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3′,4′-Didehydro-3′-deoxycytidine – CAS 386264-46-6

3′,4′-Didehydro-3′-deoxycytidine – CAS 386264-46-6 is synthesized by Sigut Labs (Prague, Czech Republic).

Purity (LC-MS)

min 95%

Package contents

3′,4′-Didehydro-3′-deoxycytidine

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

Amount

10 mg	€ 400	Stock
100 mg	€ 1500	Stock
500 mg	€ 3000	Stock
Do you want custom amount?			Custom amount

Amount

10 mg

€ 400

Stock

100 mg

€ 1500

Stock

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Characterisation

CAS: 386264-46-6

IUPAC name: 2(1H)-Pyrimidinone, 4-amino-1-[(2R,3R)-2,3-dihydro-3-hydroxy-5-(hydroxymethyl)-2-furanyl]-4-Amino-1-[3-hydroxy-5-(hydroxymethyl)-2,3-dihydrofuran-2-yl]-1,2-dihydropyrimidin-2-one

Other names: 3′,4′-Didehydro-3′-deoxycytidine (ACI), 4-Amino-1-[(2R,3R)-2,3-dihydro-3-hydroxy-5-(hydroxymethyl)-2-furanyl]-2(1H)-Pyrimidinone, DdhC

Molecular weight: 225.20 g/mol

Molecular formula: C₉H₁₁N₃O₄

InChI: InChI=1S/C9H11N3O4/c10-7-1-2-12(9(15)11-7)8-6(14)3-5(4-13)16-8/h1-3,6,8,13-14H,4H2,(H2,10,11,15)/t6-,8-/m1/s1

Description

3′,4′-Didehydro-3′-deoxycytidine is an analogue of cytidine. It is a free base of 3′,4′-didehydro-3′-deoxycytidine triphosphate that has been proven to have an antiviral properties. It has the ability to prevent the replication of several viruses, including the Zika virus. This molecule is naturally produced in mammals through the dehydration of cytidine triphosphate (CTP), which is catalyzed by the enzyme viperin.

This product was developed as part of the European Union-funded grant program Czech Rise Up 3.0 – Výzkum medicínských řešení v době digitalizace.

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Payment

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References

Wang, F. (2007). Unsaturated Didehydrodeoxycytidine Drugs. 1. Impact of CC Positions in the Sugar Ring. The Journal of Physical Chemistry B, 111(32), 9628-9633.
Torrance, C. J., Agrawal, V., Vogelstein, B., & Kinzler, K. W. (2001). Use of isogenic human cancer cells for high-throughput screening and drug discovery. Nature biotechnology, 19(10), 940-945.
Mehta, R., Chekmeneva, E., Jackson, H., Sands, C., Mills, E., Arancon, D., … & Sriskandan, S. (2022). Antiviral metabolite 3′-deoxy-3′, 4′-didehydro-cytidine is detectable in serum and identifies acute viral infections including COVID-19. Med, 3(3), 204-215.
McGall, G. H., Stubbe, J., & Kozarich, J. W. (1991). Acyl migration in the production of thymine. Propenal from 3′-O-benzoyl-5′-deoxy-4′-(hydroperoxy) thymidine: a reinterpretation of a putative model for bleomycin-mediated DNA degradation. The Journal of Organic Chemistry, 56(1), 48-55.
Bernheim, A., Millman, A., Ofir, G., Meitav, G., Avraham, C., Shomar, H., … & Sorek, R. (2021). Prokaryotic viperins produce diverse antiviral molecules. Nature, 589(7840), 120-124.