1904-98-9 | 2,6-Diaminopurine

Packsize	Purity	Availability	Price	Discounted Price
5g	97%	in stock	$13.00	$9.00
10g	97%	in stock	$26.00	$18.00
25g	97%	in stock	$48.00	$33.00
100g	97%	in stock	$129.00	$90.00
500g	97%	in stock	$580.00	$406.00

Description

• Catalog Number: AB11965
• Chemical Name: 2,6-Diaminopurine
• CAS Number: 1904-98-9
• Molecular Formula: C5H6N6
• Molecular Weight: 150.1413
• MDL Number: MFCD00047146
• SMILES: Nc1nc(N)c2c(n1)[nH]cn2
• NSC Number: 743

Computed Properties

• Complexity: 150
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 11
• Hydrogen Bond Acceptor Count: 5
• Hydrogen Bond Donor Count: 3
• XLogP3: -0.9

Upstream Synthesis Route

2,6-Diaminopurine, also known as DAP, is a compound with significant applications in chemical synthesis. Its unique molecular structure and properties make it a valuable building block in the creation of various chemical compounds.One of the key applications of 2,6-Diaminopurine in chemical synthesis is its use as a precursor for the synthesis of nucleoside analogs. Nucleoside analogs are essential in medicinal chemistry for developing antiviral and anticancer drugs. By incorporating 2,6-Diaminopurine into nucleoside analogs, researchers can tailor the compounds for specific biological targets, enhancing their pharmacological properties and efficacy.Furthermore, 2,6-Diaminopurine serves as a versatile starting material for the preparation of various heterocyclic compounds. Its ability to participate in a range of chemical reactions allows for the synthesis of complex molecules with diverse functionalities. This makes 2,6-Diaminopurine a valuable tool for organic chemists seeking to design novel compounds for pharmaceutical, agrochemical, and material science applications.In summary, the application of 2,6-Diaminopurine in chemical synthesis is multifaceted, offering researchers a powerful tool for the efficient and precise construction of diverse chemical structures with important implications for drug discovery and materials science.

Literature

• Structural context effects in the oxidation of 8-oxo-7,8-dihydro-2'-deoxyguanosine to hydantoin products: electrostatics, base stacking, and base pairing.

  Journal of the American Chemical Society 20120912

• Simulations of A-RNA duplexes. The effect of sequence, solute force field, water model, and salt concentration.

  The journal of physical chemistry. B 20120823

• Synthesis and antiviral activity of certain second generation methylenecyclopropane nucleosides.

  Bioorganic & medicinal chemistry 20120615

• Long lifetime of hydrogen-bonded DNA basepairs by force spectroscopy.

  Biophysical journal 20120516

• Synthesis and oligomerization of Fmoc/Boc-protected PNA monomers of 2,6-diaminopurine, 2-aminopurine and thymine.

  Organic & biomolecular chemistry 20120128

• The 3' splice site of influenza A segment 7 mRNA can exist in two conformations: a pseudoknot and a hairpin.

  PloS one 20120101

• Biotransformation of 2,6-diaminopurine nucleosides by immobilized Geobacillus stearothermophilus.

  Biotechnology progress 20120101

• Enhanced topical and transdermal delivery of antineoplastic and antiviral acyclic nucleoside phosphonate cPr-PMEDAP.

  Pharmaceutical research 20111201

• Weak seed-pairing stability and high target-site abundance decrease the proficiency of lsy-6 and other microRNAs.

  Nature structural & molecular biology 20111001

• Di-μ-but-2-enoato-bis-[diaqua-bis(but-2-enoato)neodymium(III)] 2,6-diamino-purine disolvate.

  Acta crystallographica. Section E, Structure reports online 20110901

• Pa0148 from Pseudomonas aeruginosa catalyzes the deamination of adenine.

  Biochemistry 20110802

• Tetraaquabis(2,6-diamine-7H-purine-κN9)cobalt(II) benzene-1,2,4,5-tetracarboxylate tetrahydrate.

  Acta crystallographica. Section C, Crystal structure communications 20110801

• Role of the heat capacity change in understanding and modeling melting thermodynamics of complementary duplexes containing standard and nucleobase-modified LNA.

