Laboratoire de Biogéochimie Moléculaire, Université de Strasbourg, Institut de Chimie de Strasbourg, Strasbourg.
Chem Biodivers. 2012 Apr;9(4):714-26. doi: 10.1002/cbdv.201100124.
We report here a novel reductive coupling reaction of conjugated, non- or poorly enolizable aldehydes induced by H(2) S and operative in aqueous solutions under prebiotically relevant conditions. This reaction leads from retinal to β-carotene, and from benzylic aldehydes to the corresponding diarylethylenes. This novel reaction also opens a new potentially prebiotic pathway leading from glyoxylic acid to various compounds that are involved in the reductive tricarboxylic acid cycle. This C--C bond forming reaction of prebiotic interest might have been operative, notably, in the sulfide-rich environments of hydrothermal vents, which have been postulated as possible sites for the first steps of organic chemical evolution.
我们在此报告了一种新型的还原偶联反应，该反应由 H(2)S 诱导，在类似原始生命条件的水溶液中对共轭的、非烯醇化或烯醇化能力差的醛类起作用。该反应可将视黄醛转化为β-胡萝卜素，将苄基醛转化为相应的二芳基乙烯。该新型反应还开辟了一条新的、潜在的前生物途径，可使糖醛酸转化为参与还原三羧酸循环的各种化合物。这种具有前生物意义的 C--C 键形成反应可能在热液喷口富硫环境中起作用，热液喷口被认为是有机化学进化的第一步的可能发生地点。
