Use of solid-supported 4-fluorophenyl 3-nitro-2-pyridinesulfenate in the construction of disulfide-linked hybrid molecules. Issue 36 (15th September 2020)

• Record Type: Journal Article
• Authors: Cui, Yan; Taguchi, Akihiro; Kobayashi, Kiyotaka; Shida, Hayate; Takayama, Kentaro; Taniguchi, Atsuhiko; Hayashi, Yoshio
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 36(2020)
• Page Start: 7094
• Page End: 7097
• Publication Date: 2020-09-15
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob01370f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A new solid-supported 4-fluorophenyl 3-nitro-2-pyridinesulfenate is useful for the efficient synthesis of a cyclic peptide and a disulfide-linked glycoconjugate. 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( p F) 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( p F) resin functions as a common synthetic platform in SPDSL.