• Journal of Microbiology and Biotechnology
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• 제32권5호
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• pp.657-662
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• 2022

Glycosyltransferase (GT)-specific degenerate PCR screening followed by in silico sequence analyses of the target clone was used to isolate a member of family1 GT-encoding genes from the established fosmid libraries of soil actinomycetes Micromonospora echinospora ATCC 27932. A recombinant MeUGT1 was heterologously expressed as a His-tagged protein in E. coli, and its enzymatic reaction with semi-synthetic phenoxodiol isoflavene (as a glycosyl acceptor) and uridine diphosphate-glucose (as a glycosyl donor) created two different glycol-attached products, thus revealing that MeUGT1 functions as an isoflavonoid glycosyltransferase with regional flexibility. Chromatographic separation of product glycosides followed by the instrumental analyses, clearly confirmed these previously unprecedented glycosides as phenoxodiol-4'-α-O-glucoside and phenoxodiol-7-α-O-glucoside, respectively. The antioxidant activities of the above glycosides are almost the same as that of parental phenoxodiol, whereas their anti-proliferative activities are all superior to that of cisplatin (the most common platinum chemotherapy drug) against two human carcinoma cells, ovarian SKOV-3 and prostate DU-145. In addition, they are more water-soluble than their parental aglycone, as well as remaining intractable to the simulated in vitro digestion test, hence demonstrating the pharmacological potential for the enhanced bio-accessibility of phenoxodiol glycosides. This is the first report on the microbial enzymatic biosynthesis of phenoxodiol glucosides.

• 통합자연과학논문집
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• 제8권1호
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• pp.48-55
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• 2015

Novel 2'(${\beta}$)-methyl-5'-deoxyapiose purine phosphonic acid analogues were designed and synthesized from 2-propanone-1,3-diacetate. Condensation successfully proceeded from a glycosyl donor 9 under Vorbr${\ddot{u}}$ggen conditions. Condensation of aldehyde 14 with Wittig reagent [(diethoxyphosphinyl)methylidene] triphenylphosphorane gave the desired nucleoside phosphonate analogues 15. Ammonolysis and hydrolysis of phosphonates gave the nucleoside phosphonic acid analogue 17 and 19. The synthesized nucleoside analogues were subjected to antiviral screening against HIV-1. The adenine analogue 19 exhibited weak in vitro activities against HIV-1.

• Journal of Microbiology and Biotechnology
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• 제8권6호
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• pp.710-713
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• 1998

A material with the same high performance liquid chromatography (HPLC) retention profile as authentic ascorbic acid 2-Ο-$\alpha$-glucoside (AA-2G) was detected in kimchi. This material was identified as AA-2G by testing its susceptibility to $\alpha$-glucosidase hydrolysis, the HPLC profile, and through the elementary analysis. Among several strains of bacteria isolated from fermented kimchi, four strains could produce cydodextrin glucanotransferase (CGTase) which catalyzes the transglucosylation reaction of ascorbic acid. By using starch as the glycosyl donor, AA-2G was produced as the major product through this reaction.

• 통합자연과학논문집
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• 제8권3호
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• pp.153-163
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• 2015

Racemic synthesis of novel 5',5'-difluoro-2'-methyl-apiose nucleoside phosphonic acid analogs was achieved as potent antiviral agents. Phosphonation was performed by direct displacement of triflate intermediate with diethyl (lithiodifluoromethyl) phosphonate to give the corresponding (${\alpha},{\alpha}$-difluoroalkyl) phosphonate. Condensation successfully proceeded from a glycosyl donor with persilylated bases to yield the nucleoside phosphonate analogs. Deprotection of diethyl phosphonates provided the target nucleoside analogs. An antiviral evaluation of the synthesized compounds against various viruses such as HIV, HSV-1, HSV-2 and HCMV revealed that the pyrimidine analogs (cytosine, uracil, and thymine) have weak anti-HIV or HCMV activity.

• Bulletin of the Korean Chemical Society
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• 제34권12호
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• pp.3621-3628
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• 2013

Novel 5'-deoxythreosyl purine phosphonic acid analogues containing a 2'-electropositive moiety such as fluorine atom, were designed and synthesized from commercially available 1,3-dihydroxy acetone. Condensation successfully proceeded from a glycosyl donor 6 under Vorbr$\ddot{u}$ggen conditions and cross-metathesis gave the desired phosphonate analogues 7a, 7b, 17a and 17b. The synthesized nucleoside phosphonic acid analogues 13, 16, 23, 26, 28 were subjected to antiviral screening against HIV-1. The bis(SATE) adenine analogue 28 exhibited significant in vitro activities against HIV-1.

