cas 5142-23-4, 3-METHYLADENINE | Articles data

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A versatile methodology for the regioselective C8-metalation of purine bases
Purine nucleobases are excellent ligands for metal ions, forming normally coordinative Werner-type bonds by utilizing the N donor atoms of the nucleobase skeleton. Here we show that purines such as 8-chlorocaffeine and 8-bromo-9-methyladenine react with [Pt(PPh3)4] under oxidative addition of the C8-halogen bond to the metal center. The resulting PtII complexes feature a C8-bound ylidene ligand. Protonation of the ylidene at the N7/9-atom yields complexes bearing a protic N-heterocyclic carbene ligand derived from the purine base with an NMe,NH-substitution pattern.
Brackemeyer, Dirk,Hervé, Alexandre,Schulte To Brinke, Christian,Jahnke, Mareike C.,Hahn, F. Ekkehardt
p. 7841 - 7844
(2014)
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Characterization of substrate binding and enzymatic removal of a 3-methyladenine lesion from genomic DNA with TAG of MDR A. baumannii
The rise of multiple-drug resistance in bacterial pathogens imposes a serious public health concern and has led to increased interest in studying various pathways as well as enzymes. Different DNA glycosylases collaborate during bacterial infection and disease by overcoming the effects of ROS- and RNS-mediated host innate immunity response. 3-Methyladenine DNA glycosylase I, an essential DNA repair enzyme, was chosen for the present study from the MDR species of A. baumannii. The enzyme was especially chosen because of its functional significance in A. baumannii and due to its structural variation from its human homologue. MDR strains such as A. baumannii are interesting targets owing to their evolved mechanisms of evading a host defence. In the absence of any structural information, the enzyme was characterized biophysically and biochemically. Binding studies with 3mA and Zn2+ indicated that the activity of TAG-Ab is an enthalpy-driven process. Fluorescence thermal denaturation studies described that the denaturation of TAG-Ab is a two-step process. Modified RP-HPLC-based glycosylase assay attested that the heterologously expressed and purified TAG-Ab enzyme is active and catalyses the removal of 3mA. Other binding parameters and the effect of adenine on substrate binding are also discussed in detail.
Tomar, Jyoti Singh,Narwal, Manju,Kumar, Pravindra,Peddinti, Rama Krishna
p. 3259 - 3265
(2016)
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Saito,Fujii
p. 135
(1979)
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Purines. LXVI. Adenine 7-oxide: Its synthesis, chemical properties, and X-ray molecular structure
A detailed account is given of the first unequivocal synthesis of adenine 7-oxide (8). The synthesis started with peroxycarboxylic acid oxidation of 3-benzyladenine (6), readily obtainable from adenine (1) by benzylation, and proceeded through nonreductive debenzylation of the resulting 3-benzyladenine 7-oxide (7). The location of the oxygen function in 7 and 8 was confirmed by their chemical reactions including deamination and methylation and by X-ray crystallographic analysis. A UV spectroscopic approach suggested that the neutral species of 8 exists in H2O as an equilibrated mixture of the NO-oxide (8) and N(7)-OH (21) tautomers. Treatment of 6 with 30% aqueous H2O2 in MeOH in the presence of MeCN and KHCO3 at 30°C produced the N(7)-oxide 7 and 7-acetamido-3-benzyladenine (15) in 12% and 1% yields, respectively.
Fujii,Ogawa,Saito,Kobayashi,Itaya,Date,Okamura
p. 53 - 62
(2007/10/02)

SYNTHESIS OF ADENINE 7-OXIDE FROM ADENINE: UTILIZATION OF A BENZYL GROUP AS A CONTROL SYNTHON AT THE 3-POSITION
The first unequivocal synthetic route to adenine 7-oxide (7) has been established.The route started with peroxycarboxylic acid oxidation of 3-benzyladenine (5), readily obtainable from adenine (2) by benzylation, 8nd proceeded through nonreductive debenzylation of the resulting 3-benzyladenine 7-oxide (6).
Fujii, Tozo,Ogawa, Kazuo,Saito, Tohru,Kobayashi, Keiko,Itaya, Taisuke
p. 477 - 480
(2007/10/02)

Purines. XXXII. Synthesis and ring fission of 3,9-dialkyladenines
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Fujii,Itaya,Saito,Mohri,Kawanishi,Nakasaka
p. 1504 - 1513
(2007/10/02)

Purines. XXXIV. 3-Methyladenosine and 3-methyl-2'-deoxyadenosine: their synthesis, glycosidic hydrolysis, and ring fission
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Fujii,Saito,Nakasaka
p. 2601 - 2609
(2007/10/02)

Heterocyclic Ambident Nucleophiles. III* The Alkylation of Sodium Adenide
The alkylation of sodium adenide in HCONMe2 (30 deg) with various alkylating agents was analysed by 1H n.m.r. spectroscopy.Widely varying N3:N7:N9 alkylation patterns were observed, depending on the alkylating agent.These patterns are interpreted in terms of the electrostatic, thermodynamic and steric factors involved in the different SN2 transition states appropriate to each alkylating agent.Hydrogen bonding association between the 6-amino group and certain carbonyl containing alkylating agents is proposed to explain the enhancedN7-alkylation in some cases.Support for this latter proposal was obtain from a comparison of the adenine alkylation results with the corresponding alkylation patterns of 6-pivaloylamino- and 6-chloro-purine.
Rasmussen, Malcolm,Hope, Janet M.
p. 525 - 534
(2007/10/02)

Synthesis, Ring Opening, and Glycosidic Bond Cleavage of 3-Methyl-2'-deoxyadenosine
Methylation of N'-benzyloxy-1-(2-deoxy-β-D-ribofuranosyl)-5-formamidoimidazole-4-carboxamidine (2a) followed by hydrogenolysis of the N'-benzyloxy-group and cyclization produced the hitherto unknown 3-methyl-2'-deoxyadenosine (5a), which was readily hydrolysed to 3-methyladenine (6) in H2O at pH /=7.0 and to (6) and the imidazole-(2-deoxy)riboside (4a) at pH 8.98.
Fujii, Tozo,Saito, Tohru,Nakasaka, Tsuyoshi
p. 758 - 759
(2007/10/02)