Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H13N5O2 |
| Molecular Weight | 235.2425 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H]1O[C@H](C[C@@H]1O)N2C=NC3=C2N=CN=C3N
InChI
InChIKey=FFHPXOJTVQDVMO-DSYKOEDSSA-N
InChI=1S/C10H13N5O2/c1-5-6(16)2-7(17-5)15-4-14-8-9(11)12-3-13-10(8)15/h3-7,16H,2H2,1H3,(H2,11,12,13)/t5-,6+,7-/m1/s1
2',5'-dideoxyadenosine (DDA), a P-site specific adenylate cyclase inhibitor, inhibited the growth of K562 cells and caused them to become benzidine positive. Adenine, a possible metabolite of DDA digestion by purine nucleoside phosphorylase (PNP), also induced erythroid differentiation in K562 cells.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Further investigation on the turnover of Escherichia coli biotin synthase with dethiobiotin and 9-mercaptodethiobiotin as substrates. | 2004 Dec 28 |
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| Structure and function of radical SAM enzymes. | 2004 Oct |
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| S-adenosylmethionine radical enzymes. | 2004 Oct |
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| Insight into the polar reactivity of the onium chalcogen analogues of S-adenosyl-L-methionine. | 2004 Oct 26 |
|
| Suicide inactivation of dioldehydratase by glycolaldehyde and chloroacetaldehyde: an examination of the reaction mechanism. | 2004 Oct 6 |
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| Escherichia coli lipoyl synthase binds two distinct [4Fe-4S] clusters per polypeptide. | 2004 Sep 21 |
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| Spectroscopic approaches to elucidating novel iron-sulfur chemistry in the "radical-Sam" protein superfamily. | 2005 Feb 21 |
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| Isotope effects for deuterium transfer between substrate and coenzyme in adenosylcobalamin-dependent glutamate mutase. | 2005 Feb 22 |
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| Nitric oxide inhibits mammalian methylmalonyl-CoA mutase. | 2005 Mar 18 |
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| Preliminary mechanistic studies on the smooth muscle relaxant effect of hydroalcoholic extract of Curcuma caesia. | 2006 |
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| Quantum catalysis in B12-dependent methylmalonyl-CoA mutase: experimental and computational insights. | 2006 Aug 29 |
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| Computational insights into the mechanism of radical generation in B12-dependent methylmalonyl-CoA mutase. | 2006 Feb 1 |
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| Signaling pathways for modulation of mouse sperm motility by adenosine and catecholamine agonists. | 2006 Mar |
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| Role of the [2Fe-2S]2+ cluster in biotin synthase: mutagenesis of the atypical metal ligand arginine 260. | 2006 Nov 28 |
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| Biotin synthase mechanism: mutagenesis of the YNHNLD conserved motif. | 2006 Oct 10 |
|
| Enantiomeric free radicals and enzymatic control of stereochemistry in a radical mechanism: the case of lysine 2,3-aminomutases. | 2006 Oct 24 |
|
| Structural and signaling requirements of the human melanocortin 4 receptor for MAP kinase activation. | 2007 Aug 16 |
|
| Phylogeny of the nematode genus Pristionchus and implications for biodiversity, biogeography and the evolution of hermaphroditism. | 2007 Jul 2 |
|
| Probing interactions from solvent-exchangeable protons and monovalent cations with the 1,2-propanediol-1-yl radical intermediate in the reaction of dioldehydrase. | 2007 Jun |
|
| Thiazole synthase from Escherichia coli: an investigation of the substrates and purified proteins required for activity in vitro. | 2007 Jun 15 |
|
| Dioldehydrase: an essential role for potassium ion in the homolytic cleavage of the cobalt-carbon bond in adenosylcobalamin. | 2007 Jun 19 |
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| 5'-Peroxyadenosine and 5'-peroxyadenosylcobalamin as intermediates in the aerobic photolysis of adenosylcobalamin. | 2007 Jun 19 |
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| S-adenosylmethionine as an oxidant: the radical SAM superfamily. | 2007 Mar |
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| S-Adenosylmethionine in protozoan parasites: functions, synthesis and regulation. | 2007 Mar |
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| Binding energy in the one-electron reductive cleavage of S-adenosylmethionine in lysine 2,3-aminomutase, a radical SAM enzyme. | 2007 Nov 13 |
|
| Self-sacrifice in radical S-adenosylmethionine proteins. | 2007 Oct |
|
| Iron-sulfur proteins as initiators of radical chemistry. | 2007 Oct |
|
