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

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??

Keywords

References

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