Key Documents

View All Documentation

SML1228

Cyclic-di-GMP sodium salt

Name: Cyclic-di-GMP sodium salt
Brand: SIGMA

≥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

Select a Size

Change View

About This Item

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

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Transcriptional and Mycolic Acid Profiling in Mycobacterium bovis BCG In Vitro Show an Effect for c-di-GMP and Overlap between Dormancy and Biofilms.

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

An Aphrodisiac Produced By Vibrio fischeri Stimulates Mating In The Closest Living Relatives Of Animals.

Woznica A, et al.

bioRxiv, 139022-139022 (2017)

Mass spectrometric characterization of cyclic dinucleotides (CDNs) in vivo.

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

View All Related Papers