Stereodefined Synthesis of O3‘-Labeled Uracil Nucleosides. 3‘-[17O]-2‘-Azido-2‘-deoxyuridine 5‘-Diphosphate as a Probe for the Mechanism of Inactivation of Ribonucleotide Reductases
Тип публикации: Journal Article
Дата публикации: 2002-03-01
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
11895397
Organic Chemistry
Краткое описание
Thermolysis of a 2'-[(16)O]-O-benzoyl-[(17)O]-5'-O-(tert-butyldimethylsilyl)-O(2),3'-cyclouridine derivative gave the more stable 3'-[(17)O]-O-benzoyl-[(16)O]- 5'-O-(tert-butyldimethylsilyl)-O(2),2'-cyclouridine isomer, which was converted into 3'-[(17)O]-2'-azido-2'-deoxyuridine by deprotection and nucleophilic ring opening at C2' with lithium azide. The 5'-diphosphate was prepared by nucleophilic displacement of the 5'-O-tosyl group with tris(tetrabutylammonium) hydrogen pyrophosphate. Model reactions gave (16)O and (18)O isotopomers, and base-promoted hydrolysis of an O(2),2'-cyclonucleoside gave stereodefined access to 3'-[(18)O]-1-(beta-D-arabinofuranosyl)uracil. Inactivation of ribonucleoside diphosphate reductase with 2'-azido-2'-deoxynucleotides results in appearance of EPR signals for a nitrogen-centered radical derived from azide, and 3'-[(17)O]-2'-azido-2'-deoxyuridine 5'-diphosphate provides an isotopomer to perturb EPR spectra in a predictable manner.
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Wnuk S. F. et al. Stereodefined Synthesis of O3‘-Labeled Uracil Nucleosides. 3‘-[17O]-2‘-Azido-2‘-deoxyuridine 5‘-Diphosphate as a Probe for the Mechanism of Inactivation of Ribonucleotide Reductases // Journal of Organic Chemistry. 2002. Vol. 67. No. 6. pp. 1816-1819.
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Wnuk S. F., Chowdhury S. M., Garcia P. I., Robins M. J. Stereodefined Synthesis of O3‘-Labeled Uracil Nucleosides. 3‘-[17O]-2‘-Azido-2‘-deoxyuridine 5‘-Diphosphate as a Probe for the Mechanism of Inactivation of Ribonucleotide Reductases // Journal of Organic Chemistry. 2002. Vol. 67. No. 6. pp. 1816-1819.
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TY - JOUR
DO - 10.1021/jo010899i
UR - https://doi.org/10.1021/jo010899i
TI - Stereodefined Synthesis of O3‘-Labeled Uracil Nucleosides. 3‘-[17O]-2‘-Azido-2‘-deoxyuridine 5‘-Diphosphate as a Probe for the Mechanism of Inactivation of Ribonucleotide Reductases
T2 - Journal of Organic Chemistry
AU - Wnuk, Stanislaw F.
AU - Chowdhury, Saiful M.
AU - Garcia, Pedro I
AU - Robins, Morris J.
PY - 2002
DA - 2002/03/01
PB - American Chemical Society (ACS)
SP - 1816-1819
IS - 6
VL - 67
PMID - 11895397
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2002_Wnuk,
author = {Stanislaw F. Wnuk and Saiful M. Chowdhury and Pedro I Garcia and Morris J. Robins},
title = {Stereodefined Synthesis of O3‘-Labeled Uracil Nucleosides. 3‘-[17O]-2‘-Azido-2‘-deoxyuridine 5‘-Diphosphate as a Probe for the Mechanism of Inactivation of Ribonucleotide Reductases},
journal = {Journal of Organic Chemistry},
year = {2002},
volume = {67},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/jo010899i},
number = {6},
pages = {1816--1819},
doi = {10.1021/jo010899i}
}
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MLA
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Wnuk, Stanislaw F., et al. “Stereodefined Synthesis of O3‘-Labeled Uracil Nucleosides. 3‘-[17O]-2‘-Azido-2‘-deoxyuridine 5‘-Diphosphate as a Probe for the Mechanism of Inactivation of Ribonucleotide Reductases.” Journal of Organic Chemistry, vol. 67, no. 6, Mar. 2002, pp. 1816-1819. https://doi.org/10.1021/jo010899i.