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 con-formation. NMR analysis of the synthesized compounds confirmed that they adopt an iminosugar conformation bearing the nucleobases and the hydroxyl groups in the appropriate orientation.
Synthesis of piperidine nucleosides as conformationally restricted immucillin mimics / DE FENZA, Maria; Esposito, Anna; D'Alonzo, Daniele; Guaragna, Annalisa. - In: MOLECULES. - ISSN 1420-3049. - 26:6(2021), p. 1652. [10.3390/molecules26061652]
Synthesis of piperidine nucleosides as conformationally restricted immucillin mimics
Maria De FenzaPrimo
;Anna Esposito;Daniele D'Alonzo;Annalisa Guaragna
Ultimo
2021
Abstract
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 con-formation. NMR analysis of the synthesized compounds confirmed that they adopt an iminosugar conformation bearing the nucleobases and the hydroxyl groups in the appropriate orientation.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.