• Bulletin of the Korean Chemical Society
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• 제29권7호
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• pp.1315-1319
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• 2008

A trisaccharide, 6d-Altro-Hepp$\alpha$ (1$\rightarrow$3) GlcNAc$\beta$ (1$\rightarrow$3) Gal$\alpha$ (1$\rightarrow$$OCH_2CH_2N_3$, as an O-antigenic repeating unit of Campylobacter jejuni serotypes O:23 and O:36, was synthesized. Coupling of the 6d-altro-Hepp$\alpha$ (1$\rightarrow$3) GlcNAc$\beta$ (1$\rightarrow$SEt donor with Gal$\alpha$ (1${\rightarrow}OCH_2CH_2Cl$ acceptor in the presence of NIS-TfOH promoter afforded the trisaccharide having the $\beta$ (1$\rightarrow$3) Gal linkage. $\beta$ -Stereospecificity and the desired regioselectivity for the 3-OH Gal are obtained. Subsequent hydrogenation, acetylation, azide displacement, hydrazinolysis, Nacetylation, and finally deacetylation furnished the title trisaccharide hapten for further glycoconjugation.

• 한국식품과학회지
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• 제27권4호
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• pp.605-611
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• 1995

호남지방에서 생산된 6점의 토종꿀을 대상으로 disaccharides와 trisaccharides를 분취한 다음 GC와 HPLC를 이용하여 각 oligosaccharides를 분리, 정량하였다. disaccharides는 토종꿀 중에 $5.9{\sim}8.4%$ 범위로 함유되어 있었는데 GC로 분석한 결과 sucrose, nigerose, maltose, laminaribiose, turanose, kojibiose, palatinose 및 isomaltose 등 8개의 당류가 분리되었으며, 그 중 maltose가 평균 2.28%로 가장 많이 함유되어 있었으며 그 다음으로 turanose가 평균 1.57%의 함량을 나타냈다. trisaccharides는 토종꿀 중에 $1.4{\sim}5.4%$ 범위로 함유되어 있었는데 isopanose, erlose, theanderose, maltotriose, panose 등 5개의 당류가 분리되었으며, 그 중 erlose가 평균 2.83%로 가장 많은 부분을 차지하고 있었다. 토종꿀중에 함유되어 있는 전체 oligosaccharides의 조성을 살펴보면 erlose가 가장 많이 함유되어 있었으며 maltose, turanose, sucrose, isomaltose의 순서로 많이 함유되어 있었다.

• Bulletin of the Korean Chemical Society
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• 제25권2호
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• pp.289-292
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• 2004

A trisaccharide, GlcNAcp- ${\beta}-(1{\to}3)-Galp-{\alpha}-(1{\to}2)$-6-deoxy-altroHepp- ${\alpha}-(1{\to}O$-propyl, as an O-antigenic repeating unit of C. jejuni serotype O:23 and O:36 was synthesized. Coupling of the GlcNPhth-(1${\to}$3)-Gal disaccharide donor with allyl 6-deoxy-altroHep acceptor in the presence of iodonium dicollidine perchlorate (IDCP) promoter afforded the ${\alpha}$-galactosidic trisaccharide with high stereoselectivities. Subsequent deacetalation, dephthaloylation, N-acetylation, and hydrogenolytic debenzylation furnished the title compound.

• Archives of Pharmacal Research
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• 제27권2호
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• pp.143-150
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• 2004

A trisaccharide, the O-antigenic repeating unit of C. jejuni serotype O:23 and O:36, was synthesized as a 2 -azidoethyl glycoside by block addition of perbenzylated thiogalactoside donors to $\alpha$-altroHepp-(1$\rightarrow$3)-GlcNPhth disaccharide acceptor in presence of IDCP promoter. The $\alpha$-linked altroheptopyranoside moiety in the glycosyl acceptor was effectively prepared by Swern oxidation of $\alpha$-mannohepp-(1$\rightarrow$3)-GlcNPhth disaccharide followed by mild reduction with1 $NaCNBH_3$.

• Natural Product Sciences
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• 제13권3호
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• pp.225-228
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• 2007

A new quercetin 3-O-trisaccharide was isolated from the leaves of Rubus crataegifolius (Rosaceae). The structure of this compound was determined as quercetin $3-O-{\alpha}-L-arabinofuranosyl-(1{\rightarrow}2)-{\beta}-D-xylopyranosyl-(1{\rightarrow}2)-{\beta}-D-galactopyranoside$ on the basis of 2D-NMR spectroscopic data. This flavonol glycoside was isolated for the first time from a natural source.

