Studies on the Azidoazomethine— Tetrazole Equilibrium. V. 2- and 6-Azidopurines<sup>1</sup>

Temple, Carroll; Kussner, Conrad L.

doi:10.1021/jo01345a031

Cited by 75 publications

(33 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A minor disadvantage of 2-azido nucleotides is their spontaneous isomerization to form a tetrazole ring [4]. 2-Azido-p-32P]ADP has been applied to chloroplast F1 and found to bind to a tight site on the fl subunit [ 11.…”

Section: Introductionmentioning

confidence: 99%

Exploration of nucleotide binding sites in the mitochondrial membrane by 2‐azido‐[α‐³²P]ADP

Boulay

Vignais

1985

FEBS Letters

View full text Add to dashboard Cite

The ADP/ATP carrier of beef heart mitochondria is able to bind 2-azido-[G2P]ADP in the dark with a Kd value of 'c 8 ,uM. 2-Azido ADP is not transported and it inhibits ADP transport and ADP binding. Photoirradiation of beef heart mitochondria with 2-azido-[a-32P]ADP results mainly in photolabeling of the ADP/ATP carrier protein; photolabeling is prevented by carboxyatractyloside, a specific inhibitor of ADP/ ATP transport. Upon photoirradiation of inside-out submitochondrial particles with 2-azido-[c+P]ADP, both the ADP/ATP carrier and the p subunit of the membrane-bound F,-ATPase are covalently labeled. The binding specificity of 2-azido-[cc-32P]ADP for the B subunit of F,-ATPase is ascertained by prevention of photolabeling of isolated F, by preincubation with an excess of ADP. Nucleotide binding Mitochondrial membrane 2-Azido-[a-32P]ATP

show abstract

Section: Introductionmentioning

confidence: 99%

Exploration of nucleotide binding sites in the mitochondrial membrane by 2‐azido‐[α‐³²P]ADP

Boulay

Vignais

1985

FEBS Letters

View full text Add to dashboard Cite

show abstract

“…Moreover, from a structure-activity consideration, it is of interest that a co-planar, electron-withdrawing group which protrudes from the ring with geometry corresponding approximately to 6 (22) causes no diminution in cytokinin activity. Because the existence of an azidoazomethine-tetrazole equilibrium for lb and 2b (60,61) in effect lowers the concentration of the azide, the intrinsic activities of the azides may differ from the reported values.…”

Section: Cytokinin Activitymentioning

confidence: 76%

“…Excess acetal was evaporated in vacuo to give a viscous yellow oil, 8-chloro-9-( 1- 2-Azido-trans-zeatin or 2-Azido-6(4-hydroxy-3-methyl-(E)-2-butenylamino)purine (3b). A mixture of 2,6-diazidopurine (from 2 mmol of 2,6-dichloropurine) (53,60), 600 mg (4 mmol) of 4-hydroxy-3-methyl-(E)-2-butenylamine sulfate, 15 ml of water, and 1.5 ml of triethylamine was heated at reflux for 5 h. After cooling to room temperature and neutralization with dilute H2SO4, the solvent was evaporated in vacuo, 20 ml of water was added, and the mixture was cooled overnight. The …”

Section: Methodsmentioning

confidence: 99%

“…We have reported the synthesis and cytokinin activity in the tobacco bioassay of two new azidopurines, 2-azido-6-(3-methyl-2-butenylamino)purine (2-azido-N6-(A2-isopentenyl)adenine) (2b) and 2-azido-6-benzylaminopurine (2-azido-N6-benzyladenine) (lb) (62). Although these compounds are quite active, especially 2b, and thus satisfy the requirement of photoaffmity-labeling reagents by behaving as natural substrates, the system is complicated by the presence of both azido and tetrazolo forms of the purines whose equilibrium is solvent-dependent (60,61). This candidates for such comparison are the o-and p-azido-substituted N6-benzyladenines (4c, f), since Okumura and his co-workers (41), using the radish leaf growth bioassay, showed that in several series of substituted N6-benzyladenines, the o-isomer was generally more active than the m-and p-isomers.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Active Cytokinins

