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Ashibe S, Ikeuchi K, Kume Y, et al. Non-Enzymatic Oxidation of a Pentagalloylglucose Analogue into Members of the Ellagitannin Family. Angew Chem Int Ed Engl. 2017;56(48):15402-15406doi: 10.1002/anie.201708703.
Ashibe, S., Ikeuchi, K., Kume, Y., Wakamori, S., Ueno, Y., Iwashita, T., & Yamada, H. (2017). Non-Enzymatic Oxidation of a Pentagalloylglucose Analogue into Members of the Ellagitannin Family. Angewandte Chemie (International ed. in English), 56(48), 15402-15406. https://doi.org/10.1002/anie.201708703
Ashibe, Seiya, et al. "Non-Enzymatic Oxidation of a Pentagalloylglucose Analogue into Members of the Ellagitannin Family." Angewandte Chemie (International ed. in English) vol. 56,48 (2017): 15402-15406. doi: https://doi.org/10.1002/anie.201708703
Ashibe S, Ikeuchi K, Kume Y, Wakamori S, Ueno Y, Iwashita T, Yamada H. Non-Enzymatic Oxidation of a Pentagalloylglucose Analogue into Members of the Ellagitannin Family. Angew Chem Int Ed Engl. 2017 Nov 27;56(48):15402-15406. doi: 10.1002/anie.201708703. Epub 2017 Nov 02. PMID: 29024258.
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Angew Chem Int Ed Engl. 2017 Nov 27;56(48):15402-15406. doi: 10.1002/anie.201708703. Epub 2017 Nov 02.

Non-Enzymatic Oxidation of a Pentagalloylglucose Analogue into Members of the Ellagitannin Family.

Angewandte Chemie (International ed. in English)

Seiya Ashibe, Kazutada Ikeuchi, Yuji Kume, Shinnosuke Wakamori, Yuri Ueno, Takashi Iwashita, Hidetoshi Yamada

Affiliations

  1. School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, 669-1337, Japan.
  2. Bioorganic Research Institute, Suntory Foundation for Life Sciences, 8-1-1 Seikadai, Seika-cho, Soraku-gun, Kyoto 619-0284, Japan.

PMID: 29024258 DOI: 10.1002/anie.201708703

Abstract

The occurrence of more than 1000 structurally diverse ellagitannins has been hypothesized to begin with the oxidation of penta-O-galloyl-β-d-glucose (β-PGG) for the coupling of the galloyl groups. However, the non-enzymatic behavior of β-PGG in the oxidation is unknown. Disclosed herein is which galloyl groups tended to couple and which axial chirality was predominant in the derived hexahydroxydiphenoyl groups when an analogue of β-PGG was subjected to oxidation. The galloyl groups coupled in the following order: at the 4,6-, 1,6-, 1,2-, 2,3-, and 3,6-positions with respective S-, S-, R-, S-, and R-axial chirality. Among them, the most preferred 4,6-coupling reflected the what was observed for natural ellagitannins. A new finding was that the second best coupling occured at the 1,6-positions. With the detection of a 3,6-coupled product, this work demonstrated that even ellagitannin skeletons with an axial-rich glucose core may be generated non-enzymatically.

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: C−C coupling; ellagitannins; natural products; oxidation; polyphenols

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