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氘代腺苷藿烷的半合成以及通过嗜有机甲基杆菌的无细胞系统转化为细菌藿四醇。

Hemisynthesis of deuteriated adenosylhopane and conversion into bacteriohopanetetrol by a cell-free system from Methylobacterium organophilum.

作者信息

Liu Wenjun, Bodlenner Anne, Rohmer Michel

机构信息

Université de Strasbourg/CNRS, Institut Le Bel, 4 rue Blaise Pascal, F 67070 Strasbourg, Cedex, France.

出版信息

Org Biomol Chem. 2015 Mar 21;13(11):3393-405. doi: 10.1039/c4ob02560a.

Abstract

Adenosylhopane is a putative precursor of the widespread bacterial C35 biohopanoids. A concise and flexible hemisynthesis of adenosylhopane has been developed including as key steps a cross metathesis between two olefins containing either the hopane moiety or a protected adenosine derivative and a subsequent diimide reduction of the resulting olefin. Reduction by deuteriated diimide allowed deuterium labelling. This synthetic protocol represents a versatile tool to access to deuteriated composite bacterial hopanoids required for biosynthetic studies. Deuteriated adenosylhopane was thus converted into bacteriohopanetetrol by a crude cell-free system from Methylobacterium organophilum in the presence of NADPH, showing for the first time the precursor to product relationship between these two bacterial metabolites.

摘要

腺苷藿烷是广泛存在的细菌C35生物藿烷类化合物的一种假定前体。已开发出一种简洁且灵活的腺苷藿烷半合成方法,其关键步骤包括含藿烷部分的烯烃与受保护的腺苷衍生物之间的交叉复分解反应,以及随后对所得烯烃进行二亚胺还原。用氘代二亚胺还原可实现氘标记。该合成方案是获取生物合成研究所需的氘代复合细菌藿烷类化合物的通用工具。因此,在NADPH存在的情况下,通过嗜有机甲基杆菌的粗无细胞体系将氘代腺苷藿烷转化为细菌藿四醇,首次展示了这两种细菌代谢物之间从前体到产物的关系。

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