 07;87(1):708-712