Enzymatic Synthesis of β-Glucosylglycerol and Its Unnatural Glycosides Via β-Glycosidase and Amylosucrase |
Jung, Dong-Hyun
(Graduate School of Biotechnology and Institute of Life Science and Resources, Kyung Hee University)
Seo, Dong-Ho (Research Group of Healthcare, Korea Food Research Institute) Park, Ji-Hae (Graduate School of Biotechnology and Department of Oriental Medicinal Biotechnology, Kyung Hee University) Kim, Myo-Jung (Department of Food and Life Science, Inje University) Baek, Nam-In (Graduate School of Biotechnology and Department of Oriental Medicinal Biotechnology, Kyung Hee University) Park, Cheon-Seok (Graduate School of Biotechnology and Institute of Life Science and Resources, Kyung Hee University) |
1 | Bianchi G, Gamba A, Limiroli R, Pozzi N, Elster R, Salamini F, et al. 1993. The unusual sugar composition in leaves of the resurrection plant Myrothamnus flabellifolia. Physiol. Plant. 87: 223-226. DOI |
2 | Kaneda M, Mizutani K, Takahashi Y, Kurono G, Nishikawa Y. 1974. Lilioside A and B, two new glycerol glucosides isolated from Lilium longiflorum T hunb. Tetrahedron Lett. 15: 3937-3940. DOI |
3 | Seo S, Tomita Y, Tori K, Yoshimura Y. 1978. Determination of the absolute configuration of a secondary hydroxy group in a chiral secondary alcohol using glycosidation shifts in carbon-13 nuclear magnetic resonance spectroscopy. J. Am. Chem. Soc. 100: 3331-3339. DOI |
4 | Suhr R, Scheel O, Thiem J. 1998. Synthesis of glycosyl glycerols and related glycolipids. J. Carbohydr. Chem. 17: 937-968. DOI |
5 |
Colombo D, Scala A, Taino IM, Toma L, Ronchetti F, Tokuda H, et al. 1998. Inhibitory effects of fatty acid monoesters of 2-O- |
6 | Kaneda M, Mizutani K, Tanaka K. 1982. Lilioside C, a glycerol glucoside from Lilium lancifolium. Phytochemistry 21: 891-893. DOI |
7 | Curatolo W. 1987. The physical properties of glycolipids. Biochim. Biophys. Acta-Rev. 906: 111-136. DOI |
8 |
Colombo D, Scala A, Taino IM, Toma L, Ronchetti F, Tokuda H, et al. 1996. 1-O-, 2-O-and 3-O- |
9 |
Colombo D, Compostella F, Ronchetti F, Scala A, Toma L, Tokuda H, et al. 1999. Chemoenzymatic synthesis and antitumor promoting activity of 6'-and 3-esters of 2-O- |
10 | Murakami N, Imamura H, Sakakibara J, Yamada N. 1990. Seven new monogalactosyl diacylglycerols isolated from the axenic cyanobacterium Phormidium tenue. Chem. Pharm. Bull. 38: 3497-3499. DOI |
11 | Shirahashi H, Murakami N, Watanabe M, Nagatsu A, Sakakibara J, Tokuda H, et al. 1993. Isolation and identification of anti-tumor-promoting principles from the fresh-water cyanobacterium Phormidium tenue. Chem. Pharm. Bull. 41: 1664-1666. DOI |
12 | Murakami A, Nakamura Y, Koshimizu K, Ohigashi H. 1995. Glyceroglycolipids from Citrus hystrix, a traditional herb in Thailand, potently inhibit the tumor-promoting activity of 12-O-tetradecanoylphorbol 13-acetate in mouse skin. J. Agric. Food Chem. 43: 2779-2783. DOI |
13 | Morimoto T, Nagatsu A, Murakami N, Sakakibara J, Tokuda H, Nishino H, et al. 1995. Anti-tumour-promoting glyceroglycolipids from the green alga, Chlorella vulgaris. Phytochemistry 40: 1433-1437. DOI |
