2,6-DIAMINOPURINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H6N6
Molecular Weight	150.1413
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC(N)=C2N=CNC2=N1

InChI

InChIKey=MSSXOMSJDRHRMC-UHFFFAOYSA-N

InChI=1S/C5H6N6/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H5,6,7,8,9,10,11)

HIDE SMILES / InChI

Molecular Formula	C5H6N6
Molecular Weight	150.1413
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
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.	2010-11	21051822
Enzymatic synthesis of nucleosides by nucleoside phosphorylase co-expressed in Escherichia coli.	2010-11	21043057
Computational mutagenesis studies of hammerhead ribozyme catalysis.	2010-09-29	20812715
Comparisons between chemical mapping and binding to isoenergetic oligonucleotide microarrays reveal unexpected patterns of binding to the Bacillus subtilis RNase P RNA specificity domain.	2010-09-21	20557101
Antiviral treatment of chronic hepatitis B virus (HBV) infections.	2010-06	21994680
Inhibition of human immunodeficiency virus type-1 by cdk inhibitors.	2010-03-24	20334651
Role of the adenine ligand on the stabilization of the secondary and tertiary interactions in the adenine riboswitch.	2010-03-12	20026131
Preparation of the 2'-deoxynucleosides of 2,6-diaminopurine and isoguanine by direct glycosylation.	2010-03-05	20146451
Multivector fluorescence analysis of the xpt guanine riboswitch aptamer domain and the conformational role of guanine.	2010-03-02	20108980
Characterization of plant sulfiredoxin and role of sulphinic form of 2-Cys peroxiredoxin.	2010-03	20176891
Effect of substituents on the excited-state dynamics of the modified DNA bases 2,4-diaminopyrimidine and 2,6-diaminopurine.	2010	20379571
Reactions of Pd(II) with chelate-tethered 2,6-diaminopurine derivatives: N3-coordination and reaction of the purine system.	2009-12-07	19856895
Probing metal-ion purine interactions at DNA minor-groove sites.	2009-11-02	19799454
Two isomorphous crotonatolanthanide complexes: tetra-mu-but-2-enoato-bis[diaqua(but-2-enoato)Ln]-2,6-diaminopurine (1/2) (Ln = Dy and Ho).	2009-11	19893221
Co-expression of recombinant nucleoside phosphorylase from Escherichia coli and its application.	2009-10	19099210
Marine-derived metabolites of S-adenosylmethionine as templates for new anti-infectives.	2009-08-26	19841722
Primer fabrication using polymerase mediated oligonucleotide synthesis.	2009-07-31	19643029
Kinetic analysis of base-pairing preference for nucleotide incorporation opposite template pyrimidines by human DNA polymerase iota.	2009-06-05	19376129
Selective killing of tumors deficient in methylthioadenosine phosphorylase: a novel strategy.	2009-05-29	19478948
Monitoring RNA-ligand interactions using isothermal titration calorimetry.	2009	19381555
An ab initio study of substituent effects on the excited states of purine derivatives.	2008-12-04	18986130
Structural effects of nucleobase variations at key active site residue Ade38 in the hairpin ribozyme.	2008-08	18596253
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.	2008-06-10	18544167
Inhibition of the replication of hepatitis B virus in vitro by a novel 2,6-diaminopurine analog, beta-LPA.	2008-05-02	18284916
Mutational inhibition of ligation in the hairpin ribozyme: substitutions of conserved nucleobases A9 and A10 destabilize tertiary structure and selectively promote cleavage.	2008-01	17998292
Density functional and experimental studies on the FT-IR and FT-Raman spectra and structure of 2,6-diamino purine and 6-methoxy purine.	2008-01	17466577
Stability and mismatch discrimination of DNA duplexes containing 2,6-diaminopurine and 2-thiothymidine locked nucleic acid bases.	2008	18776345
Solid-phase synthesis of pseudo-complementary peptide nucleic acids.	2008	18388947
[(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.	2007-09	18404448
Acyclic nucleoside phosphonate antivirals activate gene expression of monocyte chemotactic protein 1 and 3.	2007-01	17033877
Characterization of copper(II) interactions with sinefungin, a nucleoside antibiotic: combined potentiometric, spectroscopic and DFT studies.	2007	18273386
DNA polymerase mutations in drug-resistant herpes simplex virus mutants determine in vivo neurovirulence and drug-enzyme interactions.	2007	17713155
Self-complementary purines by quadruple hydrogen bonding.	2006-11-13	17057861
Structure-activity relationship studies on the immune stimulatory effects of base-modified CpG toll-like receptor 9 agonists.	2006-09	16952134
Nucleotide analogues with immunobiological properties: 9-[2-Hydroxy-3-(phosphonomethoxy)propyl]-adenine (HPMPA), -2,6-diaminopurine (HPMPDAP), and their N6-substituted derivatives.	2006-07-01	16733050
Calcium-stimulated guanosine--inosine nucleosidase from yellow lupin (Lupinus luteus).	2006-07	16820181
Three conserved guanosines approach the reaction site in native and minimal hammerhead ribozymes.	2006-06-13	16752904
Thermodynamic and kinetic characterization of ligand binding to the purine riboswitch aptamer domain.	2006-06-09	16650860
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.	2006-06	16649189
Purine P1 receptor-dependent immunostimulatory effects of antiviral acyclic analogues of adenine and 2,6-diaminopurine.	2006-01-13	16371225
Highly efficient strand invasion by peptide nucleic acid bearing optically pure lysine residues in its backbone.	2006	17150841
The kinetics of ligand binding by an adenine-sensing riboswitch.	2005-10-11	16201765
Unrestricted accessibility of short oligonucleotides to RNA.	2005-09	16120834
Synthesis, characterisation and theoretical calculations of 2,6-diaminopurine etheno derivatives.	2005-08-21	16186923
Model for general acid-base catalysis by the hammerhead ribozyme: pH-activity relationships of G8 and G12 variants at the putative active site.	2005-05-31	15910000
An investigation of prebiotic purine synthesis from the hydrolysis of HCN polymers.	2005-04	16010991
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.	2005-03-29	15779911
Evidence for three thymine DNA glycosylases in human cell extracts: substrate specificities of thymine DNA glycosylase activities.	2005-02	15668625
Structure-activity relationships for the binding of ligands to xanthine or guanine phosphoribosyl-transferase from Toxoplasma gondii.	1995-11-09	7503772
Hydrogen exchange kinetics of nucleic acids. Double and triple helices with Hoogsteen-type basepairs.	1982-07-30	7115722

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:44:38 GMT 2025` Edited by `admin` on `Mon Mar 31 18:44:38 GMT 2025`
Record UNII	49P95BAU4Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-743

Preferred Name

English

2,6-DIAMINOPURINE

Systematic Name

English

DIAMINOPURINE, 2,6-

Systematic Name

English

9H-PURINE-2,6-DIAMINE

Systematic Name

English

2-AMINOADENINE

Systematic Name

English

2,6-DIAMINOPURINE [MI]

Common Name

English

2,6-DIAMINO-9H-PURINE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C786