喹啉
吲哚试验
色氨酸
部分
戒指(化学)
立体化学
化学
生物合成
氨基酸
生物化学
酶
有机化学
作者
Athula B. Attygalle,Kithsiri B. Hearth,Vikram K. Iyengar,Randy C. Morgan
标识
DOI:10.1021/acs.jnatprod.0c00945
摘要
The Peruvian stick insect Oreophoetes peruana is the only known animal source for unsubstituted quinoline in nature. When disturbed, these insects discharge a defensive secretion containing quinoline. Analysis of samples obtained from l-[2′,4′,5′,6,′7′-2H5]tryptophan-fed stick insects demonstrated that the insects convert it to [5,6,7,8-2H4]quinoline by removing the 2′-CH moiety in the indole ring of tryptophan. Analogous experiments using l-[1′-15N]tryptophan and l-[1′-15N,15NH2]tryptophan showed that the indole-N atom is retained while the α-amino group is eliminated during the biosynthesis. Mass spectra recorded from quinoline derived from [2-13C1]tryptophan-fed insects indicated that the α-carbon atom of tryptophan is incorporated as the C-2 atom of the quinoline ring.
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