CAS 1441190-66-4

2′-Guanylic acid, adenylyl-(3′→5′)-, cyclic nucleotide

Description:

2′-Guanylic acid, adenylyl-(3′→5′)-, cyclic nucleotide, commonly referred to as cyclic guanosine monophosphate (cGMP), is a crucial signaling molecule in various biological processes. It is a cyclic nucleotide formed from guanosine triphosphate (GTP) and plays a significant role in cellular signaling pathways, particularly in the regulation of vascular smooth muscle relaxation and neurotransmission. cGMP acts as a secondary messenger, mediating the effects of nitric oxide and influencing various physiological functions, including blood pressure regulation and neuronal signaling. The cyclic structure of cGMP allows it to interact with specific protein targets, such as protein kinases and phosphodiesterases, thereby modulating their activity. Additionally, cGMP is involved in the regulation of ion channels and gene expression. Its levels are tightly regulated within cells, as they can be rapidly synthesized and degraded, ensuring precise control over its signaling functions. Overall, cGMP is integral to numerous physiological processes and is a key player in the signaling pathways of many organisms.

Formula: C₂₀H₂₄N₁₀O₁₃P₂

InChI: InChI=1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)18-11(32)12-7(41-18)2-39-45(36,37)43-13-10(31)6(1-38-44(34,35)42-12)40-19(13)30-5-26-9-16(30)27-20(22)28-17(9)33/h3-7,10-13,18-19,31-32H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H3,22,27,28,33)/t6?,7-,10-,11-,12-,13-,18-,19-/m1/s1

InChI key: InChIKey=XRILCFTWUCUKJR-RVJIVEKKSA-N

SMILES: O[C@H]1[C@@]2([C@@H](O[C@]1(COP(=O)(O)O[C@@]3([C@@](COP(=O)(O)O2)(O[C@H]([C@@H]3O)N4C=5C(N=C4)=C(N)N=CN5)[H])[H])[H])N6C7=C(N=C6)C(=O)N=C(N)N7)[H]

Synonyms:

• 2′-Guanylic acid, adenylyl-(3′→5′)-, cyclic nucleotide
• cGAMP(2′→5′)
• 2′,3′-Cyclic guanosine monophosphate-adenosine monophosphate
• Cyclic Gp(2′→5′)Ap(3′→5′)
• 2′-3′-cyclic GMP-AMP
• Mammalian (non-canonical) CDN
• c[G(2',5')pA(3',5')p] / 2'3'-cGAMP
• 5’)pA(3’
• MAMMALIAN (NON-CANONICAL) CDN; CYCLIC [G(2';5')PA(3';5')P]
• 2'3'-cGAMP
• 2',3'-cGAMP (free acid)
• 2′,3′-Cyclic guanosine adenosine monophosphate
• cyclic [G(2’

Adenylyl-(3′→5′)-2′-guanylic acid, cyclic nucleotide

CAS: 1441190-66-4

Formula: C₂₀H₂₄N₁₀O₁₃P₂

Purity: 98%

Color and Shape: Solid

Molecular weight: 674.4113

Ref: IN-DA01E6PX

2',3'-cGAMP

CAS: 1441190-66-4

2',3'-cGAMP is an endogenous cyclic dinucleotide (CDN) produced by cGAS (cGAMP synthase). a STING activator and ligand.

Formula: C₂₀H₂₄N₁₀O₁₃P₂

Color and Shape: Solid

Molecular weight: 674.41

Ref: TM-T10065

2’3’-cGAMP Sodium Salt

Controlled Product

CAS: 1441190-66-4

Formula: C₂₀H₂₂N₁₀Na₂O₁₃P₂

Color and Shape: Neat

Molecular weight: 718.375

Ref: TR-G368910

Cyclic Guanosine-(2',5')-monophosphate-adenosine-(3'',5'')-monophosphate Di-ammonium Salt

Controlled Product

CAS: 1441190-66-4

Applications Cyclic Guanosine-(2',5')-monophosphate-adenosine-(3'',5'')-monophosphate Di-ammonium Salt is a non-symmetrical, mixed phosphodiester link dimeric nucleotide. It is a natural substrate for the immune adaptor protein STING.
References Wang, J., et al.: Journal of Investigative Dermatology, 136, 2183-2191 (2016); Chem. and Eng. News page 24 Feb. 26, 2018

Formula: C₂₀H₂₂N₁₀O₁₃P₂•2(NH₄)

Color and Shape: Neat

Molecular weight: 690.11868

Ref: TR-C990140

2',3'-Cyclic guanosine monophosphate-adenosine monophosphate

CAS: 1441190-66-4

cyclic guanosine monophosphate (cGMP) is increasingly recognized as having widespread consequences for human health which include regulation of biofilm formation as well as virulence.  It has now been identified as a specific and high affinity ligand for the GEMM class of bacterial riboswitches that regulate gene expression.

Formula: C₂₀H₂₄N₁₀O₁₃P₂

Purity: Min. 95%

Molecular weight: 674.41 g/mol

Ref: 3D-NC159040