633-90-9

Basic information

• Product Name: cytidine 2',3'-(hydrogen phosphate)
• Synonyms: cytidine 2',3'-(hydrogen phosphate);Cifostodine;2',3'-cCMP;Cyd-2',3'-P;Cytidine, cyclic 2',3'-(hydrogen phosphate);2',3'-cyclic CMP
• CAS NO: 633-90-9
• Molecular Formula: C₉H₁₂N₃O₇P
• Molecular Weight: 305.182
• EINECS: 211-198-5
• Mol File: 633-90-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 568.5°C at 760 mmHg
• Flash Point: 297.6°C
• Appearance: /
• Density: 2.28g/cm³
• Vapor Pressure: 2.72E-15mmHg at 25°C
• Refractive Index: 1.852
• PKA: 0.92±0.60(Predicted)
• CAS DataBase Reference: cytidine 2',3'-(hydrogen phosphate)(CAS DataBase Reference)
• NIST Chemistry Reference: cytidine 2',3'-(hydrogen phosphate)(633-90-9)
• EPA Substance Registry System: cytidine 2',3'-(hydrogen phosphate)(633-90-9)

Safety Data

• Hazardous Substances Data: 633-90-9(Hazardous Substances Data)

Usage

Definition

ChEBI: A 2',3'-cyclic pyrimidine nucleotide in which cytidine is the parent nucleoside.

InChI:InChI=1/C9H12N3O7P/c10-5-1-2-12(9(14)11-5)8-7-6(4(3-13)17-8)18-20(15,16)19-7/h1-2,4,6-8,13H,3H2,(H,15,16)(H2,10,11,14)/t4-,6-,7-,8-/m1/s1

Upstream product

• 84-52-6 cytidine 3'-monophosphate 
• 85-94-9 cytidine-2'-monophosphate 
• 2382-66-3 Cytidin-(3',5')-adenosin 
• 2382-65-2 [5']guanylic acid cytidin-3'-yl ester 
• 24601-74-9 (S)-4-isopropyloxazolidine-2,5-dione 
• 22886-38-0 Phosphoric acid (2R,3S,4R,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester (2R,3R,4R,5R)-2-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester 
• 4850-55-9 2,2,2-trimethoxy-4,5-diphenyl-2,2-dihydro-1,3,2-dioxaphospholene 
• 65-46-3 CYTIDINE 
• 2382-64-1 CpU 
• 2536-99-4 cytidylyl-(3'->5')-cytidine 

Downstream Products

• 2536-99-4 [3']cytidylic acid cytidin-5'-yl ester 
• 2382-66-3 Cytidin-(3',5')-adenosin 
• 84-52-6 cytidine 3'-monophosphate 
• 85-94-9 cytidine-2'-monophosphate 
• 65-46-3 CYTIDINE 

Relevant articles and documents

Prebiotically Plausible RNA Activation Compatible with Ribozyme-Catalyzed Ligation

RNA-catalyzed RNA ligation is widely believed to be a key reaction for primordial biology. However, since typical chemical routes towards activating RNA substrates are incompatible with ribozyme catalysis, it remains unclear how prebiotic systems generated and sustained pools of activated building blocks needed to form increasingly larger and complex RNA. Herein, we demonstrate in situ activation of RNA substrates under reaction conditions amenable to catalysis by the hairpin ribozyme. We found that diamidophosphate (DAP) and imidazole drive the formation of 2′,3′-cyclic phosphate RNA mono- and oligonucleotides from monophosphorylated precursors in frozen water-ice. This long-lived activation enables iterative enzymatic assembly of long RNAs. Our results provide a plausible scenario for the generation of higher-energy substrates required to fuel ribozyme-catalyzed RNA synthesis in the absence of a highly evolved metabolism.

Guanidine based self-assembled monolayers on Au nanoparticles as artificial phosphodiesterases

Gold nanoparticles passivated with a long chain alkanethiol decorated with a phenoxyguanidine moiety were prepared and investigated as catalysts in the cleavage of the RNA model compound HPNP and diribonucleoside monophosphates. The catalytic efficiency and the high effective molarity value of the Au monolayer protected colloids points to a high level of cooperation between the catalytic groups.

Expeditious, potentially primordial, aminoacylation of nucleotides

(Chemical Equation Presented) In the beginning: Mixed carboxylic phosphoric anhydrides 3, formed from 3′-nucleotides 1 and amino acid N-carboxyanhydrides 2, undergo competing rearrangement to 2′-aminoacyl esters 4 and cyclization to 2′,3′-cyclic phosphates 5. The intramolecular aminoacyl transfer is faster than the cyclization despite the ease with which 2′,3′-cyclic phosphates are formed through any other form of phosphate activation.