et al. 1979

View full text Add to dashboard Cite

Four series of azidopurines have been synthesized and tested for cytokinin activity in the tobacco callus bioassay: 2-and 8-azido-N6-benzyladenines, -N -(A2-isopentenyl)adenines, and -zeatins, and N -(2-and 4-azidobenzyl)adenines. The compounds having 2-azido substitution on the adenine ring are as active as the corresponding parent compounds, while those with 8-azido substitution are about 10 or more times as active. The 8-azidozeatin, which is the most active cytokinin observed, exhibited higher than minimal detectable activity at 1.2 x 10-5 micromolar, the lowest concentration tested. The shape of the growth curve indicates that even a concentration as low as 5 x 10-6 micromolar would probably be effective. By comparison, the lowest active concentration ever reported for zeatin has been 5 x 10-5 micromolar, representing a sensitivity rarely attained.All of the azido compbunds have been submitted to photolysis in aqueous ethanol, and the photoproducts have been detected and identified by low and high resolution mass spectrometry. They are rationalized as products of abstraction and insertion reactions of the intermediate nitrenes. The potential of the major released products as cytokinins was also assessed by bioassay. 2-Azido-N6-(A2-isopentenyl)adenine competed with 114CIki-netin for the cytokinin-binding protein isolated from wheat germ. When the azido compound was photolysed in the presence of this protein, its attachment effectively blocked the binding of 114Clkinetin.Extensive studies of structure-activity relationships for cytokinins have led to a well-defined concept of the chemical nature of '

show abstract

“…Silica gel column chromatography (Toluene/EtOAc = 2 : 1) provided product 7 (10.6 g, 51%) as yellow foam. 2,6-Diazidopurine (8) [15] A solution of sodium azide (8.25 g, 126.9 mmol) in water (30 mL) was added to a stirred suspension of 2,6-dichloropurine (6.00 g, 31.7 mmol) in ethanol (60 mL). The resulting mixture was stirred and refluxed for 5 min and after that cooled to ambient temperature.…”

Section: -(2'3'4'-tri-o-acetyl-α-d-arabinopyranosyl)-26-dichloropmentioning

confidence: 99%

The Synthesis and X-ray Studies of 6-pyrrolidinyl-2-triazolyl Purine Arabinonucleoside

Novosjolova

Bizdēna

Belyakov

et al. 2013

Material Science and Applied Chemistry

View full text Add to dashboard Cite

Abstract. C(6)-Pyrrolidinyl derivative with triazolyl moiety at C(2)-position was obtained from 2,6-bis-triazolylpurine arabinonucleoside via C(6)-regioselective nucleophilic substituon of 1,2,3-triazolyl moiety with pyrrolidine. The obtained compound was studied by NMR, X-ray, UV/VIS and emission spectra. Pyranose form of arabinose residue and α-configuration of the obtained compound were unambiguously proven by NMR and X-ray studies.

show abstract

Studies on the Azidoazomethine— Tetrazole Equilibrium. V. 2- and 6-Azidopurines¹

Cited by 75 publications

References 0 publications

Exploration of nucleotide binding sites in the mitochondrial membrane by 2‐azido‐[α‐³²P]ADP

Exploration of nucleotide binding sites in the mitochondrial membrane by 2‐azido‐[α‐³²P]ADP

Active Cytokinins

The Synthesis and X-ray Studies of 6-pyrrolidinyl-2-triazolyl Purine Arabinonucleoside

Contact Info

Product

Resources

About

Studies on the Azidoazomethine— Tetrazole Equilibrium. V. 2- and 6-Azidopurines1

Cited by 75 publications

References 0 publications

Exploration of nucleotide binding sites in the mitochondrial membrane by 2‐azido‐[α‐32P]ADP

Exploration of nucleotide binding sites in the mitochondrial membrane by 2‐azido‐[α‐32P]ADP

Active Cytokinins

The Synthesis and X-ray Studies of 6-pyrrolidinyl-2-triazolyl Purine Arabinonucleoside

Contact Info

Product

Resources

About

Studies on the Azidoazomethine— Tetrazole Equilibrium. V. 2- and 6-Azidopurines¹

Exploration of nucleotide binding sites in the mitochondrial membrane by 2‐azido‐[α‐³²P]ADP

Exploration of nucleotide binding sites in the mitochondrial membrane by 2‐azido‐[α‐³²P]ADP