Purine N-oxides. 54. Chemical adduct of tryptophan and the oncogen 3-acetoxyxanthine

Stöhrer, Gerhard; Salemnick, Gad; Gb, Brown

doi:10.1021/bi00749a009

Cited by 10 publications

(4 citation statements)

References 11 publications

(12 reference statements)

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“…13 This reactivity was subsequently shown to be a general property of all IV-(acyloxy)purines that could undergo nucleophilic substitution. 21,23,25 In each instance iodide ion could completely eliminate 8-substitution in favor of a redox reaction, affording iodine and the parent purine.…”

Section: Discussionmentioning

confidence: 99%

“…16,19 Only C-substitution products have been isolated from reactions of jV-(acyloxy)purines with nucleophiles in vitro11"13,15 or in vivo. 6,8,21,22 This alkylating reactivity may account for the oncogenic properties of some purine JV-oxides.…”

mentioning

confidence: 99%

“…In particular, the use of substituent chemical shifts (SCS) to monitor the transmission of electronic effects in rigid molecular frameworks has been a fruitful area of research for many years.1-10 Studies have been made of the transmission of substituent effects both within aromatic rings1'3,5,9•11-14 and in (often unsaturated) side chains attached to those substituted aromatic systems. [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29] The most successful analyses of substituent effects on chemical shifts have used Hammett-type30 treatments. The dual substituent parameter (DSP)31 extension of the * To whom correspondence should be addressed.…”

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confidence: 99%

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Competitive reactivity of nitrenium and carbenium ion contributors of purinium cations with "soft" bases

Parham¹,

Templeton²

1982

J. Org. Chem.

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CaHaOll, mol wt 632.76). The intensity data were collected on a Picker FACS-1 diffractometer equipped with a graphite monochromator (Mo K a radiation, h = 0.71069) and with modified Nonius low-temperature device.'* A crystal measuring approximately 0.15 X 0.35 X 0.5 mm was used for data collection at 96 K. Cooling was used in order to increase the number of observed reflections, which was very limited at room temperature.A total of 5827 independent reflections were measured (0 < 30') of which 3889 were considered to be observed [I > 2.Oo(I)]. The data were not corrected for absorption (p = 1.01 cm-l).The structure was solved by direct methods, using the program m T A N 1 3 and refied by full-matrix leaat-squarea methods, using the X-RAY system.14 The 48 H atoms were located in difference maps. In the final refinement anisotropic thermal parameters were used for C and 0 atoms, and isotropic temperature factors (B = 2.0 &?) were used for H atoms, but only positional parameters

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Section: Discussionmentioning

confidence: 99%

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confidence: 99%

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Competitive reactivity of nitrenium and carbenium ion contributors of purinium cations with "soft" bases

Parham¹,

Templeton²

1982

J. Org. Chem.

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“…The two isomers are isolated in a combined yield of 25%. Simultaneously, a portion of tryptophan is oxidized to unidentified colored products and a portion (30%) is recovered (388). This reaction with tryptophan could have specific effects on mechanism of cellular control, since aromatic amino acids play a role in the specific binding of proteins to DNA.…”

Section: Reaction With Diazonium Saltsmentioning

confidence: 99%