7-(Ferrocene-1-yl-ethynyl)-7-deaza-2′-deoxyadenosine triphosphate CAS 1007229-83-5

7-(Ferrocene-1-yl-ethynyl)-7-deaza-2′-deoxyadenosine triphosphate was synthesized and licensed at the IOCB Prague, lab of prof. Michal Hocek. 

Purity (LC-MS)

99 %

Package contents

7-(Ferrocene-1-yl-ethynyl)-7-deaza-2′-deoxyadenosine triphosphate Na+ salt

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

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Characterisation

CAS: 1007229-83-5

IUPAC Name: [2-[4-Amino-7-[2-deoxy-5-O-[hydroxy[[hydroxy(phosphonooxy)phosphinyl]oxy]phosphinyl]-β-D-erythro-pentofuranosyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl]ethynyl]ferrocene

Molecular weight: 698.2 g/mol; 764.2 (Na+ salt)

Molecular formula: C23H25FeN4O12P3

Storage: -20 °C, protect from light

 

Description

7-(Ferrocene-1-yl-ethynyl)-7-deaza-2′-deoxyadenosine triphosphate is a ferrocene-labeled analog of natural adenosine triphosphate. Ferrocene is used as the gold standard for electrochemical labeling. Its conjugation at 7- position of 7-deaza-2′-deoxyadenosine triphosphate allows enzymatic incorporation of such adenosine triphosphate 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.

The product was synthesized and licensed at the IOCB Prague, lab of prof. Michal Hocek.

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References

1. 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.
2. 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.
3. 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.
4. 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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