Itano H A, Hirota T
Biochem J. 1985 Mar 15;226(3):767-71. doi: 10.1042/bj2260767.
Coupled oxidation of octaethylhaemin and phenylhydrazine hydrochloride with 16,16O2 and 18,18O2 produced octaethyl[16O]verdohaemochrome and octaethyl[18O]-verdohaemochrome respectively. Reactions of these products with 16,16O2 in the presence of phenylhydrazine hydrochloride yielded octaethyl[16O, 16O]biliverdin and octaethyl[18O, 16O]biliverdin. The same reactions with 18,18O2 yielded octaethyl[16O, 18O]biliverdin and octaethyl[18O, 18O]biliverdin. Accordingly, the two oxygen atoms of biliverdin are incorporated from different O2 molecules in separate reactions, namely the formation of verdohaemochrome and the conversion of verdohaemochrome into biliverdin. These reactions account for a "two-molecule mechanism' of biliverdin formation from haem with verdohaemochrome participating as an intermediate product.
八乙基血红素与盐酸苯肼分别与(^{16,16}O_2)和(^{18,18}O_2)的偶联氧化反应分别生成了八乙基([^{16}O])胆绿素和八乙基([^{18}O])胆绿素。在盐酸苯肼存在下,这些产物与(^{16,16}O_2)反应生成了八乙基([^{16}O,^{16}O])胆红素和八乙基([^{18}O,^{16}O])胆红素。与(^{18,18}O_2)进行的相同反应生成了八乙基([^{16}O,^{18}O])胆红素和八乙基([^{18}O,^{18}O])胆红素。因此,胆红素的两个氧原子是在不同的反应中从不同的(O_2)分子中掺入的,即胆绿素的形成以及胆绿素向胆红素的转化。这些反应说明了血红素形成胆红素的“双分子机制”,其中胆绿素作为中间产物参与反应。