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Merck

SML1228

Cyclic-di-GMP sodium salt

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

Synonyme(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

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A propos de cet article

Formule empirique (notation de Hill) :
C20H24N10O14P2 · xNa+
Numéro CAS:
61093-23-0
Poids moléculaire :
690.41 (free acid basis)
UNSPSC Code:
12352200
PubChem Substance ID:
329825732
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

Principaux documents

Voir toute la documentation
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Nom du produit

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

Catégories apparentées

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.
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.

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000465506
0000469105
0000469105
0000465506
0000247005

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

An Aphrodisiac Produced By Vibrio fischeri Stimulates Mating In The Closest Living Relatives Of Animals.
Woznica A, et al.
bioRxiv, 139022-139022 (2017)
Miguel Angel De la Cruz-Villegas et al.
Journal of microbiology and biotechnology, 30(6), 811-821 (2020-04-03)
Mycobacterium tuberculosis produces mycolic acids which are relevant for persistence, recalcitrance to antibiotics and defiance to host immunity. c-di-GMP is a second messenger involved in transition from planktonic cells to biofilms, whose levels are controlled by diguanylate cyclases (DGC) and
Andrea Annibal et al.
Analytical and bioanalytical chemistry, 413(26), 6457-6468 (2021-09-04)
Cyclic dinucleotides (CDNs) are key secondary messenger molecules produced by cyclic dinucleotide synthases that trigger various cellular signaling cascades from bacteria to vertebrates. In mammals, cyclic GMP-AMP synthase (cGAS) has been shown to bind to intracellular DNA and catalyze the
Lei Zhang et al.
Nature communications, 11(1), 5371-5371 (2020-10-25)
Autoinducer-2 (AI-2) is a quorum sensing signal that mediates communication within and between many bacterial species. However, its known receptors (LuxP and LsrB families) are not found in all the bacteria capable of responding to this signaling molecule. Here, we
Emily N Chin et al.
Science (New York, N.Y.), 369(6506), 993-999 (2020-08-21)
Stimulator of interferon genes (STING) links innate immunity to biological processes ranging from antitumor immunity to microbiome homeostasis. Mechanistic understanding of the anticancer potential for STING receptor activation is currently limited by metabolic instability of the natural cyclic dinucleotide (CDN)
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