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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 29, Number 4
JKCSEZ 29(4)
August 20, 1985 

Synthesis and Characterization of N-Methylamidinoglycine : an Isomer of Creatine

N-Methylamidinoglycine의 합성 및 동정 Creatine의 이성질체
Young-Bong Cho, R. John Stedman, Woon Ki Paik

조영봉, R. John Stedman, 백운기
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 14C-creatine, 14 creatinine, 14C-isocreatine 및 14C-isocreatinine도 합성하였다.

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, 14C-labeled creatine, creatinine, isocreatine and isocreatinine were also synthesized.

419 - 425
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