• Title/Summary/Keyword: 1D and 2D NMR

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Structure Determination of Sucrose by Acetylation and Acid Hydrolysis

  • Min, Hee-Jeong;Lee, Tae-Seong;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.42 no.2
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    • pp.183-192
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    • 2014
  • For the structure determination of D-(+)-sucrose, which consists of ${\alpha}$-D-(+)-glucose and ${\beta}$-D-(+)-fructose, it was acetylated with acetic anhydride and triethyl amine, pyridine, zinc chloride, and sodium acetate as catalysts. The acetylated D-(+)-sucrose was acid-hydrolyzed using sulfuric acid and sodium chloride in methanolic solution. The structures of the reaction products were determined by $^1H$-NMR and $^{13}C$-NMR spectra. The yield of the acetylation indicated the high value in zinc chloride as 70% in zinc chloride catalyst. The acid-hydrolyzed product of the acetylated D-(+)-sucrose, 2,3,4,6,1',3',4',6'-octa-O-acetyl-D-(+)-sucrose, gave 2,3,4,6-tetra-O-acetyl-${\beta}$-D-(+)-glucose and it suggests that the acetylated D-(+)-sucrose was rearranged through the formation of oxonium ion by mutarotation in the 2,3,4,6-tetra-O-acetyl-${\alpha}$-D-(+)-glucose moiety and through the ring opening in the 1',3',4',6'-tetra-O-acetyl-${\beta}$-D-(+)-fructose moiety.

Comparative analysis of glycerin in cosmetics by LC/MS and 1H NMR (LC/MS와 1H NMR을 이용한 화장품속의 글리세린 비교분석)

  • Park, Gyo-Beom;Park, Chan Jo;Lee, Sueg-Geun
    • Analytical Science and Technology
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    • v.20 no.5
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    • pp.400-405
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    • 2007
  • The comparative analysis of glycerin in cosmetic samples was carried out by LC/MS and $^1H$ NMR spectrometry. For the LC/MS analysis, aqueous solution was controlled in strong basic condition with sodium hydroxide, and benzoyl chloride was added to the solution for the derivatization of glycerin. The derivative was extracted using pentane and analyzed by the LC/MS. For the $^1H$ NMR analysis, sample was directly dissolved in $D_2O$ solvent without pretreatment. The quantitative analysis of glycerin was done by $^1H$ NMR ERETIC method. The analysis results of LC/MS and $^1H$ NMR showed that the calibration curves were a good linearity with $r^2=0.9991$ in the range of 0.1 to $10{\mu}g/mL$ and $r^2=1$ in the range of 25 to $500{\mu}g/mL$, respectively.

A New Flavonoid from Carrichtera annua

  • Shahat, Abdelaaty A.;Abdel-Shafeek, Khaled A.;Husseiny, Husseiny A.;Claeys, Magda;Apers, Sandra;Pieters, Luc
    • Natural Product Sciences
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    • v.12 no.3
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    • pp.122-124
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    • 2006
  • Three flavonoid glycosides, $kaempferol-3-O-{\alpha}-L-rhamnopyranosyl-(1\;{\rightarrow}\;6)-{\beta}$-D-glucopyranoside$ or kaempferol-3-O-rutinoside (1), $isorhamnetic-3-O-{\alpha}-L-rhamnopyranosyl-(16)-{\beta}-D-glucopyranoside$ or isorhamnetin-3-O-rutinoside (2), and $quercetin-3-O-{\beta}-D-glucopyranosyl-(1 ${\rightarrow}\;2)-{\beta}-L-arabinopyranoside$ 3, the latter one being a new compound, were isolated from the methanolic extract of the aerial parts of Carrichtera annua. Mass spectrometry and 1D and 2D NMR spectroscopy allowed establishing the structure of these compounds.

Construction of 1H-15N Double Resonance Solid-State NMR Probe for Membrane Proteins in Aligned Bicelles

  • Park, Tae-Joon;Kim, Ji-Sun;Um, Seung-Hoon;Kim, Yong-Ae
    • Bulletin of the Korean Chemical Society
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    • v.31 no.5
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    • pp.1187-1191
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    • 2010
  • $^1H-^{15}N$ heteronuclear dipolar coupling solid-state NMR experiments on lipid bilayer or bicelle samples are very useful for the structural studies of membrane proteins. However, to study these biological samples using solid-state NMR, a specific probe with high efficiency and high capability is required. In this paper, we describe the optimized design, construction, and efficiency of a 400 MHz wide-bore $^1H-^{15}N$ solid-state NMR probe with 5-mm solenoidal rf coil for high power, multi-pulse sequence experiments, such as 2D PISEMA or 2D SAMMY.