• Food Science and Biotechnology
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• 제17권1호
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• pp.199-202
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• 2008

The effects of $\beta$-(1,6)-galactosyl trehalose trisaccharide ($\beta$-GT) that was preferentially produced by Escherichia coli $\beta$-galactosidase on cryo- and thermo-protections of protein were investigated with those of other sugars at the level of 8% (w/v). As compared to a control without sugar additive, $\beta$-GT effectively enhanced 32-54% of the cryoprotection of fish actomyosin against repeated freeze-thawing and frozen storage, and also 49% of the protection against thermal inactivation of pyrophosphatase, respectively. As a result, it was significantly more effective than sorbitol and trehalose in both cryoprotection and thermoprotection. Thus, $\beta$-GT would be possibly applied as a sugar substitute for cryo- and thermo-protective applications of food protein.

• Preventive Nutrition and Food Science
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• 제21권2호
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• pp.124-131
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• 2016

Among 116 bacterial strains isolated from Korean fermented foods, one strain (SS-76) was selected for producing new oligosaccharides in a basal medium containing maltose as the sole source of carbon. Upon morphological characterization using scanning electron microscopy, the cells of strain SS-76 appeared rod-shaped; subsequent 16S rRNA gene sequence analysis revealed that strain SS-76 was phylogenetically close to Bacillus subtilis. The main oligosaccharide fraction B extracted from the culture supernatant of B. subtilis SS-76 was purified by high performance liquid chromatography. Subsequent structural analysis revealed that this oligosaccharide consisted only of glucose, and methylation analysis indicated similar proportions of glucopyranosides in the 6-linkage, 4-linkage, and non-reducing terminal positions. Matrix-assisted laser-induced/ionization time-of-flight/mass spectrometry and electrospray ionization-based liquid chromatography-mass spectrometry/mass spectrometry analyses suggested that this oligosaccharide consisted of a trisaccharide unit with 1,6- and 1,4-glycosidic linkages. The anomeric signals in the $^1H$-nuclear magnetic resonance spectrum corresponded to ${\alpha}$-anomeric configurations, and the trisaccharide was finally identified as panose (${\alpha}$-D-glucopyranosyl-1,6-${\alpha}$-D-glucopyranosyl-1,4-D-glucose). These results suggest that B. subtilis SS-76 converts maltose into panose; strain SS-76 may thus find industrial application in the production of panose.

• Journal of Microbiology and Biotechnology
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• 제34권4호
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• pp.911-919
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• 2024

Solar UVB irradiation cause skin photoaging by inducing the high expression of matrix metalloproteinase (MMPs) to inhibit the expression of Type1 procollagen synthesis. 1-Kestose, a natural trisaccharide, has been indicated to show a cytoprotective role in UVB radiation-induced-HaCaT cells. However, few studies have confirmed the anti-aging effects. In the present study, we evaluated the anti-photoaging and pathological mechanism of 1-kestose using Human keratinocytes (HaCaT) cells. The results found that 1-kestose pretreatment remarkably reduced UVB-generated reactive oxygen species (ROS) accumulation in HaCaT cells. 1-Kestose suppressed UVB radiation-induced MMPs expressions by blocking MAPK/AP-1 and NF-κB p65 translocation. 1-Kestose pretreatment increased Type 1 procollagen gene expression levels by activating TGF-β/Smad signaling pathway. Taken together, our results demonstrate that 1-kestose may serve as a potent natural trisaccharide for inflammation and photoaging prevention.

• 대한화학회지
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• 제42권5호
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• pp.549-558
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• 1998

Campylobacter jejuni 그램 음성균의 O-antigen 부위를 구성하는 반복 단위 삼탄당 합성의 주요 중간체인 이당류들을 글루코스아민 주게와 갈락토스 받게를 ${\beta}(1{\rightarrow}3)$ 클리코시드 결합으로 연결함으로서 합성하였댜. 이들의 합성 과정에서 갈락토스 당 부위의 2, 3, 4 번 OH기들의 글루코스아민 받게에 대한 높은 위치선택성이 발견되었으며 이를 이용하여 2, 4번 OH에 대한 선택적 보호과정을 생략할 수 있었고 결과적으로 합성과정을 단축시킬 수 있었다.

• 한국약용작물학회지
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• 제17권1호
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• pp.61-67
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• 2009

This study carried out development of a natural antimicrobial agent from Schima wallichii ssp. liukiuensis. Compound I exhibiting potent antimicrobial activity against Candida spp. was isolated from the methanol extracts of Schima wallichii ssp. liukiuensis. The structure of I identified as a sterol glycoside consisted of a trisaccharide and ${\alpha}_1$-sitosterol. Trisaccharide composed of L-rhamnose, D-galactose and D-glucose residues. The antimicrobial activity of I was selective on yeast rather than bacteria or other fungi. Compound I was demonstrated to be ineffective against toxicity to mouse liver cells where as protective to human dermal fibroblast cells at low concentrations. Thus, it is reasonable to expect a sterol glycoside (I) as a valuable alternative for synthetic antifungal.