  Biochemistry 20110614

• ATP and its N⁶-substituted analogues: parameterization, molecular dynamics simulation and conformational analysis.

  Journal of molecular modeling 20110501

• Two isomorphous transition metal complexes containing a protonated diaminopurine ligand: diaquabis(2,6-diamino-7H-purin-1-ium-κN9)bis(homophthalato-κO)nickel(II) tetrahydrate and the cobalt(II) analogue.

  Acta crystallographica. Section C, Crystal structure communications 20110501

• Synthesis and antiviral activity of N9-[3-fluoro-2-(phosphonomethoxy)propyl] analogues derived from N6-substituted adenines and 2,6-diaminopurines.

  Bioorganic & medicinal chemistry 20110401

• Novel ligands for a purine riboswitch discovered by RNA-ligand docking.

  Chemistry & biology 20110325

• Bis(2,6-diamino-1H-purin-3-ium) di-μ-croconato-κ3O,O':O'';κ3O:O',O''-bis[tetraaqua(croconato-κ2O,O')neodymium(III)].

  Acta crystallographica. Section C, Crystal structure communications 20110101

• Comparative study between transcriptionally- and translationally-acting adenine riboswitches reveals key differences in riboswitch regulatory mechanisms.

  PLoS genetics 20110101

• An update on targeted gene repair in mammalian cells: methods and mechanisms.

  Journal of biomedical science 20110101

• Study of camelpox virus pathogenesis in athymic nude mice.

  PloS one 20110101

• Enzymatic synthesis of nucleosides by nucleoside phosphorylase co-expressed in Escherichia coli.

  Journal of Zhejiang University. Science. B 20101101

• 2,6-Diamino-9H-purine monohydrate and bis(2,6-diamino-9H-purin-1-ium) 2-(2-carboxylatophenyl)acetate heptahydrate: two simple structures with very complex hydrogen-bonding schemes.

  Acta crystallographica. Section C, Crystal structure communications 20101101

• Computational mutagenesis studies of hammerhead ribozyme catalysis.

  Journal of the American Chemical Society 20100929

• Comparisons between chemical mapping and binding to isoenergetic oligonucleotide microarrays reveal unexpected patterns of binding to the Bacillus subtilis RNase P RNA specificity domain.

  Biochemistry 20100921

• Identification of small molecule compounds with higher binding affinity to guanine deaminase (cypin) than guanine.

  Bioorganic & medicinal chemistry 20100915

• Antiviral treatment of chronic hepatitis B virus (HBV) infections.

  Viruses 20100601

• Role of the adenine ligand on the stabilization of the secondary and tertiary interactions in the adenine riboswitch.

  Journal of molecular biology 20100312

• Preparation of the 2'-deoxynucleosides of 2,6-diaminopurine and isoguanine by direct glycosylation.

  The Journal of organic chemistry 20100305

• Multivector fluorescence analysis of the xpt guanine riboswitch aptamer domain and the conformational role of guanine.

  Biochemistry 20100302

• Characterization of plant sulfiredoxin and role of sulphinic form of 2-Cys peroxiredoxin.

  Journal of experimental botany 20100301

• Long-range charge transfer through DNA by replacing adenine with diaminopurine.

  Journal of the American Chemical Society 20100120

• Inhibition of human immunodeficiency virus type-1 by cdk inhibitors.

  AIDS research and therapy 20100101

• Effect of substituents on the excited-state dynamics of the modified DNA bases 2,4-diaminopyrimidine and 2,6-diaminopurine.

  Physical chemistry chemical physics : PCCP 20100101

• Reactions of Pd(II) with chelate-tethered 2,6-diaminopurine derivatives: N3-coordination and reaction of the purine system.

  Inorganic chemistry 20091207

• Probing metal-ion purine interactions at DNA minor-groove sites.

  Inorganic chemistry 20091102

• Two isomorphous crotonatolanthanide complexes: tetra-mu-but-2-enoato-bis[diaqua(but-2-enoato)Ln]-2,6-diaminopurine (1/2) (Ln = Dy and Ho).

