Synthesis of a novel C-nucleoside, 2-amino-7-(2-deoxy-β-D-erythro- pentofuranosyl)-3H,5H-pyrrolo-[3,2-d]pyrimidin-4one (2'-deoxy-9- deazaguanosine)

Eric S. Gibson; Krystyna Lesiak; Kyoichi A. Watanabe; Lorraine J. Gudas; Krzysztof W. Pankiewicz

doi:10.1080/15257779908043082

Synthesis of a novel C-nucleoside, 2-amino-7-(2-deoxy-β-D-erythro- pentofuranosyl)-3H,5H-pyrrolo-[3,2-d]pyrimidin-4one (2'-deoxy-9- deazaguanosine)

Eric S. Gibson
, Krystyna Lesiak
, Kyoichi A. Watanabe
, Lorraine J. Gudas
, Krzysztof W. Pankiewicz

Center for Drug Design

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

A synthesis of the C-nucleoside, 2-amino-7-(2-deoxy-β-D- erythropentofuranosyl)-3H,5H-pyrrolo[3,2-d]pyrimidin-4-one (9-deaza-2'- deoxyguanosine) was achieved starting from 2-amino-6-methyl-3H-pyrimidin-4- one (5) and methyl 2-deoxy-3,5-di-O-(p-nitrobenzoyl)-D-erythro-pento- furanoside (11). The anomeric configuration of the C-nucleoside was established by ¹H NMR, NOEDS and ROESY. This C-nucleoside did not inhibit the growth of T-cell lymphoma cells.

Original language	English (US)
Pages (from-to)	363-376
Number of pages	14
Journal	Nucleosides and Nucleotides
Volume	18
Issue number	3
DOIs	https://doi.org/10.1080/15257779908043082
State	Published - 1999

Bibliographical note

Funding Information:
This investigation was supported in part by fund from the National Institutes of Health, U. S. Department of Health and Human Services grant 5F 31GM 17314 (to E.S.G.).

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SDG 3 Good Health and Well-being

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title = "Synthesis of a novel C-nucleoside, 2-amino-7-(2-deoxy-β-D-erythro- pentofuranosyl)-3H,5H-pyrrolo-[3,2-d]pyrimidin-4one (2'-deoxy-9- deazaguanosine)",

abstract = "A synthesis of the C-nucleoside, 2-amino-7-(2-deoxy-β-D- erythropentofuranosyl)-3H,5H-pyrrolo[3,2-d]pyrimidin-4-one (9-deaza-2'- deoxyguanosine) was achieved starting from 2-amino-6-methyl-3H-pyrimidin-4- one (5) and methyl 2-deoxy-3,5-di-O-(p-nitrobenzoyl)-D-erythro-pento- furanoside (11). The anomeric configuration of the C-nucleoside was established by 1H NMR, NOEDS and ROESY. This C-nucleoside did not inhibit the growth of T-cell lymphoma cells.",

author = "Gibson, \{Eric S.\} and Krystyna Lesiak and Watanabe, \{Kyoichi A.\} and Gudas, \{Lorraine J.\} and Pankiewicz, \{Krzysztof W.\}",

note = "Funding Information: This investigation was supported in part by fund from the National Institutes of Health, U. S. Department of Health and Human Services grant 5F 31GM 17314 (to E.S.G.).",

year = "1999",

doi = "10.1080/15257779908043082",

language = "English (US)",

volume = "18",

pages = "363--376",

journal = "Nucleosides and Nucleotides",

issn = "0732-8311",

publisher = "Marcel Dekker Inc.",

number = "3",

}

TY - JOUR

T1 - Synthesis of a novel C-nucleoside, 2-amino-7-(2-deoxy-β-D-erythro- pentofuranosyl)-3H,5H-pyrrolo-[3,2-d]pyrimidin-4one (2'-deoxy-9- deazaguanosine)

AU - Gibson, Eric S.

AU - Lesiak, Krystyna

AU - Watanabe, Kyoichi A.

AU - Gudas, Lorraine J.

AU - Pankiewicz, Krzysztof W.

N1 - Funding Information: This investigation was supported in part by fund from the National Institutes of Health, U. S. Department of Health and Human Services grant 5F 31GM 17314 (to E.S.G.).

PY - 1999

Y1 - 1999

N2 - A synthesis of the C-nucleoside, 2-amino-7-(2-deoxy-β-D- erythropentofuranosyl)-3H,5H-pyrrolo[3,2-d]pyrimidin-4-one (9-deaza-2'- deoxyguanosine) was achieved starting from 2-amino-6-methyl-3H-pyrimidin-4- one (5) and methyl 2-deoxy-3,5-di-O-(p-nitrobenzoyl)-D-erythro-pento- furanoside (11). The anomeric configuration of the C-nucleoside was established by 1H NMR, NOEDS and ROESY. This C-nucleoside did not inhibit the growth of T-cell lymphoma cells.

AB - A synthesis of the C-nucleoside, 2-amino-7-(2-deoxy-β-D- erythropentofuranosyl)-3H,5H-pyrrolo[3,2-d]pyrimidin-4-one (9-deaza-2'- deoxyguanosine) was achieved starting from 2-amino-6-methyl-3H-pyrimidin-4- one (5) and methyl 2-deoxy-3,5-di-O-(p-nitrobenzoyl)-D-erythro-pento- furanoside (11). The anomeric configuration of the C-nucleoside was established by 1H NMR, NOEDS and ROESY. This C-nucleoside did not inhibit the growth of T-cell lymphoma cells.

UR - https://www.scopus.com/pages/publications/0032894434

UR - https://www.scopus.com/pages/publications/0032894434#tab=citedBy

U2 - 10.1080/15257779908043082

DO - 10.1080/15257779908043082

M3 - Article

C2 - 10358941

AN - SCOPUS:0032894434

SN - 0732-8311

VL - 18

SP - 363

EP - 376

JO - Nucleosides and Nucleotides

JF - Nucleosides and Nucleotides

IS - 3

ER -

Synthesis of a novel C-nucleoside, 2-amino-7-(2-deoxy-β-D-erythro- pentofuranosyl)-3H,5H-pyrrolo-[3,2-d]pyrimidin-4one (2'-deoxy-9- deazaguanosine)

Abstract

Bibliographical note

UN SDGs

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