Late-stage gem -difluoroallylation of phenol in bioactive molecules and peptides with 3,3-difluoroallyl sulfonium salts.

Autor:	Zhou M; College of Chemistry and Henan Institute of Advanced Technology, Zhengzhou University Zhengzhou 450001 China., Ren JX; Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials (Chinese Academy of Sciences), Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences 345 Lingling Road Shanghai 200032 China xgzhang@mail.sioc.ac.cn., Feng XT; College of Chemistry and Henan Institute of Advanced Technology, Zhengzhou University Zhengzhou 450001 China., Zhao HY; Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials (Chinese Academy of Sciences), Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences 345 Lingling Road Shanghai 200032 China xgzhang@mail.sioc.ac.cn., Fu XP; Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials (Chinese Academy of Sciences), Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences 345 Lingling Road Shanghai 200032 China xgzhang@mail.sioc.ac.cn., Min QQ; Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials (Chinese Academy of Sciences), Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences 345 Lingling Road Shanghai 200032 China xgzhang@mail.sioc.ac.cn., Zhang X; College of Chemistry and Henan Institute of Advanced Technology, Zhengzhou University Zhengzhou 450001 China.; Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials (Chinese Academy of Sciences), Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences 345 Lingling Road Shanghai 200032 China xgzhang@mail.sioc.ac.cn.
Jazyk:	angličtina
Zdroj:	Chemical science [Chem Sci] 2024 Jan 15; Vol. 15 (8), pp. 2937-2945. Date of Electronic Publication: 2024 Jan 15 (Print Publication: 2024).
DOI:	10.1039/d3sc06302j
Abstrakt:	An efficient method for the late-stage selective O -fluoroalkylation of tyrosine residues with a stable yet highly reactive fluoroalkylating reagent, 3,3-difluoroallyl sulfonium salts (DFASs), has been developed. The reaction proceeds in a mild basic aqueous buffer (pH = 11.6) with high efficiency, high biocompatibility, and excellent regio- and chemoselectivity. Various oligopeptides and phenol-containing bioactive molecules, including carbohydrates and nucleosides, could be selectively O -fluoroalkylated. The added vinyl and other functional groups from DFASs can be valuable linkers for successive modification, significantly expanding the chemical space for further bioconjugation. The synthetic utility of this protocol has been demonstrated by the fluorescently labeled anti-cancer drug and the synthesis of O-link type 1,4,7,10-tetraazacyclododecane- N , N ', N , N '-tetraacetic acid-tyrosine 3 -octreotate (DOTA-TATE), showing the prospect of the method in medicinal chemistry and chemical biology. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.)
Databáze:	MEDLINE
Externí odkaz:	Zobrazit plný text záznamu