Department of Pharmaceutical Sciences Laboratory of Pharmaceutical Organic Chemistry, Osaka University of Pharmaceutical Sciences, Takatsuki, Osaka, Japan.
Chirality. 2011;23 Suppl 1:E7-11. doi: 10.1002/chir.20937. Epub 2011 Mar 23.
Pericosines are carbasugar-type metabolites of Periconia byssoides OUPS-N133, a fungus that was originally separated from the sea hare Aplysia kurodai. It has been reported that pericosines C and E are enantiomeric mixtures. The difference in specific rotation between natural pericosine C and the synthetic one led to the conclusion that natural pericosine C is an enantiomeric mixture. Meanwhile, the small specific rotation of natural pericosine B compared to that of the synthetic one led to the deduction that natural pericosine B might also be an enantiomeric mixture. Then, racemic pericosines B and C were synthesized, and the direct enantioseparation of these racemic carbasugars was conducted with CHIRALPAK® IA and CHIRALPAK® AY-H, which are suitable columns for racemic pericosines B and C, respectively. Using chiral HPLC, we conclude that natural pericosines B and C exist as enantiomeric mixtures. A rare example of the application of direct chiral HPLC analysis to intact sugars or carbasugars was provided.
佩里科辛是一种真菌，最初是从海兔 Aplysia kurodai 中分离出来的，其代谢产物是佩里科尼亚毕索迪斯 OUPS-N133 的碳环糖型代谢产物。有报道称，佩里科辛 C 和 E 是对映体混合物。天然佩里科辛 C 的比旋光度与合成品的比旋光度的差异导致了天然佩里科辛 C 是对映体混合物的结论。同时，天然佩里科辛 B 的比旋光度与合成品的比旋光度相比，推断出天然佩里科辛 B 也可能是对映体混合物。然后，合成了外消旋的佩里科辛 B 和 C，并使用 CHIRALPAK® IA 和 CHIRALPAK® AY-H 对这些外消旋的碳环糖进行直接对映体分离，这两种柱适合于外消旋的佩里科辛 B 和 C。通过手性 HPLC，我们得出结论，天然佩里科辛 B 和 C 是对映体混合物。提供了一个直接手性 HPLC 分析应用于完整糖或碳环糖的罕见实例。
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