2382-65-2

Basic information

• Product Name: CYTIDYLYL-(3'->5')-GUANOSINE
• Synonyms: CYTIDYLYL-(3'->5')-GUANOSINE;CPG;3'-Cytidylic acid 5'-guanosyl ester;5'-Guanylic acid 3'-cytidyl ester;5'-O-(3'-Cytidylyl)guanosine;Dinucleotide CpG;[(2R,3S,4R,5R)-5-(2-amino-6-keto-3H-purin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl [(2R,3S,4R,5R)-5-(4-amino-2-keto-pyrimidin-1-yl)-4-hydroxy-2-methylol-tetrahydrofuran-3-yl] hydrogen phosphate;[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate
• CAS NO: 2382-65-2
• Molecular Formula: C₁₉H₂₅N₈O₁₂P
• Molecular Weight: 588.42
• EINECS: 219-186-1
• Mol File: 2382-65-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 1057.6°Cat760mmHg
• Flash Point: 593.4°C
• Appearance: /
• Density: 0.4 g/mL at 20 °C(lit.)
• CAS DataBase Reference: CYTIDYLYL-(3'->5')-GUANOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: CYTIDYLYL-(3'->5')-GUANOSINE(2382-65-2)
• EPA Substance Registry System: CYTIDYLYL-(3'->5')-GUANOSINE(2382-65-2)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 2382-65-2(Hazardous Substances Data)

Usage

General Description

CYTIDYLYL-(3'->5')-GUANOSINE, also known as C-GMP, is a dinucleotide molecule made up of the nucleosides cytidine and guanosine joined by a phosphodiester bond. It plays important roles in various biological processes, including signaling pathways and cellular communication. C-GMP is a key component of various signaling pathways in the body, including those involved in the regulation of blood pressure, smooth muscle relaxation, and neurotransmission. It is also involved in the regulation of cell growth, differentiation, and apoptosis. Additionally, C-GMP is a key component of the cGMP-dependent protein kinase (PKG) signaling pathway, which plays important roles in regulating various physiological functions within the body. Its structure and function make C-GMP an essential molecule for maintaining cellular homeostasis and proper functioning of the body.

Upstream product

• 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 

Downstream Products

• 633-90-9 cytidine 2',3'-cyclic monophosphate 
• 84-52-6 cytidine 3'-monophosphate 
• 85-94-9 cytidine-2'-monophosphate 
• 118-00-3 G 

Relevant articles and documents

Kinetic analysis of the cleavage of the ribose phosphodiester bond within guanine and cytosine-rich oligonucleotides and dinucleotides at 65-200 °C and its implications concerning the chemical evolution of RNA

A monitoring method of rapid hydrothermal reactions was successfully applied to a kinetic analysis of the cleavage of a ribose phosphodiester bond within oligonucleotides and dinucleotides at 150-200 °C. The apparent rate constants (kapp) of degradation of the ribose 3′,5′-cytidylylguanosine sequence (-C3′pGd-) within oligonucleotides and dinucleotides were determined, where the -C3′pGd- sequence in oligonucleotides is less stable than 2′,5′-cytidylylguanosine (C2′pG) and 3′,5′-cytidylylguanosine (C3′pG). It was unexpected that the stability of the target sequence would be dependent on the surrounding sequences of the oligonucleotides, although the temperatures used in the study were extremely higher than the melting points. The stability of a phosphodiester bond of 2′-deoxycytidylyl-2′-deoxyguanosine (CdpGd) is much higher than that of a ribose phosphodiester bond at low temperatures, but becomes comparable at 200 °C. During the degradation of C2′pG or C3′pG, interconversion between C2′pG and C3′pG was observed along with cleavage of the phosphodiester bond. Based on an analysis of the extent of interconversion, the apparent rate constants of the disappearance of C2′pG and C3′pG were dissected into the rate constants of hydrolysis (khy) and interconversion (kint), where the values of khy were greater than those of kint. The apparent activation energy of the degradation of the target sequence was 100-109 kJ mol-1 for oligonucleotides, 90 kJ mol-1 for C3′pG, and 87 kJ mol-1 for C2′pG, and 139 kJ mol-1 for CdpGd. The apparent activation enthalpy and entropy changes of the degradation of the target sequence were also determined; the values of the activation parameter were ΔHapp = 94-105 kJ mol-1 and ΔSapp= -(36-59) J mol-1 T-1 for five oligonucleotides, ΔHapp = 86 kJ mol-1 and ΔSapp = -97 J mol-1 T-1 for C3′pG, ΔHapp = 84 kJ mol-1, ΔXSapp = - 105 J mol-1 T-1 for C2′pG, and ΔHapp = 135 kJ mol-1, ΔSapp = +2 J mol-1 T-1 for CdpGd. The activation parameters, ΔHapp and ΔSapp, for the oligonucleotides increased with the length of the surrounding sequence of -C3′pGd-; this fact clearly demonstrates the existence of the influence of the surrounding sequence for the stability of the target ribose phosphodiester bond. Based on a kinetic analysis, the reaction mechanism of the degradation of the ribose phosphodiester bond at high temperatures is discussed. Furthermore, possible pathways of the chemical evolution of RNA are discussed from the viewpoint of the hydrothermal origin of life.