Abstract
A novel transglycosylation reaction from sucrose to l-ascorbic acid by a recombinant sucrose phosphorylase from Bifidobacterium longum was used to produce a stable l-ascorbic acid derivative. The major product was detected by HPLC, and confirmed to be 2-O-α-d-glucopyranosyl-l-ascorbic acid by LC-MS/MS analysis.
Similar content being viewed by others
References
Aga H, Yoneyama M, Sakai S, Yamamoto I (1991) Synthesis of 2-O-α-d-glucopyranosyl l-ascorbic acid by cyclomaltodextrin glucanotransferase from Bacillus stearothermophilus. Agric Biol Chem 55:1751–1756
Bae H-K, Lee S-B, Park C-S, Shim J-H, Lee H-Y, Kim M-J, Baek J-S, Roh H-J, Choi J-H, Choe E-O, Ahn D-U, Park K-H (2002) Modification of ascorbic acid using transglycosylation activity of Bacillus stearothermophilus maltogenic amylase to enhance its oxidative stability. J Agri Food Chem 50:3309–3316
Elliott JG (1999) Application of antioxidant vitamins in foods and beverages. Food Technol 53:46–48
Kim M, Kwon T, Lee HJ, Kim KH, Chung DK, Ji GE, Byeon E-S, Lee J-H (2003) Cloning and expression of sucrose phosphorylase gene from Bifidobacterium longum in E. coli and characterization of the recombinant enzyme. Biotechnol Lett 25:1211–1217
Kitao S, Ariga T, Matsudo T, Sekine H (1993) The synthesis of catechin-glucosides by transglycosylation with Leuconostoc mesenteroides sucrose phosphorylase. Biosci Biotechnol Biochem 57:2010–2015
Kitao S, Matsudo T, Saitoh M, Horiuchi T, Sekine H (1995) Enzymatic synthesis of two stable (−)-epigallocatechin gallate-glucosides by sucrose phosphorylase. Biosci Biotechnol Biochem 59:2167–2169
Kitao S, Matsudo T, Sasaki T, Koga T, Kawamura M (2000) Enzymatic synthesis of stable, odorless, and powdered furanone glucosides by sucrose phosphorylase. Biosci Biotechnol Biochem 64:134–141
Kitao S, Sekine H (1992) Transglucosylation catalyzed by sucrose phosphorylase from Leuconostoc mesenteroides and production of glucosyl-xylitol. Biosci Biotechnol Biochem 56:2011–2014
Kitao S, Sekine H (1994) α-d-Glucosyl transfer to phenolic compounds by sucrose phosphorylase from Leuconostoc mesenteroides and production of α-arbutin. Biosci Biotechnol Biochem 58:38–42
Murad S, Grove D, Lindberg KA, Reynolds G, Sivarajah A, Pinnell SR (1981) Regulation of collagen synthesis by ascorbic acid. Proc Natl Acad Sci USA 78:2879–2882
Muto N, Nakamura T, Yamamoto I (1990a) Enzymatic formation of a nonreducing l-ascorbic acid α-glucoside: purification and properties of α-glucosidases catalyzing site-specific transglucosylation from rat small intestine. J Biochem 107:222–227
Muto N, Suga S, Fujii K, Goto K, Yamamoto I (1990b) Formation of a stable ascorbic acid 2-glucoside by specific transglucosylation with rice seed α-glucosidase. Agric Biol Chem 54:1697–1703
Vandamme EJ, van Loo J, Machtelinckx L, de Laporte A (1987) Microbial sucrose phosphorylase: fermentation process, properties, and biotechnical applications. Adv Appl Microbiol 32:163–201
Wakamiya H, Suzuki E, Yamamoto I, Akiba M, Otsuka M, Arakawa N (1992) Vitamin C activity of 2-O-α-d-glucopyranosyl-l-ascorbic acid in guinea pigs. J Nutr Sci Vitaminol 38:235–245
Wakamiya H, Suzuki E, Yamamoto I, Akiba M, Arakawa N (1995) In situ intestinal absorption of 2-O-α-d-glucopyranosyl-l-ascorbic acid in guinea pigs. J Nutr Sci Vitaminol 41:265–272
Yamamoto I, Muto N, Nagata E, Nakamura T, Suzuki Y (1990) Formation of a stable l-ascobic acid α-glucoside by mammalian α-glucosidase catalyzed transglucosylation. Biochim Biophys Acta 1035:44–50
Acknowledgement
This research was supported by Kyonggi University Overseas Research Grant 2004.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kwon, T., Kim, C. & Lee, JH. Transglucosylation of ascorbic acid to ascorbic acid 2-glucoside by a recombinant sucrose phosphorylase from Bifidobacterium longum . Biotechnol Lett 29, 611–615 (2007). https://doi.org/10.1007/s10529-006-9285-2
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10529-006-9285-2