Verification of Biaryl-Structure Axial Chirality Produced in Ellagitannins by Chemical Oxidation

The axial chirality of hexahydroxydiphenoyl (HHDP) groups contained in ellagitannins depends on the bridging position of d-glucose. The 4,6-O-HHDP group predominantly exhibits S-type chirality. This study elucidated the formation of the 4,6-O-(R)-HHDP group and subsequent axial isomerization by mean...

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Published inOrganic letters Vol. 24; no. 44; pp. 8130 - 8135
Main Authors Wakamori, Shinnosuke, Osada, Rumi, Matsumoto, Shintaro, Kusuki, Reina, Murakami, Kei
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 11.11.2022
Subjects
Glucose
Hydrolyzable Tannins
Molecular Structure
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Summary:The axial chirality of hexahydroxydiphenoyl (HHDP) groups contained in ellagitannins depends on the bridging position of d-glucose. The 4,6-O-HHDP group predominantly exhibits S-type chirality. This study elucidated the formation of the 4,6-O-(R)-HHDP group and subsequent axial isomerization by means of oxidative coupling of galloyl groups, which resulted in S chirality.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03173