• Journal of Microbiology and Biotechnology
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• 제31권12호
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• pp.1692-1700
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• 2021

Glycosylation of resveratrol was carried out by using the amylosucrase of Deinococcus geothermalis, and the glycosylated products were tested for their solubility, chemical stability, and biological activities. We synthesized and identified these two major glycosylated products as resveratrol-4'-O-α-glucoside and resveratrol-3-O-α-glucoside by nuclear magnetic resonance analysis with a ratio of 5:1. The water solubilities of the two resveratrol-α-glucoside isomers (α-piceid isomers) were approximately 3.6 and 13.5 times higher than that of β-piceid and resveratrol, respectively, and they were also highly stable in buffered solutions. The antioxidant activity of the α-piceid isomers, examined by radical scavenging capability, showed it to be initially lower than that of resveratrol, but as time passed, the α-piceid isomers' activity reached a level similar to that of resveratrol. The α-piceid isomers also showed better inhibitory activity against tyrosinase and melanin synthesis in B16F10 melanoma cells than β-piceid. The cellular uptake of the α-piceid isomers, which was assessed by ultra-performance liquid chromatography (UPLC) analysis of the cell-free extracts of B16F10 melanoma cells, demonstrated that the glycosylated form of resveratrol was gradually converted to resveratrol inside the cells. These results indicate that the enzymatic glycosylation of resveratrol could be a useful method for enhancing the bioavailability of resveratrol.

• Bulletin of the Korean Chemical Society
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• 제30권11호
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• pp.2769-2772
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• 2009

• 한국생물공학회:학술대회논문집
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• 한국생물공학회 2001년도 추계학술발표대회
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• pp.646-647
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• 2001

The enzymatic synthesis of conjugates of lysine and aspartic acid with D-glucose was studied. Optimase M-440 showed the very poor regioselectivity in the transesterification of $N{\alpha}$,$N'{\varepsilon}-di-t-Boc-L-Lys-OTFE$ and N-t-Boc-L-Asp-diOTFE with D-glucose. The acylation of glycosidic -OH and primary -OH of D-glucose occurred. However, Optimase M-440 catalyzed only the acylation of primary -OH group in the transesterification of $N{\alpha}$,$N'{\varepsilon}-di-t-Boc-L-Lys-OTFE$ and N-t-Boc-L-Asp-diOTFE with ${\alpha}-$ and ${\beta}-methylglucopyranoside$ in high yields without any other transesterification. Optimase M-440 also discriminated carboxyl groups of N-t-Boc-L-Asp-diOTFE.

• 한국생물공학회:학술대회논문집
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• 한국생물공학회 2005년도 생물공학의 동향(XVI)
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• pp.296-299
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• 2005

Sugar polymers have been considered as biomaterial. Biomaterials are widely utilized for a medical applications in direct contact with living tissue Clearly, biomaterials must be carefully and microscopically fabricated for optimal acceptance within the living organism in both functional and structural senses. In this study, the enzymatic synthesis of sorbitan methacrylate from 1,4-sorbitan via the manipulation of an immobilized biocatalyst (Novozym 435) and acryl donors (methacrylic acid and vinyl methacrylate) was evaluated.

• 한국안광학회지
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• 제5권1호
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• pp.89-94
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• 2000

메틸프록토시드 아크릴레이트와 메타크릴레이트를 효소적 배당화법으로 합성한 결과, 아크릴산과 메타크릴산의 배당화 전화율은 각각 78%나 93%이었으며, 연성콘택트렌즈용 의용고분자를 제조하기 위한 생체 친화성 단량체로서 활용될 것으로 기대된다.

• Journal of Microbiology and Biotechnology
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• 제18권1호
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• pp.107-109
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• 2008

Medicinal fungi, Phellinus linteus and Inonotus xeranticus, produce a cluster of yellow pigment in their fermentation broth that acts as an important element of biological activity. The pigment is composed of diverse polyphenols with a styrylpyrone moiety, mainly hispidin and its dimers, 3,14'-bihispidinyl, hypholomine B, and 1,1-distyrylpyrylethan. Although dimeric hispidins were proposed to be biosynthesized from two molecules of monomer via oxidative coupling by ligninolytic enzymes, laccase and peroxidase, the details of this process remain unknown. In this preliminary study, we attempted to achieve enzymatic synthesis of the hispidin dimer from hispidin by using commercially available horseradish peroxidase (HRP). Consequently, a hispidin dimer, 3,14'-bihispidinyl, was synthesized, whereas the other dimers, hypholomine B and 1,1-distyrylpyrylethan, were not produced. This result suggested that the oxidative coupling at the C-3 and C-14' positions of hispidins was dominant in the process of dimerization by HRP, and indicated that additional catalysts or substrates would be needed to synthesize other hispidin dimers present in the fungal metabolite.

• 대한안전경영과학회지
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• 제1권1호
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• pp.259-272
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• 1999

In order to enhance the selectivity, productivity and yield of methyl fructoside, which was synthesized by enzymatic glycosylation of sucrose and methanol solution, controlling of surface property of solid support using different immobilization procedures optimized microenvironment of immobilized invertase. Silanization and polyethylene imine coating methods were adopted to give a hydrophobic and hydrophilic environment of immobilized invertase. As a result, polyethyleneimine coating method gave higher loading of enzyme, effective activity, and relative activity than silanization method, because it brought on increasing the functional density of amino group and enhancing the conservation of activity by regulating of hydrophilicity. And then, hydrophilic environment was possible to restraint the assessing of methyl fructoside molecule, which was more hydrophobic than sucrose, fructose, and glucose molecule in the reaction mixture, into .the active site of immobilizedinvertase. Consequently, hydrophilic microenvironment of immobilized invertase by polyethyleneimine coating obtained higher yield and productivity with increasing conversion than silanized and native invertase. Thus, this procedure optimized the microenvironment of immobilized invertase suitable for the enzymatic synthesis of methyl fructoside.

• 한국생물공학회:학술대회논문집
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• 한국생물공학회 2003년도 생물공학의 동향(XII)
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• pp.459-459
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• 2003

• 공업화학
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• 제5권4호
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• pp.561-572
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• 1994

• Journal of Microbiology and Biotechnology
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• 제28권11호
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• pp.1859-1864
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• 2018

Synthesis of flavonoid glycoside is difficult due to diverse hydroxy groups in flavonoids and sugars. As such, enzymatic synthesis or biotransformation is an approach to solve this problem. In this report, we used stepwise biotransformation to synthesize two quercetin bisglycosides (quercetin 3-O-glucuronic acid 7-O-rhamnoside [Q-GR] and quercetin 3-O-arabinose 7-O-rhamnoside [Q-AR]) because quercetin O-rhamnosides contain antiviral activity. Two sequential enzymatic reactions were required to synthesize these flavonoid glycosides. We first synthesized quercetin 3-O-glucuronic acid [Q-G], and quercetin 3-O-arabinose [Q-A] from quercetin using E. coli harboring specific uridine diphopsphate glycosyltransferase (UGT) and genes for UDP-glucuronic acid and UDP-arabinose, respectively. With each quercetin 3-O-glycoside, rhamnosylation using E. coli harboring UGT and the gene for UDP-rhamnose was conducted. This approach resulted in the production of 44.8 mg/l Q-GR and 45.1 mg/l Q-AR. This stepwise synthesis could be applicable to synthesize various natural product derivatives in case that the final yield of product was low due to the multistep reaction in one cell or when sequential synthesis is necessary in order to reduce the synthesis of byproducts.