c-di-AMP | 54447-84-6 | Second messenger

MedKoo Cat#: 208112 | Name: c-di-AMP

Description:

WARNING: This product is for research use only, not for human or veterinary use.

c-di-AMP is a second messenger that maintains cell viability, homeostasis, and pathogenicity.

Chemical Structure

c-di-AMP

CAS#54447-84-6 (free acid)

Theoretical Analysis

MedKoo Cat#: 208112

Name: c-di-AMP

CAS#: 54447-84-6 (free acid)

Chemical Formula: C20H24N10O12P2

Exact Mass: 658.1050

Molecular Weight: 658.42

Elemental Analysis: C, 36.48; H, 3.67; N, 21.27; O, 29.16; P, 9.41

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

2734909-87-4 (sodium) 54447-84-6 (free acid)

Synonym

c-di-AMP; c di AMP; c-diAMP; cdi-AMP

IUPAC/Chemical Name

(2R,3R,3aS,7aR,9R,10R,10aS,14aR)-2,9-bis(6-amino-9H-purin-9-yl)-3,5,10,12-tetrahydroxyoctahydro-2H,7H-difuro[3,2-d:3',2'-j][1,3,7,9]tetraoxa[2,8]diphosphacyclododecine 5,12-dioxide

InChi Key

PDXMFTWFFKBFIN-XPWFQUROSA-N

InChi Code

InChI=1S/C20H24N10O12P2/c21-15-9-17(25-3-23-15)29(5-27-9)19-11(31)13-7(39-19)1-37-43(33,34)42-14-8(2-38-44(35,36)41-13)40-20(12(14)32)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-32H,1-2H2,(H,33,34)(H,35,36)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1

