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54447-84-6
Catalog No.:AA00D9VI

54447-84-6 | C-di-amp

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1mg
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00D9VI
Chemical Name:
C-di-amp
CAS Number:
54447-84-6
Molecular Formula:
C20H24N10O12P2
Molecular Weight:
658.4119
SMILES:
O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]3O[C@H]([C@@H]([C@@H]3OP(=O)(OC[C@H]2O[C@H]1n1cnc2c1ncnc2N)O)O)n1cnc2c1ncnc2N
Properties
Computed Properties
 
Complexity:
1080  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
8  
Heavy Atom Count:
44  
Hydrogen Bond Acceptor Count:
20  
Hydrogen Bond Donor Count:
6  
Rotatable Bond Count:
2  
XLogP3:
-5.1  

Literature

Title: Mycobacterium tuberculosis Rv3586 (DacA) is a diadenylate cyclase that converts ATP or ADP into c-di-AMP.

Journal: PloS one 20120101

Title: c-di-AMP is a new second messenger in Staphylococcus aureus with a role in controlling cell size and envelope stress.

Journal: PLoS pathogens 20110901

Title: Bis-(3',5')-cyclic dimeric adenosine monophosphate: strong Th1/Th2/Th17 promoting mucosal adjuvant.

Journal: Vaccine 20110718

Title: c-di-AMP reports DNA integrity during sporulation in Bacillus subtilis.

Journal: EMBO reports 20110601

Title: Identification of a Streptococcus pyogenes SF370 gene involved in production of c-di-AMP.

Journal: Nagoya journal of medical science 20110201

Title: c-di-AMP secreted by intracellular Listeria monocytogenes activates a host type I interferon response.

Journal: Science (New York, N.Y.) 20100625

Title: YybT is a signaling protein that contains a cyclic dinucleotide phosphodiesterase domain and a GGDEF domain with ATPase activity.

Journal: The Journal of biological chemistry 20100101

Title: Structural basis of ligand binding by a c-di-GMP riboswitch.

Journal: Nature structural & molecular biology 20091201

Title: Great times for small molecules: c-di-AMP, a second messenger candidate in Bacteria and Archaea.

Journal: Science signaling 20080819

Title: Structural biochemistry of a bacterial checkpoint protein reveals diadenylate cyclase activity regulated by DNA recombination intermediates.

Journal: Molecular cell 20080425

Title: Fahmi T, et al. c-di-AMP: An Essential Molecule in the Signaling Pathways that Regulate the Viability and Virulenceof Gram-Positive Bacteria. Genes (Basel). 2017 Aug 7;8(8).

Title: Ning H, et al. Recombinant BCG With Bacterial Signaling Molecule Cyclic di-AMP as Endogenous AdjuvantInduces Elevated Immune Responses After Mycobacterium tuberculosis Infection. Front Immunol. 2019 Jul 3;10:1519.

Title: Ebensen T, et al. The Combination Vaccine Adjuvant System Alum/c-di-AMP Results in Quantitative and QualitativeEnhanced Immune Responses Post Immunization. Front Cell Infect Microbiol. 2019 Feb 19;9:31.

Title: Sanchez MV, et al. Intranasal delivery of influenza rNP adjuvanted with c-di-AMP induces strong humoral and cellularimmune responses and provides protection against virus challenge. PLoS One. 2014 Aug 20;9(8):e104824.

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