| Mechanistic study on the reaction of a radical SAM dehydrogenase BtrN by electron paramagnetic resonance spectroscopy. | 2008 Aug 26 |
|
| Relaxant action mechanism of berberine identified as the active principle of Argemone ochroleuca Sweet in guinea-pig tracheal smooth muscle. | 2008 Feb |
|
| Lipolysis is stimulated by PEGylated conjugated linoleic acid through the cyclic adenosine monophosphate-independent signaling pathway in 3T3-L1 cells: activation of MEK/ERK MAPK signaling pathway and hyper-secretion of adipo-cytokines. | 2008 Feb |
|
| The Radical SAM Superfamily. | 2008 Jan-Feb |
|
| Crystallization and preliminary X-ray crystallographic studies of a PduO-type ATP:cob(I)alamin adenosyltransferase from Bacillus cereus. | 2008 Jul 1 |
|
| In vitro characterization of AtsB, a radical SAM formylglycine-generating enzyme that contains three [4Fe-4S] clusters. | 2008 Jul 15 |
|
| The pyrroloquinoline quinone biosynthesis pathway revisited: a structural approach. | 2008 Mar 27 |
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| Structural characterization of a human-type corrinoid adenosyltransferase confirms that coenzyme B12 is synthesized through a four-coordinate intermediate. | 2008 May 27 |
|
| 9-Mercaptodethiobiotin is formed as a competent catalytic intermediate by Escherichia coli biotin synthase. | 2008 Sep 2 |
|
| DFT and ONIOM(DFT:MM) studies on Co-C bond cleavage and hydrogen transfer in B12-dependent methylmalonyl-CoA mutase. Stepwise or concerted mechanism? | 2009 Apr 15 |
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| Product inhibition in the radical S-adenosylmethionine family. | 2009 Apr 17 |
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| Processing of alkylcobalamins in mammalian cells: A role for the MMACHC (cblC) gene product. | 2009 Aug |
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| Anaerobic functionalization of unactivated C-H bonds. | 2009 Feb |
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| Comparative genomic analyses of nickel, cobalt and vitamin B12 utilization. | 2009 Feb 10 |
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| A comparative genomics study of genetic products potentially encoding ladderane lipid biosynthesis. | 2009 Feb 16 |
|
| Delineation of the chemomechanosensory regulation of gastrin secretion using pure rodent G cells. | 2009 Jul |
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| Gastric relaxation induced by apigenin and quercetin: analysis of the mechanism of action. | 2009 Jul 3 |
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| Mechanistic investigations of anaerobic sulfatase-maturating enzyme: direct Cbeta H-atom abstraction catalyzed by a radical AdoMet enzyme. | 2009 Jun 24 |
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| Biochemical characterization of the GTP:adenosylcobinamide-phosphate guanylyltransferase (CobY) enzyme of the hyperthermophilic archaeon Methanocaldococcus jannaschii. | 2009 Jun 30 |
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| Protein residues that control the reaction trajectory in S-adenosylmethionine radical enzymes: mutagenesis of asparagine 153 and aspartate 155 in Escherichia coli biotin synthase. | 2009 Mar 24 |
|
| Stabilization of the base-off forms of vitamin B(12) and coenzyme B(12) by encapsulation of the alpha-axial 5,6-dimethylbenzimidazole ligand with cucurbit[7]uril. | 2009 May 14 |
|
| Ligand-binding by catalytically inactive mutants of the cblB complementation group defective in human ATP:cob(I)alamin adenosyltransferase. | 2009 Nov |
|
| Characterization and mechanistic studies of DesII: a radical S-adenosyl-L-methionine enzyme involved in the biosynthesis of TDP-D-desosamine. | 2009 Oct 7 |
Sample Use Guides
In Vitro Use Guide
Curator's Comment: Membranes from rat cerebral cortex and striatum contain a relatively large number of high-affinity binding sites for [3H]2',5'-dideoxyadenosine, [3H]adenine arabinoside, and [3H]adenosine. The binding of [3H]2',5'-dideoxyadenosine and [3H]adenine arabinoside was virtually unaffected by relatively specific agonists and antagonists for adenosine receptors, such as 2-chloroadenosine. 5'-Methylthioadenosine had high potency and efficacy versus binding of [3H]2',5'-dideoxyadenosine but had virtually no effect on activity of adenylate cyclase. 2-Fluoroadenosine was less potent than adenosine as an antagonist of specific binding of [3H]2',5'-dideoxyadenosine.
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6698-26-6
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988H339Z1L
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95943
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65166
Created by
admin on Fri Dec 15 18:12:03 GMT 2023 , Edited by admin on Fri Dec 15 18:12:03 GMT 2023
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SUBSTANCE RECORD