Application of multi dimensional NMR experiments to VBS RNAs of Yeast Saccaromyces cerevisiae virus

  • Chaejoon Cheong;Cheong, Hae-Kap;Yoo, Jun-Seok
    • Journal of the Korean Magnetic Resonance Society
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    • v.5 no.1
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    • pp.29-36
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    • 2001
  • The structures of two VBS (viral binding site) RNAs, SL1 and SL2, of Yeast Saccharomyces cerevisiae vims have been studied by 2D and 3D NMR experiments. VBSs play a crucial role in viral particle binding to the plus strand and packaging of the RNA. The secondary structures of the two VBS RNAs share a common feature of the stem-internal loop-stem-hairpin loop structure although the size of the internal loops of SL1 and SL2 differs. 2D experiments were sufficient for fill assignments of SL1. However, isotope labeling of the sample and multidimensional experiments were required for 28-nucleotide-long SL2 due to the spectral overlap. Several 3D HCCH experiments have accomplished full assignment of SL2 RNA.

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Spirostane-type steroidal saponin from Allium hookeri roots with mushroom tyrosinase inhibitory activity

  • Kim, Yun Na;Lee, Jae Sun;Ock, Kwang Ju;Jeong, Eun Ju
    • Journal of the Korean Magnetic Resonance Society
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    • v.23 no.4
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    • pp.87-92
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    • 2019
  • Allium hookeri (Liliaceae) has been received the increasing attention as a bioactive resource due to its potent biological activities including anti-oxidant, anti-obesity, anti-microbial and lipid-regulating activities. The beneficial effects of A. hookeri are known contributed from the high content of organosulfur compounds in A. hookeri. Though a variety of articles demonstrated that A. hookeri contains 'saponin' as a bioactive constituent, the scientific evidence to prove it was limited. In the present study, we have attempted to identify saponin contained in A. hookeri through chromatographic isolation and NMR spectroscopic methods. As a result, a spirostane-type steroidal saponin (1) has been successfully isolated from the methanolic extract of A. hookeri roots. The structure of 1 was elucidated by extensive 1D and 2D spectroscopic methods including 1H-NMR, 13C-NMR, 1H-1H COSY, HSQC, HMBC and NOESY; identified as (3β, 22R, 25S)-spirost-5-en-3yl O-6-deoxy-α-L-mannopyranosyl-(1→4)-O-6-deoxy-α-L-mannopyranosyl-(1→4)-O-[6-deoxy-α-L-mannopyranosyl-(1→2)]-β-D-gluco pyranoside. 1 showed the significant inhibitory activity on mushroom tyrosinase with IC50 values of 248.7 μM while the inhibition on alpha-glucosidase was not significant.

A new derivative of phorbaketals isolated from a Marine Sponge Phorbas species

  • Hwang, Buyng-Su;Yang, Cao;Rho, Jung-Rae
    • Journal of the Korean Magnetic Resonance Society
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    • v.15 no.2
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    • pp.128-136
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    • 2011
  • A new sesterterpenoid, phorbaketal derivative, was isolated from the marine sponge Phorbas species. Its planar structures was completely determined from a combination of extensive 1D and 2D NMR experiments and MS data, and also the stereochemistry on the chiral centers were established by the ROESY experiment and the comparison with the $^1H$ and $^{13}C$ chemical shifts of the known phorbaketal compounds. This compound 1 moderately showed cytotoxicity effect against hepatoma cancer HepG2 cell.

