volume 2019 issue 41 pages 6999-7004

Enzymatic Synthesis of 2-Deoxyribose 1-Phosphate and Ribose 1 Phosphate and Subsequent Preparation of Nucleosides

Publication typeJournal Article
Publication date2019-10-24
scimago Q2
wos Q2
SJR0.558
CiteScore4.3
Impact factor2.7
ISSN1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract

α‐Ribose‐1‐phosphate (Rib‐p) and 2‐deoxy‐α‐ribose‐1‐phosphate (dRib‐p) are key intermediates in nucleoside metabolism and are important starting compounds for the enzymatic synthesis of various modified nucleosides. To date, chemical and enzymatic methods allowed the preparation of these compounds in rather low yields (11–37 %). This prevents their widespread use for the enzymatic synthesis of biologically active and practically important nucleosides. Here we propose to use 7‐methyl‐2′‐deoxyguanosine (7‐Me‐dGuo) and 7‐methylguanosine (7‐Me‐Guo) for the preparation of dRib‐p and Rib‐p. In this paper, we present the effective preparation of Rib‐p and dRib‐p starting from readily prepared 7‐methylguanosine derivatives via their irreversible enzymatic phosphorolysis in the presence of purine nucleoside phosphorylase. Rib‐p and dRib‐P are obtained in nearly quantitative yields (HPLC analysis) and 74–96 % yields after their isolation and purification, which is much higher than previously reported.

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GOST Copy
Kulikova I. V. et al. Enzymatic Synthesis of 2-Deoxyribose 1-Phosphate and Ribose 1 Phosphate and Subsequent Preparation of Nucleosides // European Journal of Organic Chemistry. 2019. Vol. 2019. No. 41. pp. 6999-7004.
GOST all authors (up to 50) Copy
Kulikova I. V., Drenichev M. S., Solyev P. N., Alexeev C. S., Mikhailov S. N. Enzymatic Synthesis of 2-Deoxyribose 1-Phosphate and Ribose 1 Phosphate and Subsequent Preparation of Nucleosides // European Journal of Organic Chemistry. 2019. Vol. 2019. No. 41. pp. 6999-7004.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1002/ejoc.201901454
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201901454
TI - Enzymatic Synthesis of 2-Deoxyribose 1-Phosphate and Ribose 1 Phosphate and Subsequent Preparation of Nucleosides
T2 - European Journal of Organic Chemistry
AU - Kulikova, Irina V.
AU - Drenichev, M. S.
AU - Solyev, Pavel N.
AU - Alexeev, Cyril S
AU - Mikhailov, Sergey N.
PY - 2019
DA - 2019/10/24
PB - Wiley
SP - 6999-7004
IS - 41
VL - 2019
SN - 1434-193X
SN - 1099-0690
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2019_Kulikova,
author = {Irina V. Kulikova and M. S. Drenichev and Pavel N. Solyev and Cyril S Alexeev and Sergey N. Mikhailov},
title = {Enzymatic Synthesis of 2-Deoxyribose 1-Phosphate and Ribose 1 Phosphate and Subsequent Preparation of Nucleosides},
journal = {European Journal of Organic Chemistry},
year = {2019},
volume = {2019},
publisher = {Wiley},
month = {oct},
url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201901454},
number = {41},
pages = {6999--7004},
doi = {10.1002/ejoc.201901454}
}
MLA
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MLA Copy
Kulikova, Irina V., et al. “Enzymatic Synthesis of 2-Deoxyribose 1-Phosphate and Ribose 1 Phosphate and Subsequent Preparation of Nucleosides.” European Journal of Organic Chemistry, vol. 2019, no. 41, Oct. 2019, pp. 6999-7004. https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201901454.