  Acta crystallographica. Section C, Crystal structure communications 20091101

• Co-expression of recombinant nucleoside phosphorylase from Escherichia coli and its application.

  Applied biochemistry and biotechnology 20091001

• Marine-derived metabolites of S-adenosylmethionine as templates for new anti-infectives.

  Marine drugs 20090901

• Kinetic analysis of base-pairing preference for nucleotide incorporation opposite template pyrimidines by human DNA polymerase iota.

  Journal of molecular biology 20090605

• Monitoring RNA-ligand interactions using isothermal titration calorimetry.

  Methods in molecular biology (Clifton, N.J.) 20090101

• Selective killing of tumors deficient in methylthioadenosine phosphorylase: a novel strategy.

  PloS one 20090101

• Primer fabrication using polymerase mediated oligonucleotide synthesis.

  BMC genomics 20090101

• An ab initio study of substituent effects on the excited states of purine derivatives.

  The journal of physical chemistry. A 20081204

• Structural effects of nucleobase variations at key active site residue Ade38 in the hairpin ribozyme.

  RNA (New York, N.Y.) 20080801

• Inhibition of the replication of hepatitis B virus in vitro by a novel 2,6-diaminopurine analog, beta-LPA.

  Biochemical and biophysical research communications 20080502

• Density functional and experimental studies on the FT-IR and FT-Raman spectra and structure of 2,6-diamino purine and 6-methoxy purine.

  Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20080101

• Mutational inhibition of ligation in the hairpin ribozyme: substitutions of conserved nucleobases A9 and A10 destabilize tertiary structure and selectively promote cleavage.

  RNA (New York, N.Y.) 20080101

• Solid-phase synthesis of pseudo-complementary peptide nucleic acids.

  Nature protocols 20080101

• Two specific drugs, BMS-345541 and purvalanol A induce apoptosis of HTLV-1 infected cells through inhibition of the NF-kappaB and cell cycle pathways.

  AIDS research and therapy 20080101

• Stability and mismatch discrimination of DNA duplexes containing 2,6-diaminopurine and 2-thiothymidine locked nucleic acid bases.

  Nucleic acids symposium series (2004) 20080101

• [(3)H]Adenine is a suitable radioligand for the labeling of G protein-coupled adenine receptors but shows high affinity to bacterial contaminations in buffer solutions.

  Purinergic signalling 20070901

• The screening and characterization of 6-aminopurine-based xanthine oxidase inhibitors.

  Bioorganic & medicinal chemistry 20070515

• Acyclic nucleoside phosphonate antivirals activate gene expression of monocyte chemotactic protein 1 and 3.

  Journal of biomedical science 20070101

• DNA polymerase mutations in drug-resistant herpes simplex virus mutants determine in vivo neurovirulence and drug-enzyme interactions.

  Antiviral therapy 20070101

• Characterization of copper(II) interactions with sinefungin, a nucleoside antibiotic: combined potentiometric, spectroscopic and DFT studies.

  Bioinorganic chemistry and applications 20070101

• Self-complementary purines by quadruple hydrogen bonding.

  Chemical communications (Cambridge, England) 20061113

• Structure-activity relationship studies on the immune stimulatory effects of base-modified CpG toll-like receptor 9 agonists.

  ChemMedChem 20060901

• Nucleotide analogues with immunobiological properties: 9-[2-Hydroxy-3-(phosphonomethoxy)propyl]-adenine (HPMPA), -2,6-diaminopurine (HPMPDAP), and their N6-substituted derivatives.

  European journal of pharmacology 20060701

• Calcium-stimulated guanosine--inosine nucleosidase from yellow lupin (Lupinus luteus).

  Phytochemistry 20060701

• Three conserved guanosines approach the reaction site in native and minimal hammerhead ribozymes.

  Biochemistry 20060613

• Thermodynamic and kinetic characterization of ligand binding to the purine riboswitch aptamer domain.

  Journal of molecular biology 20060609

• Exposure of mice to arsenic and/or benzo[a]pyrene does not increase the frequency of Aprt-deficient cells recovered from explanted skin of Aprt heterozygous mice.

