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Steric and Stereoscopic Disulfide Construction for Cross-linkage via N-Dithiophthalimides

Abstract

Disulfide bond is a significant motif in life and drug-delivery systems. Especially, steric hindrance and stereoscopic disulfide linkers are closely associated with the stability of antibody-drug conjugates, which affects the potency, selectivity, and pharmacokinetics of drugs. However, limited availability and diversity of tertiary thiols impede the construction of steric and stereoscopic disulfides for cross-linkage in biochemistry and pharmaceuticals. Through modulating mask effect of disulfurating reagents, we develop a facile and robust strategy for diverse steric and stereoscopic disulfides construction via N-dithiophthalimides. The practical cross-linkage of biomolecules including amino acids, saccharides, and nucleosides with different drugs and fluorescent molecules is successfully established through hindered disulfide linkers.

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Article information


Submitted
22 Feb 2020
Accepted
20 Mar 2020
First published
20 Mar 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Accepted Manuscript
Article type
Edge Article

Steric and Stereoscopic Disulfide Construction for Cross-linkage via N-Dithiophthalimides

W. Gao, J. Tian, Y. Shang and X. Jiang, Chem. Sci., 2020, Accepted Manuscript , DOI: 10.1039/D0SC01060J

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