Tone Quality Improvement Algorithm using Intelligent Estimation of Noise Pattern (잡음 패턴의 지능적 추정을 통한 음질 개선 알고리즘)

  • Seo, Joung-Kook;Cha, Hyung-Tai
    • Journal of the Korean Institute of Intelligent Systems
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    • v.15 no.2
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    • pp.230-235
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    • 2005
  • In this paper, we propose an algorithm that improves a tone quality of a noisy audio signal in order to enhance a performance of perceptual filter using intelligent estimation of noise pattern from a band degraded by additive noise. The proposed method doesn't use the estimated noise which is obtained from silent range. Instead new estimated noise according to the power of signal and effect of noise variation is considered for each frame. So the noisy audio signal is enhanced by the method which controls a estimation of noise Pattern effectively in a noise corruption band. To show the performance of the proposed algorithm, various input signals which had a different signal-to-noise ratio(SNR) such as $5\cal{dB},\;10\cal{dB},\;15\cal{dB}\;and\;20\cal{dB}$ were used to test the proposed algorithm. we carry out SSNR and NMR of objective measurement and MOS test of subjective measurement. An approximate improvement of $7.4\cal{dB},\;6.8\cal{dB},\;5.7\cal{dB},\;5.1\cal{dB}$ in SSNR and $15.7\cal{dB},\;15.5\cal{dB},\;15.2\cal{dB},\;14.8\cal{dB}$ in NMR is achieved with the input signals, respectively. And we confirm the enhancement of tone quality in terms of mean opinion score(MOS) test which is result of subjective measurement.

Isolation and Antimicrobial Activity of Dichlororinated Bibenzyl Compound

  • Na, Young-Soon;Lee, Jae-Sook;Baek, Seung-Hwa
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.21 no.1
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    • pp.231-234
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    • 2007
  • Dichlororinated bibenzyl compound (4) has been isolated from the New Zealand liverwort. This compound was elucidated using 1D/2D-NMR and mass spectral method. The compound (3) inhibited the growth of the Gram positive bacterium Bacillus subtilis ATCC 19659, (2 mm inhibition zone and 2 mm inhibition zone at 30 ${\mu}$g/disc), Candida albicans ATCC 14053, (2 mm inhibition zone and 2 mm inhibition zone at 30 ${\mu}$g/disc), and the dermatophytic fungi Trichophyton mentagrophytes ATCC 28185, (12 mm inhibition zone at 30 ${\mu}$g/disc) and Cladosporium resinae ATCC 52833 (2 mm inhibition zone at 30 ${\mu}$g/disc). This bibenzyl compound (4) exhibited antimicrobial activity.

A Systematic NMR Determination of α-D-Glucooligosaccharides, Effect of Linkage Type, Anomeric Configuration and Combination of Different Linkages Type on 13C Chemical Shifts for the Determination of Unknown Isomaltooligosaccharides

  • Goffin, Dorothee;Bystricky, Peter;Shashkov, Alexander S.;Lynch, Mary;Hanon, Emilien;Paquot, Michel;Savage, Angela V.
    • Bulletin of the Korean Chemical Society
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    • v.30 no.11
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    • pp.2535-2541
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    • 2009
  • Prebiotic isomaltooligosaccharide preparations contain $\alpha$-D-glucooligosaccharides comprising isomaltooligosaccharides (IMOs) and non-prebiotic maltooligosaccharides (MOs). They are both glucose oligosaccharides characterized by their degree of polymerization (DP) value (from 2 to $\sim$10), linkages types and positions (IMOs: $\alpha$-(1$\rightarrow$2, 3, 6 and in a lower proportion internal 1$\rightarrow$4) linkages, MOs: α-(1$\rightarrow$4) linkages). Their structure is the key factor for their prebiotic potential. In order to determine and elucidate the exact structure of unknown IMOs and MOs, unambiguous assignments of $^{13}C$ and $^1H$ chemical shifts of commercial standards, representative of IMOs and MOs diversity, have been determined using optimized standard one and two-dimensional experiments such as $^1H$ NMR, $^{13}C$ NMR, APT and ${^1}H-{^1}H$ COSY, TOCSY, NOESY and <$^1H-{^{13}}C$ heteronuclear HSQC, HSQC-TOCSY, and HMBC. Here we point out the differential effect of substitution by a glucose residue at different positions on chemical shifts of anomeric as well as ring carbons together with the effect of the reducing end configuration for low DP oligosaccharides and diasteroisotopic effect for H-6 protons. From this study, structural $^{13}C$ specific spectral features can be identified as tools for structural analysis of isomaltooligosaccharides.