SML1228

Cyclic-di-GMP sodium salt

≥98% (HPLC), powder, quorum sensing molecule

• Synonym(s): 3′,5′-Cyclic diguanylic acid sodium salt, Bis(3′,5′)-cyclic diguanylic acid sodium salt, Cyclic Diguanosine-5′-monophosphate sodium salt, c-di-GMP sodium salt, c-diGMP sodium salt, cGpGp sodium salt
• Empirical Formula (Hill Notation): C₂₀H₂₄N₁₀O₁₄P₂ · xNa⁺
• CAS Number: 61093-23-0
• Molecular Weight: 690.41 (free acid basis)
• UNSPSC Code: 12352200
• PubChem Substance ID: 329825732
• NACRES: NA.77

Properties

• product name: Cyclic-di-GMP sodium salt, ≥98% (HPLC)
• description: contains 1μmol of powder (approx. 0.7mg)
• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• storage temp.: −20°C
• SMILES string: O[C@@H]1[C@H](OP(OC[C@H]2O[C@@H](N3C(N=C(N)NC4=O)=C4N=C3)[C@H](O)[C@@H]2O5)(O)=O)[C@@H](COP5(O)=O)O[C@H]1N6C(N=C(N)NC7=O)=C7N=C6.C
• InChI: 1S/C20H24N10O14P2/c21-19-25-13-7(15(33)27-19)23-3-29(13)17-9(31)11-5(41-17)1-39-45(35,36)44-12-6(2-40-46(37,38)43-11)42-18(10(12)32)30-4-24-8-14(30)26-20(22)28-16(8)34/h3-6,9-12,17-18,31-32H,1-2H2,(H,35,36)(H,37,38)(H3,21,25,27,33)(H3,22,26,28,34)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1
• InChI key: PKFDLKSEZWEFGL-MHARETSRSA-N

Description

Application

Cyclic-di-GMP sodium salt has been used as a quorum sensing molecule.

Biochem/physiol Actions

Cyclic-di-GMP is a naturally occurring small molecule that acts as a bacterial second messenger to regulate important signaling mechanisms in prokaryotes that control bacterial survival, adhesion, colonization, biofilm formation, and virulence factors production. During infections Cyclic-di-GMP is bound by host STING (stimulator of interferon genes) leading to expression of interferon genes, activating innate immune responses. c-di-GMP has been found in eukarotic systems acting not only in immune response, but as an inhibitor of the pacemaker I(f) current in the heart.

Preparation Note

Cyclic-di-GMP is soluble in water and aqueous buffers.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable