Synthesis of Piperidine Nucleosides as Conformationally Restricted Immucillin Mimics

Molecules

MariaDe Fenza¹  Anna Esposito¹  Daniele D’Alonzo¹  Annalisa Guaragna² 

[1] Department of Chemical Sciences, University of Naples Federico II, Via Cintia, 80126 Naples, Italy;Department of Chemical, Materials and Production Engineering, University of Naples Federico II, Piazzale V. Tecchio 80, 80125 Naples, Italy;

关键词: immucillins;    nucleoside analogues;    de novo synthesis;    iminosugars;    biomimetics;    conformationally restricted nucleosides;   

DOI  :  10.3390/molecules26061652

来源: DOAJ

【 摘 要 】

The de novo synthesis of piperidine nucleosides from our homologating agent 5,6-dihydro-1,4-dithiin is herein reported. The structure and conformation of nucleosides were conceived to faithfully resemble the well-known nucleoside drugs Immucillins H and A in their bioactive conformation. NMR analysis of the synthesized compounds confirmed that they adopt an iminosugar conformation bearing the nucleobases and the hydroxyl groups in the appropriate orientation.

【 授权许可】

Unknown