Oxidative Dimerization

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Satoshi Minakata - One of the best experts on this subject based on the ideXlab platform.

Youhei Takeda - One of the best experts on this subject based on the ideXlab platform.

Sota Okumura - One of the best experts on this subject based on the ideXlab platform.

Tsutomu Nakayama - One of the best experts on this subject based on the ideXlab platform.

  • efficient synthesis of theaflavin 3 gallate by a tyrosinase catalyzed reaction with epicatechin and epigallocatechin gallate in a 1 octanol buffer biphasic system
    Journal of Agricultural and Food Chemistry, 2018
    Co-Authors: Asako Naraikanayama, Yoshinori Uekusa, Fumiyuki Kiuchi, Tsutomu Nakayama
    Abstract:

    Theaflavins, the orange-red pigments contained in black tea, have attracted attention as a result of their health-promoting effects. However, their synthetic preparation, in which the enzymatic oxidation of catechol-type catechin is followed by the quinone-induced Oxidative Dimerization of selectively combined catechol- and pyrogallol-type catechins, provides only a low yield. In the present study, we found that a 1-octanol/buffer biphasic system improved the yield of theaflavin 3-gallate in a tyrosinase-catalyzed synthetic reaction with (-)-epicatechin and (-)-epigallocatechin gallate. When the enzymatic reaction proceeded in a buffer solution, oxidized (-)-epigallocatechin gallate was preferentially used for self-Dimerization. However, self-Dimerization was suppressed in the octanol phase, allowing oxidized (-)-epigallocatechin gallate to participate in coupling with (-)-epicatechin quinone, leading to effective production of theaflavin 3-gallate. Furthermore, the preferential localization of theaflavin 3-gallate in the octanol phase prevented (-)-epicatechin-quinone-induced degradation.

  • Efficient Synthesis of Theaflavin 3‑Gallate by a Tyrosinase-Catalyzed Reaction with (−)-Epicatechin and (−)-Epigallocatechin Gallate in a 1‑Octanol/Buffer Biphasic System
    2018
    Co-Authors: Asako Narai-kanayama, Yoshinori Uekusa, Fumiyuki Kiuchi, Tsutomu Nakayama
    Abstract:

    Theaflavins, the orange–red pigments contained in black tea, have attracted attention as a result of their health-promoting effects. However, their synthetic preparation, in which the enzymatic oxidation of catechol-type catechin is followed by the quinone-induced Oxidative Dimerization of selectively combined catechol- and pyrogallol-type catechins, provides only a low yield. In the present study, we found that a 1-octanol/buffer biphasic system improved the yield of theaflavin 3-gallate in a tyrosinase-catalyzed synthetic reaction with (−)-epicatechin and (−)-epigallocatechin gallate. When the enzymatic reaction proceeded in a buffer solution, oxidized (−)-epigallocatechin gallate was preferentially used for self-Dimerization. However, self-Dimerization was suppressed in the octanol phase, allowing oxidized (−)-epigallocatechin gallate to participate in coupling with (−)-epicatechin quinone, leading to effective production of theaflavin 3-gallate. Furthermore, the preferential localization of theaflavin 3-gallate in the octanol phase prevented (−)-epicatechin-quinone-induced degradation

Yuming Zhao - One of the best experts on this subject based on the ideXlab platform.