  Environmental and molecular mutagenesis 20060601

• Purine P1 receptor-dependent immunostimulatory effects of antiviral acyclic analogues of adenine and 2,6-diaminopurine.

  European journal of pharmacology 20060113

• Highly efficient strand invasion by peptide nucleic acid bearing optically pure lysine residues in its backbone.

  Nucleic acids symposium series (2004) 20060101

• The kinetics of ligand binding by an adenine-sensing riboswitch.

  Biochemistry 20051011

• Unrestricted accessibility of short oligonucleotides to RNA.

  RNA (New York, N.Y.) 20050901

• Synthesis, characterisation and theoretical calculations of 2,6-diaminopurine etheno derivatives.

  Organic & biomolecular chemistry 20050821

• Model for general acid-base catalysis by the hammerhead ribozyme: pH-activity relationships of G8 and G12 variants at the putative active site.

  Biochemistry 20050531

• An investigation of prebiotic purine synthesis from the hydrolysis of HCN polymers.

  Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life 20050401

• Evidence for Watson-Crick and not Hoogsteen or wobble base pairing in the selection of nucleotides for insertion opposite pyrimidines and a thymine dimer by yeast DNA pol eta.

  Biochemistry 20050329

• Evidence for three thymine DNA glycosylases in human cell extracts: substrate specificities of thymine DNA glycosylase activities.

  Medical science monitor : international medical journal of experimental and clinical research 20050201

• Atomic force microscopy study of the structural effects induced by echinomycin binding to DNA.

  Journal of molecular biology 20050128

• Involvement of adenosine A1 receptors in upregulation of nitric oxide by acyclic nucleotide analogues.

  European journal of pharmacology 20041006

• Modified bases in RNA reduce secondary structure and enhance hybridization.

  Biochemistry 20040810

• Identification of the major tautomer for an etheno adduct of 2,6-diaminopurine by determination of the sign of (n)J(H,C).

  Organic letters 20040805

• Influence of minor groove substituents on the structure of DNA Holliday junctions.

  Biochemistry 20040803

• Syntheses and base-pairing properties of locked nucleic acid nucleotides containing hypoxanthine, 2,6-diaminopurine, and 2-aminopurine nucleobases.

  The Journal of organic chemistry 20040528

• LNA guanine and 2,6-diaminopurine. Synthesis, characterization and hybridization properties of LNA 2,6-diaminopurine containing oligonucleotides.

  Bioorganic & medicinal chemistry 20040501

• Attempt to reduce cytotoxicity by synthesizing the L-enantiomer of 4'-C-ethynyl-2'-deoxypurine nucleosides as antiviral agents against HIV and HBV.

  Antiviral chemistry & chemotherapy 20040501

• Functional group recognition at the aminoacylation and editing sites of E. coli valyl-tRNA synthetase.

  RNA (New York, N.Y.) 20040301

• In vitro selection of drug-resistant varicella-zoster virus (VZV) mutants (OKA strain): differences between acyclovir and penciclovir?

  Antiviral research 20040301

• Synthesis and antiviral activity of (Z)- and (E)-2,2-[bis(hydroxymethyl)cyclopropylidene]methylpurines and -pyrimidines: second-generation methylenecyclopropane analogues of nucleosides.

  Journal of medicinal chemistry 20040129

• Design, efficient synthesis, and anti-HIV activity of 4'-C-cyano- and 4'-C-ethynyl-2'-deoxy purine nucleosides.

  Nucleosides, nucleotides & nucleic acids 20040101

• Synthesis of base substituted 2-hydroxy-3-(purin-9-yl)-propanoic acids and 4-(purin-9-yl)-3-butenoic acids.

  Nucleosides, nucleotides & nucleic acids 20031201

• Cytostatic activity of antiviral acyclic nucleoside phosphonates in rodent lymphocytes.

  Toxicology and applied pharmacology 20031101

• Substrate analogues for an RNA-editing adenosine deaminase: mechanistic investigation and inhibitor design.

