Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Synthesis and Characterization of N-Methylamidinoglycine : an Isomer of Creatine

N-Methylamidinoglycine의 합성 및 동정 Creatine의 이성질체

  • Young-Bong Cho (Wonju Medical School, Yonsei University) ;
  • R. John Stedman (School of Pharmacy, Temple University) ;
  • Woon Ki Paik (Fels Research Institute, Temple University School of Medicine)
  • 조영봉 (연세대학교 원주의과대학) ;
  • ;
  • 백운기 (미국 템플대학교 의과대학 헬스연구소)
  • Published : 1985.08.20
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Abstract

N-Methylamidinoglycine, an isomer of creatine which was postulated to be formed enzymatically in vitro, has been synthesized by coupling glycine with N, S-dimethylthiopseudouronium iodide in a yield of approxirnately 60%. On heating in acidic solution, it was converted to a cyclized form (isocreatinine) in analogy with the conversion of creatine to creatinine(anhydrous form). Structures were confirmed by an elemental analysis and proton NMR spectroscopy. Further studies on their characteristics were compared with those of creatine and creatinine in regard to isoelectric points(pI), retardation coefficients(Rf) on thin layer chromatography, and elution profiles on amino acid analyzer. In order to facilitate the comparison, $^{14}C$-labeled creatine, creatinine, isocreatine and isocreatinine were also synthesized.

시험관내에서 효소에 의해 생성될 수 있을 것으로 생각되는 N-Methylamidinoglycine(isocreatine)을 glycine과 N, S-dimethylthiopseudouronium iodide로 부터 약 60% 수득율로 합성하였고, isocreation의 산성수용액을 가열하여, creatine이 creatinine으로 탈수 고리화되는 것처럼, 고리화된 isocreatinine도 얻었다. 한편 이들 화합물에 대해 원소분석, nmr 스펙트럼, 박층 크로마토그피(Rf) 및 아미노산분석기에서의 elution rate도 검토하였으며, 등전점을 측정하기 위해서 $^{14}C$-creatine, $^{14}C$-creatinine, $^{14}C$-isocreatine 및 $^{14}C$-isocreatinine도 합성하였다.

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References

  1. J. Biol. Chem. v.249 Story, K.B.;Hochachka, P.W.
  2. J. Biol. Chem. v.249 McGilvery, R.W.;Murray, T.W.
  3. Biochim. Biophys. Acta v.81 Walker, J.B.;Wang, S.H.
  4. J. Cell Biol. v.63 Ingwall, J.S.;Weiner, C.D.;Morales, M.F.;Davis, E.;Stockdale, F.E.
  5. J. Mol. Cell. Cardiol. v.6 Seraydarian, F.W.;Artaza, L.;Abbott, B.C.
  6. Biochim. Biophys. Acta v.291 Scholte, H.R;Weijers, P.J.;Wit-Peeters, E.M.
  7. J. Biol. Chem. v.248 Jacobus, W.E.;Lehninger, A.L.
  8. Principles of Biochemistry Lehninger, A.L.
  9. Biochem. J. v.154 McDermott, J.R.
  10. Protein Methylation Paik, W.K.;Kim, S.
  11. J. Neurochem. v.34 Woznicki, D.T.;Walker, J.B.
  12. J. Am. Chem. Soc. v.93 Rowley, G. L.;Greenleaf, A. L.;Kenyon, G. L.
  13. J. Labeled Compounds Radiopharm. v.18 Abou-Gharbia, M.;Paik, W.K.;Swern, D.
  14. J. Org. Chem. v.39 Wang, T.
  15. Electrophoresis v.4 Farooqui, J.;Kim, S.;Paik, W.K.
  16. Biochemistry of S-Adenosylme-thionine and Related Compounds Cantoni, G.L.
  17. J. Biol. Chem. v.243 Paik, W.K.;Kim, S.