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T511293

Sigma-Aldrich

(2′S)-2′-Deoxy-2′-fluoro-5-ethynyluridine, (F-ara-EdU)

AldrichCPR

Synonym(s):

1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-ethynyl-2,4(1H,3H)-pyrimidinedione

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About This Item

Empirical Formula (Hill Notation):
C11H11FN2O5
CAS Number:
95740-26-4
Molecular Weight:
270.21
MDL number:
MFCD22417248
UNSPSC Code:
12352200
PubChem Substance ID:
329826809

Quality Level

100

reaction suitability

reaction type: click chemistry

SMILES string

OC[C@H]1O[C@H]([C@@H](F)[C@@H]1O)N2C=C(C#C)C(=O)NC2=O

InChI

1S/C11H11FN2O5/c1-2-5-3-14(11(18)13-9(5)17)10-7(12)8(16)6(4-15)19-10/h1,3,6-8,10,15-16H,4H2,(H,13,17,18)/t6-,7+,8-,10-/m1/s1

InChI key

YEEGMPUOCRQFRV-IBCQBUCCSA-N

Related Categories

Application

A probe for DNA synthesis in vivo that is less toxic than both EdU and BrdU. Ideally suited for metabolic DNA labeling when prolonged cell survival and undisturbed cell cycle progression are required.

Other Notes

Please note that Sigma-Aldrich provides this product to early discovery researchers as part of a collection of unique chemicals. Sigma-Aldrich does not collect analytical data for this product. Buyer assumes responsibility to confirm product identity and/or purity. All sales are final.

NOTWITHSTANDING ANY CONTRARY PROVISION CONTAINED IN SIGMA-ALDRICH′S STANDARD TERMS AND CONDITIONS OF SALE OR AN AGREEMENT BETWEEN SIGMA-ALDRICH AND BUYER, SIGMA-ALDRICH SELLS THIS PRODUCT "AS-IS" AND MAKES NO REPRESENTATION OR WARRANTY WHATSOEVER WITH RESPECT TO THIS PRODUCT, INCLUDING ANY (A) WARRANTY OF MERCHANTABILITY; (B) WARRANTY OF FITNESS FOR A PARTICULAR PURPOSE; OR (C) WARRANTY AGAINST INFRINGEMENT OF INTELLECTUAL PROPERTY RIGHTS OF A THIRD PARTY; WHETHER ARISING BY LAW, COURSE OF DEALING, COURSE OF PERFORMANCE, USAGE OF TRADE OR OTHERWISE.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Anne B Neef et al.
Proceedings of the National Academy of Sciences of the United States of America, 108(51), 20404-20409 (2011-12-07)
Commonly used metabolic labels for DNA, including 5-ethynyl-2'-deoxyuridine (EdU) and BrdU, are toxic antimetabolites that cause DNA instability, necrosis, and cell-cycle arrest. In addition to perturbing biological function, these properties can prevent metabolic labeling studies where subsequent tissue survival is
Florence D D'Orazi et al.
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Luedtke Group – Professor Product Portal

Metabolic incorporation of a bioorthogonal functional group (e.g. alkyne, azide, alkene, etc.) into cellular DNA can be achieved by simply adding a synthetic nucleoside to the nutritional media of cells or whole animals.

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