14 | Barstrom M, Bengtsson M, Blixt O, Norberg T. 2000. New derivatives of reducing oligosaccharides and their use in enzymatic reactions: efficient synthesis of sialyl Lewis a and sialyl dimeric Lewis x glycoconjugates. Carbohydr. Res. 328: 525-531. DOI |
15 | Boltje TJ, Buskas T, Boons G-J. 2009. Opportunities and challenges in synthetic oligosaccharide and glycoconjugate research. Nat. Chem. 1: 611-622. DOI |
16 | Marinone Albini F, Murelli C, Patritti G, Rovati M. 1994. A simple synthesis of glucosyl glycerols. Synth. Commun. 24: 1651-1661. DOI |
17 | Wickberg B. 1958. Synthesis of 1-glyceritol D-galactopyranosides. Acta Chem. Scand. 12: 1187-1201. DOI |
18 |
Zeng X, Uzawa H. 2005. Convenient enzymatic synthesis of a p-nitrophenyl oligosaccharide series of sialyl N-acetyllactosamine, sialyl |
19 |
Bruins M, Strubel M, Van Lieshout J, Janssen A, Boom R. 2003. Oligosaccharide synthesis by the hyperthermostable |
20 | Henrissat B, Davies G. 1997. Structural and sequence-based classification of glycoside hydrolases. Curr. Opin. Struct. Biol. 7: 637-644. DOI |
21 |
Park N-Y, Baek N-I, Cha J, Lee S-B, Auh J-H, Park C-S. 2005. Production of a new sucrose derivative by transglycosylation of recombinant Sulfolobus shibatae |
22 | Tian Y, Xu W, Zhang W, Zhang T, Guang C, Mu W. 2018. Amylosucrase as a transglucosylation tool: from molecular features to bioengineering applications. Biotechnol. Adv. 36: 1540-1552. DOI |
23 | Jung D-H, Jung J-H, Seo D-H, Ha S-J, Kweon D-K, Park C-S. 2013. One-pot bioconversion of sucrose to trehalose using enzymatic sequential reactions in combined cross-linked enzyme aggregates. Bioresour. Technol. 130: 801-804. DOI |
24 |
Hinz SW, Verhoef R, Schols HA, Vincken J-P, Voragen AG. 2005. Type I arabinogalactan contains |
25 | Cho H-K, Kim H-H, Seo D-H, Jung J-H, Park J-H, Baek N-I, et al. 2011. Biosynthesis of (+)-catechin glycosides using recombinant amylosucrase from Deinococcus geothermalis DSM 11300. Enzyme Microb. Technol. 49: 246-253. DOI |
26 | Jung J-H, Seo D-H, Ha S-J, Song M-C, Cha J, Yoo S-H, et al. 2009. Enzymatic synthesis of salicin glycosides through transglycosylation catalyzed by amylosucrases from Deinococcus geothermalis and Neisseria polysaccharea. Carbohydr. Res. 344: 1612-1619. DOI |
27 |
Mikami B, Adachi M, Kage T, Sarikaya E, Nanmori T, Shinke R, et al. 1999. Structure of raw starch-digesting Bacillus cereus |
28 |
Seo D-H, Jung J-H, Ha S-J, Cho H-K, Jung D-H, Kim T-J, et al. 2012. High-yield enzymatic bioconversion of hydroquinone to |
29 |
De Roode M, Peters SW, Franssen MC, Van Padt AD, De Groot A, Boom RM. 2001. Optimization of production and downstream processing of the almond |
30 | Jeong J-W, Seo D-H, Jung J-H, Park J-H, Baek N-I, Kim M-J, et al. 2014. Biosynthesis of glucosyl glycerol, a compatible solute, using intermolecular transglycosylation activity of amylosucrase from Methylobacillus flagellatus KT. Appl. Biochem. Biotechnol. 173: 904-917. DOI |
31 | Cassel S, Debaig C, Benvegnu T, Chaimbault P, Lafosse M, Plusquellec D, et al. 2001. Original synthesis of linear, branched and cyclic oligoglycerol standards. Eur. J. Org. Chem. 2001: 875-896. DOI |
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