The Biosynthesis of Nicotine from Isotopically Labeled Nicotinic Acids1
The Biosynthesis of Nicotine from Isotopically Labeled Nicotinic Acids1
复制标题
从同位素标记的烟酸生物合成尼古丁1
DOI：
10.1021/ja01495a059
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发表时间：
1960
影响因子：
15
通讯作者：
A. Wolf
中科院分区：
文献类型：
--
作者：
R. F. Dawson;D. Christman;A. D'adamo;M. Solt;A. Wolf
制备了四种特异性环氢标记烟酸，并将其在无菌培养基中培养于烟草根培养物中。然后对根产生的烟碱进行分离和分析。类似地使用反冲氚和碳-14标记的烟曲霉酸。除烟酸-6-t外，所有这些化合物的尼古丁均表现出类似的和实质性的掺入尼古丁中。烟酸的氧化。从nlcotlne获得。与相应的2-和6-吡啶酮的反应表明氢标记的位置在转化为尼古丁的过程中是保守的。6-标记酸的掺入量不到其它酸的10%。表明烟酸在被烟草根转化为烟碱的过程中，可能受到酶的攻击。转化可能不会通过6位的氧化进行，因为6-羟基烟酸-N/sup 15/和1甲基-6-氧烟酰胺-2-t都未能被掺入。正在研究酸通过1，6-二氢中间体掺入尼古丁的可能性。烟酸酯的掺入程度至少与相应的标记酸一样大。（auth）
The four specific ring hydrogen-labeled nicotinic acids were prepared and fed to tobacco root cultures In sterile media. then the nicotine produced by the roots was Isolated and analyzed. Recoil tritium and carbon-14 labeled nlcotinic acid were similarly employed. The nicotine from all of these except nicotinic acid-6-t show similar and substantial incorroration into the nicotine. Oxidation of nicotinic acid. obtained from the nlcotlne. to the corresponding 2- and 6-pyridones indicate that the position of hydrogen label is conserved during the conversion to nicotine. The 6-labeled acid gave less than 10% of the amount of incorporation shown by the other acids Indicatlng the probablllty of enzymatic attack on the 6-position of nicotinic acid dur ing Its conversion to nicotine by the tobacco roots. The conversion probably does not proceed via oxidation at the 6-position, since both 6-hydroxynicotinic acid-N/sup 15/ and 1methyl-6- oxynicotinamide-2-t failed to be Incorporated. The possibility that the acid is incorporated into nicotine via a 1,6-dinydro intermediate is being investigated. Nicotinartide is incorporated to at least as great an extent as is the corresponding labeled acid. (auth)