Journal of Nuclear Science, Engineering and Technology (JONSAT)
In cooperation with the Iranian Nuclear Society

Synthesis of the DL-[3H] Leucine

Document Type : Research Paper

Authors

H Matlobi
GH Shirvani
N Saemian
Abstract
Labelled organic compounds have been widely applied to solve the research problems in life, science and chemistry. The preparation of labelled compounds, with carbon-14 and tritium-3 are probably more extensively and variously used in compare with any other isotopes. These isotopes emit only beta-particle. In this paper the synthesis of DL [3H] Leucine which was prepared for the first time in Iran is described. This compound is used for diagnosis of talasemi disease. The synthetic pathway is achieved by using the condensation of methyl allyl chloridewith diethyl acetamido malonatein the presence of sodium ethoxid in ethanol .In the next step of the synthesis, the latter compound was hydrogenated with 3H2(g.) over the Adams catalyst in chloroform, which was produced ethyl 2-acetamido-2- carbetoxy -4-methyl pentanoate  with a yield of 100%. In final step, the resulted product was converted directly to [4,5-3H] Leucine with the specific activity 5 Ci/mmol, by reflaxing with the hydrobromic acid of 48%.

Highlights

References:

 

 

 

 

  1. a) C.L. Comar, Radioisotopes in Biology and Agriculture, Mc-Graw Hill , New York, 201 (1955).

    b) C.A. Sanjose, Nuclides and Isotopes, 14 (1989).

     

  2. a) A.Di. Luccia, L. Lannibelli, D. Ferranti, L. Manca, B. Masala, L. Ferrara, Biochem. Genet, 29, 421 (1991).

b) J.B. Clegg,  S.E.Y. Goodbourn, M. Braend, Nucleic acids Res, 12, 7847(1984).

 

  1. a) R. Galanello, S. Satta, M.G. Pirroni, M. Travi, L. Maccioni, J. Hemoglobin, 22, 501 (1998).

b) J. B. Clegg, The Thalassemias, edited by D.J. Weatherall, Churchill Livingstone, Edimburgh, 6, 54 (1983).

 

  1. a) M.D. Fryzuk, B. Bosnich, J. Am. Chem. Soc. 99, 6262 (1977).

b) J. Albertson and K. Archer J.Biol.Chem, 67, 308 (1945).

  1. A.J. Zambito and Eugene E. Howe, ORGANIC SYNTHESIS, CV5, 373 (2002).

     

  2. a) E.E. Reid, J.R. Ruhoff, ORGANIC SYNTHESIS, CV2, 474 (2002).

     b) M.J.Coon and S.Gurin . J.Biol.chem., 49, 1159 (1949).

     

  3. a) H.W. Thompson, E. Mcpherson, B.L. Lences, J. Org. Chem., 2903 (1976).

b) J. Done, P.R. payne, J. Biochem, 64, 268 (1959).

 

  1. a) G.B. Heisig, F.H. Stodola, ORGANIC SYNTHESIS, CV3, 213 (2002).

    ب)  ح. مطلـوبی، غ. شیروانی، ن. صائمیان، ”سنتـز لوسیـن نشـاندار با تریتیوم [H3]،“ سازمان انرژی اتمـی، گـزارش عـلمـی و فنـی شـماره RPD-LC-2002-SK-12 (اسفند سال 1380).

Keywords

tritium
leucine
talasemi
amino acids

  1. References:

     

     

     

     

    1. a) C.L. Comar, Radioisotopes in Biology and Agriculture, Mc-Graw Hill , New York, 201 (1955).

      b) C.A. Sanjose, Nuclides and Isotopes, 14 (1989).

       

    2. a) A.Di. Luccia, L. Lannibelli, D. Ferranti, L. Manca, B. Masala, L. Ferrara, Biochem. Genet, 29, 421 (1991).

    b) J.B. Clegg,  S.E.Y. Goodbourn, M. Braend, Nucleic acids Res, 12, 7847(1984).

     

    1. a) R. Galanello, S. Satta, M.G. Pirroni, M. Travi, L. Maccioni, J. Hemoglobin, 22, 501 (1998).

    b) J. B. Clegg, The Thalassemias, edited by D.J. Weatherall, Churchill Livingstone, Edimburgh, 6, 54 (1983).

     

    1. a) M.D. Fryzuk, B. Bosnich, J. Am. Chem. Soc. 99, 6262 (1977).

    b) J. Albertson and K. Archer J.Biol.Chem, 67, 308 (1945).

    1. A.J. Zambito and Eugene E. Howe, ORGANIC SYNTHESIS, CV5, 373 (2002).

       

    2. a) E.E. Reid, J.R. Ruhoff, ORGANIC SYNTHESIS, CV2, 474 (2002).

       b) M.J.Coon and S.Gurin . J.Biol.chem., 49, 1159 (1949).

       

    3. a) H.W. Thompson, E. Mcpherson, B.L. Lences, J. Org. Chem., 2903 (1976).

    b) J. Done, P.R. payne, J. Biochem, 64, 268 (1959).

     

    1. a) G.B. Heisig, F.H. Stodola, ORGANIC SYNTHESIS, CV3, 213 (2002).

      ب)  ح. مطلـوبی، غ. شیروانی، ن. صائمیان، ”سنتـز لوسیـن نشـاندار با تریتیوم [H3]،“ سازمان انرژی اتمـی، گـزارش عـلمـی و فنـی شـماره RPD-LC-2002-SK-12 (اسفند سال 1380).

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