3′,4′-Didehydro-3′-deoxycytidine monophosphate – CAS 2499590-47-3

3′,4′-Didehydro-3′-deoxycytidine monophosphate – CAS 2499590-47-3 is synthesized by Sigut Labs (Prague, Czech Republic). 

Purity (LC-MS)

min 95%

Package contents

3′,4′-Didehydro-3′-deoxycytidine monophosphate triethylammonium salt

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

Amount
1 mg
€ 1500

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5 mg
€ 3000

Stock

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Custom amount
Amount
1 mg
€ 1500

Stock

5 mg
€ 3000

Stock

Do you want custom amount?
Custom amount

Characterisation

CAS: 2499590-47-3, 2657712-09-7 (Na+ salt)
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 monophosphate
Other names: 4-amino-1-[(2R,3R)-2,3-dihydro-3-hydroxy-5-(hydroxymethyl)-2-furanyl]-2(1H)-Pyrimidinone monophosphate, DdhCMP, DdhC-MP
Molecular weight: 305.18 g/mol
Molecular formula: C9H12N3O7P
InChI: InChI=1S/C9H12N3O7P/c10-7-1-2-12(9(14)11-7)8-6(13)3-5(19-8)4-18-20(15,16)17/h1-3,6,8,13H,4H2,(H2,10,11,14)(H2,15,16,17)/t6-,8-/m1/s1

Description

3′,4′-didehydro-3′-deoxycytidine monophosphate is a metabolite 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.

3′,4′-didehydro-3′-deoxycytidine monophosphate is provided as triethylammonium salt.

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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 B111(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 biotechnology19(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. Med3(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 Chemistry56(1), 48-55.
  • Bernheim, A., Millman, A., Ofir, G., Meitav, G., Avraham, C., Shomar, H., … & Sorek, R. (2021). Prokaryotic viperins produce diverse antiviral molecules. Nature589(7840), 120-124.
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