Abstract
α-Arbutin, a useful cosmetic ingredient, was selectively synthesized by α-anomer-selective glucosylation of hydroquinone with maltose as a glucosyl donor using lyophilized cells of Xanthomonas campestris WU-9701 as a biocatalyst. When 45 mM hydroquinone and 120 mg of lyophilized cells showing 11 nkat of α-glucosyl transfer activity were shaken in 2 ml of 10 mM H3BO3-NaOH-KCl buffer (pH 7.5) containing 1.2 M maltose at 40°C, only one form of hydroquinone glucoside was selectively obtained as a product and identified as hydroquinone 1-O-α-D-glucopyranoside (α-arbutin) by 13C-NMR, 1H-NMR and two-dimensional HMBC analysis. Although hydroquinone has two phenolic -OH groups at the para position in its structure, only one -OH group, but not both -OHs, was glucosylated and no other glucosylated products such as maltotriose were detected in the reaction mixture. The reaction at 40°C for 36 h under optimum conditions yielded 42 mM α-arbutin, and the maximum molar conversion yield based on the amount of hydroquinone supplied reached 93%.
| Original language | English |
|---|---|
| Pages (from-to) | 328-330 |
| Number of pages | 3 |
| Journal | Journal of Bioscience and Bioengineering |
| Volume | 93 |
| Issue number | 3 |
| DOIs | |
| Publication status | Published - 2002 |
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Keywords
- α-anomer-selective glucosylation
- α-arbutin
- Hydroquinone
- Transglucosylation
- Xanthomonas campestris
ASJC Scopus subject areas
- Biotechnology
- Bioengineering
Cite this
Enzymatic synthesis of α-arbutin by α-anomer-selective glucosylation of hydroquinone using lyophilized cells of Xanthomonas campestris WU-9701. / Kurosu, Jun; Sato, Toshiyuki; Yoshida, Keishiro; Tsugane, Takanori; Shimura, Susumu; Kirimura, Kotaro; Kino, Kuniki; Usami, Shoji.
In: Journal of Bioscience and Bioengineering, Vol. 93, No. 3, 2002, p. 328-330.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Enzymatic synthesis of α-arbutin by α-anomer-selective glucosylation of hydroquinone using lyophilized cells of Xanthomonas campestris WU-9701
AU - Kurosu, Jun
AU - Sato, Toshiyuki
AU - Yoshida, Keishiro
AU - Tsugane, Takanori
AU - Shimura, Susumu
AU - Kirimura, Kotaro
AU - Kino, Kuniki
AU - Usami, Shoji
PY - 2002
Y1 - 2002
N2 - α-Arbutin, a useful cosmetic ingredient, was selectively synthesized by α-anomer-selective glucosylation of hydroquinone with maltose as a glucosyl donor using lyophilized cells of Xanthomonas campestris WU-9701 as a biocatalyst. When 45 mM hydroquinone and 120 mg of lyophilized cells showing 11 nkat of α-glucosyl transfer activity were shaken in 2 ml of 10 mM H3BO3-NaOH-KCl buffer (pH 7.5) containing 1.2 M maltose at 40°C, only one form of hydroquinone glucoside was selectively obtained as a product and identified as hydroquinone 1-O-α-D-glucopyranoside (α-arbutin) by 13C-NMR, 1H-NMR and two-dimensional HMBC analysis. Although hydroquinone has two phenolic -OH groups at the para position in its structure, only one -OH group, but not both -OHs, was glucosylated and no other glucosylated products such as maltotriose were detected in the reaction mixture. The reaction at 40°C for 36 h under optimum conditions yielded 42 mM α-arbutin, and the maximum molar conversion yield based on the amount of hydroquinone supplied reached 93%.
AB - α-Arbutin, a useful cosmetic ingredient, was selectively synthesized by α-anomer-selective glucosylation of hydroquinone with maltose as a glucosyl donor using lyophilized cells of Xanthomonas campestris WU-9701 as a biocatalyst. When 45 mM hydroquinone and 120 mg of lyophilized cells showing 11 nkat of α-glucosyl transfer activity were shaken in 2 ml of 10 mM H3BO3-NaOH-KCl buffer (pH 7.5) containing 1.2 M maltose at 40°C, only one form of hydroquinone glucoside was selectively obtained as a product and identified as hydroquinone 1-O-α-D-glucopyranoside (α-arbutin) by 13C-NMR, 1H-NMR and two-dimensional HMBC analysis. Although hydroquinone has two phenolic -OH groups at the para position in its structure, only one -OH group, but not both -OHs, was glucosylated and no other glucosylated products such as maltotriose were detected in the reaction mixture. The reaction at 40°C for 36 h under optimum conditions yielded 42 mM α-arbutin, and the maximum molar conversion yield based on the amount of hydroquinone supplied reached 93%.
KW - α-anomer-selective glucosylation
KW - α-arbutin
KW - Hydroquinone
KW - Transglucosylation
KW - Xanthomonas campestris
UR - http://www.scopus.com/inward/record.url?scp=0036098664&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0036098664&partnerID=8YFLogxK
U2 - 10.1016/S1389-1723(02)80037-8
DO - 10.1016/S1389-1723(02)80037-8
M3 - Article
C2 - 16233209
AN - SCOPUS:0036098664
VL - 93
SP - 328
EP - 330
JO - Journal of Bioscience and Bioengineering
JF - Journal of Bioscience and Bioengineering
SN - 1389-1723
IS - 3
ER -