• 통합자연과학논문집
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• 제8권2호
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• pp.99-106
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• 2015

Novel 2'(${\beta}$)-fluoro-3'(${\alpha}$)-hydroxy-threose nucleosides (iso-FMAU) as antiviral agents were designed and racemically synthesized from Solketal. Condensation successfully proceeded from a glycosyl donor 9 under $Vorbr{\ddot{u}}ggen$ conditions yielded the nucleoside analogues. Ammonolysis and hydrolysis of isopropylidene protection group gave the desired nucleoside analogues 12, 15, 18, and 19. The antiviral activities of the synthesized compounds were evaluated against the HIV-1, HSV-1, HSV-2 and HCMV. Compound 12 displayed some anti-HCMV activity ($EC_{50}=24.7{\mu}g/ml$) without exhibiting any cytotoxicity up to $100{\mu}M$.

• Journal of Microbiology and Biotechnology
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• 제16권1호
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• pp.64-67
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• 2006

To enhance the stability of ascorbic acid, the glycosylation of ascorbic acid was studied using the transfructosylation activity of levan fructotransferase. When levan was used as glycosyl donor, a novel fructoside (ascorbic acid 2-ffuctoside) was formed by the transfructosylation activity of the levan fructotransferase. The production of ascorbic acid 2-fructoside was highly affected by the concentration of the fructosyl acceptor (ascorbic acid). When $35\%$ of ascorbic acid and $2\%$ of levan were incubated with LFTase of 0.5 unit/glevan at $37^{\circ}C$ for 85 h, a maximum 52 g/l of AA-2F was produced.

• Bulletin of the Korean Chemical Society
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• 제29권10호
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• pp.1977-1982
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• 2008

Novel bicyclo[3.1.0]hexanyl purine nucleoside analogues were synthesized as potential antiherpetic agents via a bicyclo[3.1.0]hexanol (${\pm}$)-8, which was prepared using a highly efficient carbenoid cycloaddition reaction. A highly diastereoselective reduction of ketone and a Mitsunobu reaction for the condensation of glycosyl donor (${\pm}$)-12 with 6-chloropurine were employed.

• Bulletin of the Korean Chemical Society
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• 제35권9호
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• pp.2649-2654
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• 2014

Synthesis of north-5'-methylbicyclo[3.1.0]hexyl adenine and hypoxanthine nucleosides with an ethenyl group at C3' position was successfully achieved by a highly facile method. Methylbicyclo[3.1.0]hexanone (${\pm}$)-7 with three contiguous chiral centers and its epimer (${\pm}$)-6 was remarkably simply constructed only by four steps involving a carbenoid insertion reaction in the presence of rhodium (II) acetate dimer as a metal catalyst, giving a correct relative stereochemistry of the generated three chiral centers. Due to steric hindrance from the concave face of the bicyclo[3.1.0]hexanone system, a Grignard reaction of (${\pm}$)-7 with ethenylmagnesium bromide showed exclusive diastereoselectivity towards the b-face. The Grignard reaction chemoselectively proceeded without reacting with ester functionality. Coupling reaction of glycosyl donor (${\pm}$)-11 with 6-chloropurine nucleobase afforded only the desired $N^9$-alkylated nucleoside without the formation of $N^7$-regioisomer. By the conventional method, 6-chloro group was converted into 6-amino and 6-hydroxy groups to give the desired adenine and hypoxanthine bicyclo[3.1.0]hexyl carbanucleosides with 3'-ethenyl group, respectively.

• 한국약용작물학회지
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• 제13권5호
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• pp.276-283
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• 2005

Ascorbic acid is a great antioxidant and helps protect the body against pollutants. GDP-mannose pyrophosphorylase (GMPase) is a key enzyme in manufacturing GDP-mannose, a glycosyl donor for ascorbate and cell wall biosynthesis as well as for protein glycosylation. In this study, we described molecular cloning of a full-length cDNA from Potato (Solanum tuberosum L. cv. Jasim), using tuber. The cDNA isolated encoded a GDP-mannose pyrophosphrylase. The nucleotide sequence of pGMPC showed about 95%, 89% and 80% homology with S. tuberosum (AF022716), N. tabacum (AB066279) and A. thaliana (AF076484) cDNAs clone known as GMPase, respectively. We detected the expression of GMPase using RT-PCR. The highest expression of GMPase was found in stems, and the largest amount of ascorbic acid was also presented in stems. In contrast, the leaf showed minimal level of GMPase transcript and ascorbic acid content. We propose that GMPase expression patterns were similar to the changes of ascorbic acid content in the leaves treated with diverse stresses.