Recent developments in genetic analysis techniques have facilitated search and discovery of biosynthetic enzymes in natural product chemistry. However, structural analysis of biosynthetic enzyme products still relies on NMR, which requires large amounts of samples and mass spectrometry, which gives only limited structural information, often hampering structural analysis of enzymatic products obtained in biosynthetic studies.
In this study, we applied the crystalline sponge (CS) method, which is capable of elucidating absolute stereochemistry of analytes from trace amounts of samples, to biosynthetic studies, and rapidly revealed the absolute structures of enzymatic products. A putative terpene cyclase LphTPS-C, obtained from the mRNA sequence of the red alga Laurencia pacifica, produced a small amount of sesquiterpenol 1 (total yield: 0.1 mg) with a yeast heterologous expression system. Purification of 1 followed by structural analysis by the CS method revealed its novel structure, that is named haraldol in our work. In this presentation, we report the preparation method of 1, the detailed structural analysis by the CS method, and the unique radical-mediated transannular rearrangement from 1 to 2.

Complete Structural Determination of Novel Sesquiterpenoids in Microgram Scales by the Crystalline Sponge Method

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