SMILES Code

NC1=C(N=CN2[C@H]3[C@H](O)[C@H](OP(OC[C@H]4O[C@@H](N5C(N=CN=C6N)=C6N=C5)[C@H](O)[C@@H]4OP(O)(OC7)=O)(O)=O)[C@@H]7O3)C2=NC=N1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 658.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Wang M, Wamp S, Gibhardt J, Holland G, Schwedt I, Schmidtke KU, Scheibner K, Halbedel S, Commichau FM. Adaptation of Listeria monocytogenes to perturbation of c-di-AMP metabolism underpins its role in osmoadaptation and identifies a fosfomycin uptake system. Environ Microbiol. 2022 Jun 10. doi: 10.1111/1462-2920.16084. Epub ahead of print. PMID: 35688634. 2: Ning H, Liang X, Xie Y, Bai L, Zhang W, Wang L, Kang J, Lu Y, Ma Y, Bai G, Bai Y. c-di-AMP Accumulation Regulates Growth, Metabolism, and Immunogenicity of Mycobacterium smegmatis. Front Microbiol. 2022 May 24;13:865045. doi: 10.3389/fmicb.2022.865045. PMID: 35685938; PMCID: PMC9171234. 3: Lowry RC, Hallberg ZF, Till R, Simons TJ, Nottingham R, Want F, Sockett RE, Hammond MC, Lambert C. Production of 3',3'-cGAMP by a Bdellovibrio bacteriovorus promiscuous GGDEF enzyme, Bd0367, regulates exit from prey by gliding motility. PLoS Genet. 2022 May 27;18(5):e1010164. doi: 10.1371/journal.pgen.1010164. PMID: 35622882; PMCID: PMC9140294. 4: Tang Q, Precit MR, Thomason MK, Blanc SF, Ahmed-Qadri F, McFarland AP, Wolter DJ, Hoffman LR, Woodward JJ. Thymidine starvation promotes c-di-AMP-dependent inflammation during pathogenic bacterial infection. Cell Host Microbe. 2022 Apr 12:S1931-3128(22)00158-5. doi: 10.1016/j.chom.2022.03.028. Epub ahead of print. PMID: 35439435. 5: Temizoz B, Hioki K, Kobari S, Jounai N, Kusakabe T, Lee MSJ, Coban C, Kuroda E, Ishii KJ. Anti-tumor immunity by transcriptional synergy between TLR9 and STING activation. Int Immunol. 2022 Apr 14:dxac012. doi: 10.1093/intimm/dxac012. Epub ahead of print. PMID: 35419609. 6: Cabezas A, Costas MJ, Canales J, Pinto RM, Rodrigues JR, Ribeiro JM, Cameselle JC. Enzyme Characterization of Pro-virulent SntA, a Cell Wall-Anchored Protein of Streptococcus suis, With Phosphodiesterase Activity on cyclic- di-AMP at a Level Suited to Limit the Innate Immune System. Front Microbiol. 2022 Mar 22;13:843068. doi: 10.3389/fmicb.2022.843068. PMID: 35391727; PMCID: PMC8981391. 7: Li H, Li T, Zou W, Ni M, Hu Q, Qiu X, Yao Z, Fan J, Li L, Huang Q, Zhou R. IPA-3: An Inhibitor of Diadenylate Cyclase of Streptococcus suis with Potent Antimicrobial Activity. Antibiotics (Basel). 2022 Mar 21;11(3):418. doi: 10.3390/antibiotics11030418. PMID: 35326881; PMCID: PMC8944544. 8: Mantovani O, Reimann V, Haffner M, Herrmann FP, Selim KA, Forchhammer K, Hess WR, Hagemann M. The impact of the cyanobacterial carbon-regulator protein SbtB and of the second messengers cAMP and c-di-AMP on CO2 -dependent gene expression. New Phytol. 2022 Jun;234(5):1801-1816. doi: 10.1111/nph.18094. Epub 2022 Apr 9. PMID: 35285042. 9: Pérez I, Campos-Pardos E, Díaz C, Uranga S, Sayes F, Vicente F, Aguiló N, Brosch R, Martín C, Gonzalo-Asensio J. The Mycobacterium tuberculosis PhoPR virulence system regulates expression of the universal second messenger c-di-AMP and impacts vaccine safety and efficacy. Mol Ther Nucleic Acids. 2022 Feb 15;27:1235-1248. doi: 10.1016/j.omtn.2022.02.011. PMID: 35282413; PMCID: PMC8894143. 10: Pacini MF, González FB, Dinatale B, Bulfoni Balbi C, Villar SR, Farré C, Lupi G, Espariz M, Blancato VS, Magni C, Marcipar I, Pérez AR. Nasal immunization with a L. lactis-derived trans-sialidase antigen plus c-di-AMP protects against acute oral T. cruzi infection. Vaccine. 2022 Apr 1;40(15):2311-2323. doi: 10.1016/j.vaccine.2022.02.071. Epub 2022 Mar 9. PMID: 35279330. 11: Singh AK, Praharaj M, Lombardo KA, Yoshida T, Matoso A, Baras AS, Zhao L, Srikrishna G, Huang J, Prasad P, Powell JD, Kates M, McConkey D, Pardoll DM, Bishai WR, Bivalacqua TJ. Re-engineered BCG overexpressing cyclic di-AMP augments trained immunity and exhibits improved efficacy against bladder cancer. Nat Commun. 2022 Feb 15;13(1):878. doi: 10.1038/s41467-022-28509-z. PMID: 35169141; PMCID: PMC8847416. 12: Wendel BM, Pi H, Krüger L, Herzberg C, Stülke J, Helmann JD. A Central Role for Magnesium Homeostasis during Adaptation to Osmotic Stress. mBio. 2022 Feb 15;13(1):e0009222. doi: 10.1128/mbio.00092-22. Epub ahead of print. PMID: 35164567; PMCID: PMC8844918. 13: Krüger L, Herzberg C, Wicke D, Scholz P, Schmitt K, Turdiev A, Lee VT, Ischebeck T, Stülke J. Sustained Control of Pyruvate Carboxylase by the Essential Second Messenger Cyclic di-AMP in Bacillus subtilis. mBio. 2022 Feb 8;13(1):e0360221. doi: 10.1128/mbio.03602-21. Epub ahead of print. PMID: 35130724; PMCID: PMC8822347. 14: Onyedibe KI, Elmanfi S, Aryal UK, Könönen E, Gürsoy UK, Sintim HO. Global proteomics of fibroblast cells treated with bacterial cyclic dinucleotides, c-di-GMP and c-di-AMP. J Oral Microbiol. 2021 Dec 29;14(1):2003617. doi: 10.1080/20002297.2021.2003617. PMID: 34992733; PMCID: PMC8725719. 15: Mahto KU, Kumari S, Das S. Unraveling the complex regulatory networks in biofilm formation in bacteria and relevance of biofilms in environmental remediation. Crit Rev Biochem Mol Biol. 2022 Jun;57(3):305-332. doi: 10.1080/10409238.2021.2015747. Epub 2021 Dec 22. PMID: 34937434. 16: Galperin MY, Chou SH. Sequence Conservation, Domain Architectures, and Phylogenetic Distribution of the HD-GYP Type c-di-GMP Phosphodiesterases. J Bacteriol. 2022 Apr 19;204(4):e0056121. doi: 10.1128/jb.00561-21. Epub 2021 Dec 20. PMID: 34928179; PMCID: PMC9017333. 17: Braun F, Recalde A, Bähre H, Seifert R, Albers SV. Putative Nucleotide-Based Second Messengers in the Archaeal Model Organisms Haloferax volcanii and Sulfolobus acidocaldarius. Front Microbiol. 2021 Nov 22;12:779012. doi: 10.3389/fmicb.2021.779012. PMID: 34880846; PMCID: PMC8646023. 18: Torres R, Alonso JC. Bacillus subtilis RecA, DisA, and RadA/Sms Interplay Prevents Replication Stress by Regulating Fork Remodeling. Front Microbiol. 2021 Nov 22;12:766897. doi: 10.3389/fmicb.2021.766897. PMID: 34880841; PMCID: PMC8645862. 19: Selim KA, Haffner M, Burkhardt M, Mantovani O, Neumann N, Albrecht R, Seifert R, Krüger L, Stülke J, Hartmann MD, Hagemann M, Forchhammer K. Diurnal metabolic control in cyanobacteria requires perception of second messenger signaling molecule c-di-AMP by the carbon control protein SbtB. Sci Adv. 2021 Dec 10;7(50):eabk0568. doi: 10.1126/sciadv.abk0568. Epub 2021 Dec 8. PMID: 34878830; PMCID: PMC8654305. 20: Gándara C, Torres R, Carrasco B, Ayora S, Alonso JC. DisA Restrains the Processing and Cleavage of Reversed Replication Forks by the RuvAB-RecU Resolvasome. Int J Mol Sci. 2021 Oct 20;22(21):11323. doi: 10.3390/ijms222111323. PMID: 34768753; PMCID: PMC8583203.