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Use of solid-supported 4-fluorophenyl 3-nitro-2-pyridinesulfenate in the construction of disulfide-linked hybrid molecules†
Yan Cui,Akihiro Taguchi,Kiyotaka Kobayashi,Hayate Shida,Kentaro Takayama,Atsuhiko Taniguchi,Yoshio Hayashi
Organic & Biomolecular Chemistry Pub Date : 09/07/2020 00:00:00 , DOI:10.1039/D0OB01370F
Abstract

To construct disulfide-linked hybrid molecules systematically and efficiently, we established a more practical solid-phase disulfide ligation (SPDSL) system with enhanced utility. The group Npys-OPh(pF) shows reactivity similar to that of Npys-Cl, but it is more stable. An efficient synthesis of the cyclic peptide oxytocin and a peptide–sugar conjugate was accomplished as models. These results indicate that the Npys-OPh(pF) resin functions as a common synthetic platform in SPDSL.

Graphical abstract: Use of solid-supported 4-fluorophenyl 3-nitro-2-pyridinesulfenate in the construction of disulfide-linked hybrid molecules
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