Oxidation of sparteines by cytochrome P-450: evidence against the formation of N-oxides.
Oxidation of sparteines by cytochrome P-450: evidence against the formation of N-oxides.
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细胞色素 P-450 氧化金雀花碱：反对 N-氧化物形成的证据。
DOI：
10.1021/jm00375a002
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发表时间：
1984
影响因子：
7.3
通讯作者：
Guengerich,FP
中科院分区：
文献类型：
--
作者：
Guengerich,FP
(D20开头)。11、12、13由1在CH3OH中与H202反应生成；1313C核磁共振表明存在2和13的混合物；14结晶（乙醇）或氧化铝层析（乙酸乙酯/CHgOH）得到13为氢硫酸酯（mp 211-213℃），10为二氢硫酸酯（mp 244-245℃），10和游离碱的水合物（mp 108-110℃）；在78.66、73.81、65.55、61.27、58.34和56.29 ppm （D20）处有10个下场13C核磁共振峰；裂解游离碱13，真空蒸馏得到硫酸二氢酯9 （mp 240℃）；在190.57、68.93、59.18、56.80、56.49和56.32 ppm （D20）处有10个下场13C核磁共振峰。NaBH4在pH为8时还原9，用苯/醚在氧化铝上层析13得到7的二氢硫酸盐（mp为203-206℃，10 mp为癸二酸217-219℃），13得到简化的18C核磁共振谱，下峰为70.43、62.68和55.69 ppm
(D20). 11, 12 13 was formed from 1 by treatment with H202 in CH3OH; 1313C NMR indicated that a mixture of 2 and 13 was present; 14 crystallization (ethanol) or alumina chromatography (ethyl acetate/CHgOH) gave 13 as the hydrosulfate (mp 211-213 C), 10 the dihydrosulfate (mp 244-245 C), 10 and the hydrate of the free base (mp 108-110 C); 10 downfield 13C NMR peaks at 78.66, 73.81, 65.55, 61.27, 58.34, and 56.29 ppm (D20); IR 2806, 2765 cm" 1.16 Pyrrolysis15 of the free base of 13 and vacuum distillation yielded the dihydrosulfate of 9 (mp 240 C); 10 downfield 13C NMR peaks at 190.57, 68.93, 59.18, 56.80, 56.49, and 56.32 ppm (D20). NaBH4 reduction6 of 9 at pH 8 and chromatography on alumina with benzene/ether13 yielded the dihydrosulfate of 7 (mp 203-206 C; 10 mp of dipicrate 217-219 C), 13 which showed a simplified 18C NMR spectrum with downfield peaks at 70.43, 62.68, and 55.69 ppm