Synthesis of 1′-(4′-Thio-β-d-Ribofuranosyl) Uracil

Mieke Guinan; Gavin J. Miller; Dylan Lynch; Mark Smith

doi:10.1201/9781351256087-28

Synthesis of 1′-(4′-Thio-β-d-Ribofuranosyl) Uracil

Mieke Guinan
, Gavin J. Miller
, Dylan Lynch
, Mark Smith

Biological Chemistry and Drug Discovery

Research output: Chapter in Book/Report/Conference proceeding › Chapter (peer-reviewed) › peer-review

Abstract

4'-Thionucleosides, where the furanose ring oxygen is replaced with sulfur, have attracted significant interest due to their biological activity and metabolic stability. In recent years, a growing number of reports have detailed the chemical synthesis and evaluation of 4'-thio nucleoside analogs, alongside methodologies for the provision of thiosugar-containing scaffolds. The original report for synthesizing was made by Imbach and coworkers in their synthesis of 4'-thio-ß-d-oligoribonucleotides and utilized as the starting material, recording a 38% yield for the two-step process. NMR analysis confirmed the correct structure notably with the presence of signals for the alkene in the nucleobase with vicinal coupling to each other.

Original language	English
Title of host publication	Carbohydrate Chemistry
Subtitle of host publication	Proven Synthetic Methods
Editors	Paul Kosma, Tanja Wrodnigg, Arnold Stütz
Place of Publication	Boca Raton
Publisher	CRC Press
Chapter	28
Number of pages	6
Volume	5
Edition	1
ISBN (Electronic)	9781351256087
ISBN (Print)	9780815367888 (hbk), 9780367561734 (pbk)
DOIs	https://doi.org/10.1201/9781351256087-28
Publication status	Published - 2021

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title = "Synthesis of 1′-(4′-Thio-β-d-Ribofuranosyl) Uracil",

abstract = "4'-Thionucleosides, where the furanose ring oxygen is replaced with sulfur, have attracted significant interest due to their biological activity and metabolic stability. In recent years, a growing number of reports have detailed the chemical synthesis and evaluation of 4'-thio nucleoside analogs, alongside methodologies for the provision of thiosugar-containing scaffolds. The original report for synthesizing was made by Imbach and coworkers in their synthesis of 4'-thio-{\ss}-d-oligoribonucleotides and utilized as the starting material, recording a 38\% yield for the two-step process. NMR analysis confirmed the correct structure notably with the presence of signals for the alkene in the nucleobase with vicinal coupling to each other.",

author = "Mieke Guinan and Miller, \{Gavin J.\} and Dylan Lynch and Mark Smith",

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doi = "10.1201/9781351256087-28",

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TY - CHAP

T1 - Synthesis of 1′-(4′-Thio-β-d-Ribofuranosyl) Uracil

AU - Guinan, Mieke

AU - Miller, Gavin J.

AU - Lynch, Dylan

AU - Smith, Mark

PY - 2021

Y1 - 2021

N2 - 4'-Thionucleosides, where the furanose ring oxygen is replaced with sulfur, have attracted significant interest due to their biological activity and metabolic stability. In recent years, a growing number of reports have detailed the chemical synthesis and evaluation of 4'-thio nucleoside analogs, alongside methodologies for the provision of thiosugar-containing scaffolds. The original report for synthesizing was made by Imbach and coworkers in their synthesis of 4'-thio-ß-d-oligoribonucleotides and utilized as the starting material, recording a 38% yield for the two-step process. NMR analysis confirmed the correct structure notably with the presence of signals for the alkene in the nucleobase with vicinal coupling to each other.

AB - 4'-Thionucleosides, where the furanose ring oxygen is replaced with sulfur, have attracted significant interest due to their biological activity and metabolic stability. In recent years, a growing number of reports have detailed the chemical synthesis and evaluation of 4'-thio nucleoside analogs, alongside methodologies for the provision of thiosugar-containing scaffolds. The original report for synthesizing was made by Imbach and coworkers in their synthesis of 4'-thio-ß-d-oligoribonucleotides and utilized as the starting material, recording a 38% yield for the two-step process. NMR analysis confirmed the correct structure notably with the presence of signals for the alkene in the nucleobase with vicinal coupling to each other.

U2 - 10.1201/9781351256087-28

DO - 10.1201/9781351256087-28

M3 - Chapter (peer-reviewed)

SN - 9780815367888 (hbk)

SN - 9780367561734 (pbk)

VL - 5

BT - Carbohydrate Chemistry

A2 - Kosma, Paul

A2 - Wrodnigg, Tanja

A2 - Stütz, Arnold

PB - CRC Press

CY - Boca Raton

ER -

Synthesis of 1′-(4′-Thio-β-d-Ribofuranosyl) Uracil

Abstract

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