한국응용과학기술학회지 (Journal of the Korean Applied Science and Technology)

  • 제36권1호
  • /
  • Pages.84-89
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  • 2019
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  • 1225-9098(pISSN)
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  • 2288-1069(eISSN)
한국응용과학기술학회 (The Korean Society of Applied Science and Technology)
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베타-갈락토시데이즈를 이용하여 합성된 Benzyl Alcohol Galactoside의 NMR Spectroscopy 및 Mass spectrometry

NMR Spectroscopy and Mass Spectrometry of Benzyl Alcohol Galactoside synthesized using β-Galactosidase

  • 이향렬 (한국교통대학교 생명공학과) ;
  • 정경환 (한국교통대학교 생명공학과)
  • Lee, Hyang-Yeol (Department of Biotechnology, Korea National University of Transportation) ;
  • Jung, Kyung-Hwan (Department of Biotechnology, Korea National University of Transportation)
  • 투고 : 2019.03.08
  • 심사 : 2019.03.22
  • 발행 : 2019.03.31
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초록

대장균 효소 ${\beta}$-gal를 이용하여 합성된 BzO-gal의 분자구조를 NMR ($^1H$-와 $^{13}C$-)과 고성능 mass spectrometry를 이용하여 분석하였다. BzO-gal은 $^1H$ NMR에서 14개의 proton으로부터 12개의 피크를 나타내었다. 방향족 고리에서 오는 5개의 proton 피크와 벤질기의 $CH_2$에서 오는 2개의 proton 피크는 벤질알코올이 존재함을 나타낸다. 지방족 사슬 영역인 ${\delta}_H$ 4.32 ~ 3.46 ppm에서 나타나는 7개의 proton 피크로부터 단당류가 도입되었음을 확인할 수 있었다. $^{13}C$ NMR 스팩트럼에서 나타난 11개의 carbon 피크도 또한 벤질알코올에 단당이 도입되었음을 나타낸다. BzO-gal의 분자량을 확인하기 위하여 mass spectrometry 로 분석한 결과 m/z가 293.0994인 BzO-gal의 sodium adduct ion($[M+Na]^+$)을 확인할 수 있었다. 이러한 결과를 바탕으로 세포독성이 감소된 첨가물 개발을 기대하고 있으며, 추가적인 후속연구를 진행할 예정이다.

To characterize the molecular structure of BzO-gal synthesized using Escherichia coli ${\beta}$-gal, NMR ($^1H$- and $^{13}C$-) spectroscopy and mass spectrometry of BzO-gal were conducted. $^1H$ NMR spectrum of BzO-gal showed multiple peaks corresponding to the galactosyl group, which is an evidence of galactosylation on BzOH. Five proton peaks around the aromatic region at ${\delta}_H$ 7.43 ~ 7.24 ppm and 2 peaks from ${\delta}_H$ 4.93 and 4.67 ppm were evidence of the presence of the benzyl group. Seven proton peaks at ${\delta}_H$ 4.32 ~ 3.46 ppm showed the presence of a monosaccharide and were indicative of galactosylation on BzOH. $^{13}C$ NMR spectrum also revealed the presence of 11 carbons suggestive of BzO-gal. The mass value (sodium adduct ion of BzO-gal, m/z = 293.0994) from mass spectrometry analysis of BzO-gal, and $^1H$ and $^{13}C$ NMR spectral data were in good agreement with the expecting structure of BzO-gal. We are expecting that through future study it will eventually be able to develop a new additive of low cytotoxicity.

키워드

HGOHBI_2019_v36n1_84_f0001.png 이미지

Fig. 1. 1H-NMR spectrum of BzO-gal.

HGOHBI_2019_v36n1_84_f0002.png 이미지

Fig. 3. Mass spectrum of BzO-gal using ESI-MS. Arrow indicates a peak of sodium adduct ion of BzO-gal ([M+Na]+). In addition, molecular structure of [M+Na]+ is shown beside the arrow.

HGOHBI_2019_v36n1_84_f0003.png 이미지

Fig. 2. 13C-NMR spectrum of BzO-gal.

HGOHBI_2019_v36n1_84_f0004.png 이미지

Fig. 4. Transgalactosylation reaction of BzOH using β-gal.

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피인용 문헌

  1. 대장균 베타-갈락토시데이즈를 이용하여 합성된 Phenylethanol Galactoside의 NMR Spectroscopy 및 Mass spectrometry vol.37, pp.5, 2020, https://doi.org/10.12925/jkocs.2020.37.5.1323