Relative Stereochemistry Determination and Synthesis of the Major Chlorosulfolipid from Ochromonas danica

Relative Stereochemistry Determination and Synthesis of the Major Chlorosulfolipid from Ochromonas danica
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DOI:
10.1021/ja902138w
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发表时间:
2009-06-10
影响因子:
15
通讯作者:
Vanderwal, Christopher D.
Vanderwal, Christopher D.
中科院分区:
化学1区
文献类型:
--
作者:
Bedke, D. Karl;Shibuya, Grant M.;Vanderwal, Christopher D.

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本文报道了绿藻(Ochromonas danica)中主要氯磺酸脂的相对立体化学性质,我们将其命名为“danicalipin A”。这种脂质的第一次合成,通过几个立体定向的亲电添加到烯烃上,用于证实核磁共振波谱所作的立体化学分配。所描述的合成策略应适用于其他氯亚脂,并应提供充分的材料,以研究脂质的性质和功能的膜。
The relative stereochemistry of the major chlorosulfolipid of the chrysophyte alga Ochromonas danica, to which we have given the name "danicalipin A", is reported. The first synthesis of this lipid, via several stereospecific electrophilic additions to alkenes, serves to corroborate the stereochemical assignment made by NMR spectroscopy. The synthesis strategy described should be applicable to other chlorosulfolipids and should provide access to sufficient material for studies of the lipid's properties and function in membranes.