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Key Documents

Ursprungszeugnis (CoO)/Analysenzertifikate (CoA)

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323624

2′,3′-Didesoxyuridin

Name: 2′,3′-Didesoxyuridin
Brand: ALDRICH

98%

Synonym(e):

ddU

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About This Item

Empirische Formel (Hill-System):

C₉H₁₂N₂O₄

CAS-Nummer:

5983-09-5

Molekulargewicht:

212.20

Beilstein:

750592

MDL-Nummer:

MFCD00013359

UNSPSC-Code:

12352100

PubChem Substanz-ID:

24859406

NACRES:

NA.22

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tert-Butylhydroperoxid -Lösung

Assay

98%

Optische Aktivität

[α]20/D +34°, c = 0.4 in H₂O

mp (Schmelzpunkt)

127-129 °C (lit.)

Funktionelle Gruppe

ether
hydroxyl

SMILES String

OC[C@@H]1CC[C@@H](O1)N2C=CC(=O)NC2=O

InChI

1S/C9H12N2O4/c12-5-6-1-2-8(15-6)11-4-3-7(13)10-9(11)14/h3-4,6,8,12H,1-2,5H2,(H,10,13,14)/t6-,8+/m0/s1

InChIKey

BTOTXLJHDSNXMW-POYBYMJQSA-N

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Anwendung

Research tool for antiviral and anticancer studies.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

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Analysenzertifikate (COA)

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Production of 2',3'-dideoxyadenosine and 2',3'-dideoxyinosine from 2',3'-dideoxyuridine and the corresponding purine bases by resting cells of Escherichia coli AJ 2595.

H Shirae et al.

Applied and environmental microbiology, 55(2), 419-424 (1989-02-01)

A novel microbial method for the production of 2',3'-dideoxynucleosides by transdideoxyribosylation has been developed. By screening microorganisms producing 2',3'-dideoxyadenosine (DDA) from 2',3'-dideoxyuridine (DDU) and adenine, Escherichia coli AJ 2595 was selected as the best producer. Optimal pH and temperature for

Potent DNA chain termination activity and selective inhibition of human immunodeficiency virus reverse transcriptase by 2',3'-dideoxyuridine-5'-triphosphate.

Z Hao et al.

Molecular pharmacology, 37(2), 157-163 (1990-02-01)

2',3'-Dideoxyuridine (ddUrd) exhibits poor if any anti-human immunodeficiency virus (HIV) activity in ATH8 and MT-4 cells. This is in agreement with the failure of ddUrd to be efficiently anabolized intracellularly to its 5'-triphosphate metabolite. However, 2',3'-dideoxyuridine-5'-triphosphate (ddUTP) proved to be

Synthesis and biological evaluation of some 5-nitro- and 5-amino derivatives of 2'-deoxycytidine, 2',3'-dideoxyuridine, and 2',3'-dideoxycytidine.

Evelina Colacino et al.

Nucleosides, nucleotides & nucleic acids, 22(11), 2013-2026 (2003-12-19)

In this article, we describe the synthesis of 5-nitro-1-(2-deoxy-alpha-D-erythro-pentofuranosyl)cytosine (4alpha), 5-nitro-1-(2-deoxy-beta-D-erythro-pentofuranosyl)cytosine (4beta), 5-amino-1-(2-deoxy-alpha-D-erythro-pentofuranosyl)cytosine (5alpha), 5-nitro-1-(2-deoxy-beta-D-erythro-pentofuranosyl)cytosine (5beta), 5-nitro-1-(2,3-dideoxy-beta-D-ribofuranosyl)uracil (6beta), 5-amino-1-(2,3-dideoxy-alpha,beta-D-ribofuranosyl)uracil (7), 5-nitro-1-(2,3-dideoxy-alpha,beta-D-ribofuranosyl)cytosine (8) and 5-amino-1-(2,3-dideoxy-beta-D-ribofuranosyl)cytosine (9beta). The prepared compounds were tested for their activity against HIV and HBV viruses, but they

Design, synthesis, and anti-HIV activity of 2',3'-didehydro-2',3'-dideoxyuridine (d4U), 2',3'-dideoxyuridine (ddU) phosphoramidate 'ProTide' derivatives.

Youcef Mehellou et al.

Bioorganic & medicinal chemistry letters, 17(13), 3666-3669 (2007-05-09)

We report the synthesis of 2',3'-didehydro-2',3'-dideoxyuridine (d4U) and 2',3'-dideoxyuridine (ddU) phosphoramidate 'ProTide' derivatives and their evaluation against HIV-1 and HIV-2. In addition, we conducted molecular modeling studies on both d4U and ddU monophosphates to investigate their second phosphorylation process. The

Certain phosphoramidate derivatives of dideoxy uridine (ddU) are active against HIV and successfully by-pass thymidine kinase.

C McGuigan et al.

FEBS letters, 351(1), 11-14 (1994-08-29)

As part of our effort to deliver masked phosphates inside living cells we have discovered that certain phosphate triester derivatives of the inactive nucleoside analogue, dideoxy uridine (ddU) are inhibitors of HIV replication at microM levels. Moreover, we note that

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Key Documents

2′,3′-Didesoxyuridin

98%

About This Item

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Eigenschaften

Assay

Optische Aktivität

mp (Schmelzpunkt)

Funktionelle Gruppe

SMILES String

InChI

InChIKey

Beschreibung

Anwendung

Sicherheitshinweise

Lagerklassenschlüssel

WGK

Flammpunkt (°F)

Flammpunkt (°C)

Persönliche Schutzausrüstung

Dokumentation

Analysenzertifikate (COA)

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