Natural Pericosines B and C as Enantiomeric Mixtures: Direct Evidence by Chiral HPLC Analysis

作者：Usami Yoshihide^*; Okada Yusuke; Yamada Takeshi

来源：Chirality, 2011, 23(1E): E7-E11.

DOI：10.1002/chir.20937

• pericosine B, C
• natural product
• fungal metabolite
• carbasugar
• enantiomeric mixture
• chiral HPLC analysis

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 enantio-separation of these racemic carbasugars was conducted with CHIRALPAK1 IA and CHIRALPAK1 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. Chirality 23: E7-E11, 2011.

• 出版日期2011