Bender Matthias, Mouritsen Henrik, Christoffers Jens
Institut für Chemie, Universität Oldenburg, Carl von Ossietzky-Str. 9-11, D-26129 Oldenburg, Germany.
Institut für Biologie und Umweltwissenschaften, Universität Oldenburg, D-26111 Oldenburg, Germany; Centre for Neurosensory Sciences, University of Oldenburg, D-26111 Oldenburg, Germany.
Beilstein J Org Chem. 2016 May 6;12:912-7. doi: 10.3762/bjoc.12.89. eCollection 2016.
The biosynthetic precursor of redox cofactor F420, 7,8-didemethyl-8-hydroxy-5-deazariboflavin, was prepared in four steps from 6-chlorouracil, 2-chloro-4-hydroxybenzaldehyde and bis-isopropylidene protected D-ribose. The latter aldehyde was transformed to the corresponding protected ribitylamine via the oxime, which was submitted to reduction with LiAlH4. Key advantage compared to previous syntheses is the utilization of a polyol-protective group which allowed the chromatographic purification of a key-intermediate product providing the target compound with high purity.
氧化还原辅因子F420的生物合成前体，即7,8-二去甲基-8-羟基-5-去氮杂黄素，由6-氯尿嘧啶、2-氯-4-羟基苯甲醛和双异丙叉基保护的D-核糖分四步制备而成。后一种醛通过肟转化为相应的保护核糖胺，再用氢化铝锂进行还原。与之前的合成方法相比，关键优势在于使用了一种多元醇保护基团，这使得关键中间体产物能够通过色谱法纯化，从而得到高纯度的目标化合物。