  Journal of the American Chemical Society 20030910

• Immunobiological activity of N-[2-(phosphonomethoxy)alkyl] derivatives of N6-substituted adenines, and 2,6-diaminopurines.

  European journal of pharmacology 20030815

• 3-Bromopyrazolo[3,4-d]pyrimidine 2'-deoxy-2'-fluoro-beta-D-arabinonucleosides: modified DNA constituents with an unusually rigid sugar N-conformation.

  The Journal of organic chemistry 20030711

• 2,6-Diamino-5,8-diaza-7,9-dicarba-purine.

  Organic letters 20030612

• C-Nucleosidations with 2,6-diamino-5,8-diaza-7,9-dicarba-purine.

  Organic letters 20030612

• Synthesis of (Z)-(2,3-bis-hydroxymethyl)methylenecyclopropane analogues of purine nucleosides.

  Nucleosides, nucleotides & nucleic acids 20030301

• Thermodynamic coupling of the loop and stem in unusually stable DNA hairpins closed by CG base pairs.

  Journal of the American Chemical Society 20030226

• The yeast ISN1 (YOR155c) gene encodes a new type of IMP-specific 5'-nucleotidase.

  BMC biochemistry 20030101

• Synthesis and antiviral activity of a series of new cyclohexenyl nucleosides.

  Antiviral chemistry & chemotherapy 20030101

• Chemo-enzymatic synthesis of 3-deoxy-beta-D-ribofuranosyl purines and study of their biological properties.

  Nucleosides, nucleotides & nucleic acids 20030101

• Crystal structure of calf spleen purine nucleoside phosphorylase in a complex with multisubstrate analogue inhibitor with 2,6-diaminopurine aglycone.

  Nucleosides, nucleotides & nucleic acids 20030101

• A ribozyme composed of only two different nucleotides.

  Nature 20021201

• 5-propynyluracil.diaminopurine: an efficient base-pair for non-enzymatic transcription of DNA.

  Chemical communications (Cambridge, England) 20020807

• DNA sequence recognition by the antitumor drug ditercalinium.

  Biochemistry 20020709

• 2,6-diaminopurine in TNA: effect on duplex stabilities and on the efficiency of template-controlled ligations.

  Organic letters 20020418

• Structure-activity relationships of 2'-fluoro-2',3'-unsaturated D-nucleosides as anti-HIV-1 agents.

  Journal of medicinal chemistry 20020314

• Novel antagonists acting at the P2Y(1) purinergic receptor: synthesis and conformational analysis using potentiometric and nuclear magnetic resonance titration techniques.

  Journal of medicinal chemistry 20020214

• Quantitative assessment of the use of modified nucleoside triphosphates in expression profiling: differential effects on signal intensities and impacts on expression ratios.

  BMC biotechnology 20020101

• Diaminopurine-acridine heterodimers for specific recognition of abasic site containing DNA. Influence on the biological activity of the position of the linker on the purine ring.

  Bioorganic & medicinal chemistry letters 20010723

• Hamster and rat fetal cells have low spontaneous mutation frequencies and rates.

  Mutation research 20010701

• Potentiation of BCNU cytotoxicity by molecules targeting abasic lesions in DNA.

  Bioorganic & medicinal chemistry 20010701

• Importance of specific nucleotides in the folding of the natural form of the hairpin ribozyme.

  Biochemistry 20010220

• Photolithographic synthesis of high-density oligonucleotide arrays.

  Methods in molecular biology (Clifton, N.J.) 20010101

• Antitumour activity of N6-substituted PMEDAP derivatives against T-cell lymphoma.

  Anticancer research 20010101

• Mechanism of action and in vitro activity of 1',3'-dioxolanylpurine nucleoside analogues against sensitive and drug-resistant human immunodeficiency virus type 1 variants.

  Antimicrobial agents and chemotherapy 19991001

• Structure-activity relationships for the binding of ligands to xanthine or guanine phosphoribosyl-transferase from Toxoplasma gondii.

  Biochemical pharmacology 19951109

• (+-)-carbocyclic 5'-nor-2'-deoxyguanosine and related purine derivatives: synthesis and antiviral properties.

  Journal of medicinal chemistry 19920612