Gutnick D L, Dunphy P J, Sakamoto H, Phillips P G, Brodie A F
Science. 1967 Dec 15;158(3807):1469-71. doi: 10.1126/science.158.3807.1469.
Synthetic phylloquinone was resolved into cis and trans isomers by thin-layer chromatography. The two isomers had identical ultraviolet spectra characteristic of vitamin K(1) and were differentiated by nuclear-magnetic-resonance spectroscopy on the basis of the displacement of the peak corresponding to the olefinic methyl group in the naphthoquinone side chain. Studies on the restoration of electron transport coupled to phosphorylation in irradiated preparations of Mycobacterium phlei showed that only the trans isomer was active with substrates linked to nicotinamide-adenine dinucleotide. The purified trans phylloquinone was enzymatically converted to the cis isomer. Under similar conditions, cis vitamin K(1) gave rise to the trans-naphthoquinone. The natural naphthoquinone of M. phlei vitamin MK(9)(II-H) was similarly resolved into cis and trans isomers.
合成叶绿醌通过薄层色谱法被分离为顺式和反式异构体。这两种异构体具有相同的维生素K(1)特征紫外光谱，并通过核磁共振光谱法根据萘醌侧链中烯丙基甲基对应峰的位移进行区分。对辐照的草分枝杆菌制剂中与磷酸化偶联的电子传递恢复的研究表明，只有反式异构体对与烟酰胺腺嘌呤二核苷酸相连的底物具有活性。纯化的反式叶绿醌被酶促转化为顺式异构体。在类似条件下，顺式维生素K(1)产生反式萘醌。草分枝杆菌维生素MK(9)(II-H)的天然萘醌同样被分离为顺式和反式异构体。
