Synthesis of phosphonate and phostone analogues of ribose-1-phosphates

Pitak Nasomjai; David O'Hagan; Alexandra M. Z. Slawin

doi:10.3762/bjoc.5.37

Synthesis of phosphonate and phostone analogues of ribose-1-phosphates

Pitak Nasomjai, David O'Hagan, Alexandra M. Z. Slawin

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Abstract

The synthesis of phosphonate analogues of ribose-1-phosphate and 5-fluoro-5-deoxyribose-1-phosphate is described. Preparations of both the alpha- and beta-phosphonate anomers are reported for the ribose and 5-fluoro-5-deoxyribose series and a synthesis of the corresponding cyclic phostones of each alpha-ribose is also reported. These compounds have been prepared as tools to probe the details of fluorometabolism in S. cattleya.

Original language	English
Article number	37
Number of pages	7
Journal	Beilstein Journal of Organic Chemistry
Volume	5
DOIs	https://doi.org/10.3762/bjoc.5.37
Publication status	Published - 27 Jul 2009

Keywords

5-fluoro-5-deoxyribose-1-phosphate
fluorometabolite biosynthesis
phosphonates
phostone
ribose-1-phosphate
Biosynthesis
Fluorinase
Acid

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10.3762/bjoc.5.37

OHaganBeilsteinJOrgChem5 37
© 2009 Nasomjai et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)
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title = "Synthesis of phosphonate and phostone analogues of ribose-1-phosphates",

abstract = "The synthesis of phosphonate analogues of ribose-1-phosphate and 5-fluoro-5-deoxyribose-1-phosphate is described. Preparations of both the alpha- and beta-phosphonate anomers are reported for the ribose and 5-fluoro-5-deoxyribose series and a synthesis of the corresponding cyclic phostones of each alpha-ribose is also reported. These compounds have been prepared as tools to probe the details of fluorometabolism in S. cattleya.",

keywords = "5-fluoro-5-deoxyribose-1-phosphate, fluorometabolite biosynthesis, phosphonates, phostone, ribose-1-phosphate, Biosynthesis, Fluorinase, Acid",

author = "Pitak Nasomjai and David O'Hagan and Slawin, {Alexandra M. Z.}",

year = "2009",

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day = "27",

doi = "10.3762/bjoc.5.37",

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T1 - Synthesis of phosphonate and phostone analogues of ribose-1-phosphates

AU - Nasomjai, Pitak

AU - O'Hagan, David

AU - Slawin, Alexandra M. Z.

PY - 2009/7/27

Y1 - 2009/7/27

N2 - The synthesis of phosphonate analogues of ribose-1-phosphate and 5-fluoro-5-deoxyribose-1-phosphate is described. Preparations of both the alpha- and beta-phosphonate anomers are reported for the ribose and 5-fluoro-5-deoxyribose series and a synthesis of the corresponding cyclic phostones of each alpha-ribose is also reported. These compounds have been prepared as tools to probe the details of fluorometabolism in S. cattleya.

AB - The synthesis of phosphonate analogues of ribose-1-phosphate and 5-fluoro-5-deoxyribose-1-phosphate is described. Preparations of both the alpha- and beta-phosphonate anomers are reported for the ribose and 5-fluoro-5-deoxyribose series and a synthesis of the corresponding cyclic phostones of each alpha-ribose is also reported. These compounds have been prepared as tools to probe the details of fluorometabolism in S. cattleya.

KW - 5-fluoro-5-deoxyribose-1-phosphate

KW - fluorometabolite biosynthesis

KW - phosphonates

KW - phostone

KW - ribose-1-phosphate

KW - Biosynthesis

KW - Fluorinase

KW - Acid

U2 - 10.3762/bjoc.5.37

DO - 10.3762/bjoc.5.37

M3 - Article

SN - 1860-5397

VL - 5

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

M1 - 37

ER -

Synthesis of phosphonate and phostone analogues of ribose-1-phosphates

Abstract

Keywords

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