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323624

2′,3′-Dideoxyuridine

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

98%

Synonym(s):

ddU

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About This Item

Empirical Formula (Hill Notation):

C₉H₁₂N₂O₄

CAS Number:

5983-09-5

Molecular Weight:

212.20

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

24859406

MDL number:

MFCD00013359

Beilstein/REAXYS Number:

750592

Assay:

98%

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Properties

assay

98%

optical activity

[α]20/D +34°, c = 0.4 in H₂O

mp

127-129 °C (lit.)

functional group

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

InChI key

BTOTXLJHDSNXMW-POYBYMJQSA-N

Description

Application

Research tool for antiviral and anticancer studies.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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

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

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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Global Trade Item Number

SKU	GTIN
323624-100MG	04061832913001
323624-500MG	04061832913018