5-(Ferrocene-1-yl-ethynyl)-2′-deoxyuridinetriphosphate – CAS 1007229-84-6

5-(Ferrocene-1-yl-ethynyl)-2′-deoxyuridinetriphosphate – CAS 1007229-84-6 was synthesized and licensed at the IOCB Prague, lab of prof. Michal Hocek.

Purity (LC-MS)

99 %

Package contents

5-(Ferrocene-1-yl-ethynyl)-2′-deoxyuridine triphosphate Na+ salt

This compound is for research use only. We do not sell to patients.

Amount
1 mg
€ 1400

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5 mg
€ 3500

Stock

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Amount
1 mg
€ 1400

Stock

5 mg
€ 3500

Stock

Do you want custom amount?
Custom amount

Characterisation

CAS: 1007229-84-6
IUPAC name: 5-(Ferrocene-1-yl-ethynyl)-2′-deoxyuridinetriphosphate
Molecular weight: 676.18 g/mol
Molecular formula: C21H23FeN2O14P3
InChI: InChI=1S/C16H18N2O14P3.C5H5.Fe/c19-12-7-14(18-8-11(15(20)17-16(18)21)6-5-10-3-1-2-4-10)30-13(12)9-29-34(25,26)32-35(27,28)31-33(22,23)24;1-2-4-5-3-1;/h1-4,8,12-14,19H,7,9H2,(H,25,26)(H,27,28)(H,17,20,21)(H2,22,23,24);1-5H;/q2*-1;+2
Storage: -20 °C, protect from light

Description

5-(Ferrocene-1-yl-ethynyl)-2′-deoxyuridinetriphosphate is a ferrocene labeled analog of natural uridine triphosphate. Ferrocene is used as the gold standard for electrochemical labeling. Its conjugation at 5- position of uridine triphosphate allows enzymatic incorporation of such analog in primer extension reactions and PCR. The compound might be used for electrochemical redox labeling of DNA, site-specific redox labeling, or in the development of highly sensitive genosensors.

5-(Ferrocene-1-yl-ethynyl)-2′-deoxyuridine triphosphate was synthesized and licensed at the IOCB Prague, lab of prof. Michal Hocek. 

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References

  • Brázdilová, P.; Vrábel, M.; Pohl, R.; Pivoňková, H.; Havran, L.; Hocek, M.; Fojta, M., Ferrocenylethynyl Derivatives of Nucleoside Triphosphates: Synthesis, Incorporation, Electrochemistry, and Bioanalytical Applications. Chemistry – A European Journal 2007, 13 (34), 9527-9533.
  • Ménová, P.; Cahová, H.; Plucnara, M.; Havran, L.; Fojta, M.; Hocek, M., Polymerase synthesis of oligonucleotides containing a single chemically modified nucleobase for site-specific redox labelling. Chemical Communications 2013, 49 (41), 4652-4654.
  • Magriñá, I.; Toldrà, A.; Campàs, M.; Ortiz, M.; Simonova, A.; Katakis, I.; Hocek, M.; O’Sullivan, C. K., Electrochemical genosensor for the direct detection of tailed PCR amplicons incorporating ferrocene labelled dATP. Biosensors and Bioelectronics 2019, 134, 76-82.
  • Simonova, A.; Magriñá, I.; Sýkorová, V.; Pohl, R.; Ortiz, M.; Havran, L.; Fojta, M.; O’Sullivan, C. K.; Hocek, M., Tuning of Oxidation Potential of Ferrocene for Ratiometric Redox Labeling and Coding of Nucleotides and DNA. Chemistry – A European Journal 2020, 26 (6), 1286-1291.
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