Conclusions
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1.
Four optically-active dipeptides of L-histidine containing di-(2-chloroethyl)amino groups have been synthesized: the methyl esters of p-di-(2-chloroethyl)aminophenylacetyl-L-histidyl-L-leucine, of p-di-(2-chloroethyl)aminophenylacetyl-L-leucyl-L-histidine, of p-di-(2-chloroethyl)aminophenylacetyl-L-histidyl-L-histidine, and of p-di-(2-chloroethyl)aminophenylacetyl-L-histidyl-L-methionine.
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2.
The methyl esters of the dipeptide p-di-(2-chloroethyl)aminophenylacetyl-L-histidyl-L-leucine synthesized by the azide method and by the p-nitrophenyl ester method had the same angles of optical rotation as the same dipeptide obtained by using the 1,3-dicyclohexylcarbodiimide method alone.
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3.
The condensations of p-di-(2-chloroethyl)aminophenylacetyl-L-histidine with the methyl esters of L-leucine, L-histidine, and L-methionine with the aid of 1,3-dicyclohexylcarbodiimide were carried out in dimethyl sulfoxide with no protection of the imidazole ring of the histidine.
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Literature cited
I. L. Knunyants, N. E. Golubeva, and O. V. Kil'disheva, Uspekhi Sovr. Biologii,50, No. 2(5), 167 (1960).
P'an Ch'i-ts'ao, Voprosy Onkologii,6, No. 10, 59 (1960).
N. C. Davis, J. Biol. Chem.,223, 935 (1956).
M. Brenner and W. Huber, Helv. Chim. Acta,36, 1109 (1953).
W. Y. Humphlett and C. V. Wilson, J. Org. Chem.,26, 2510 (1961).
M. Brenner and R. W. Pfister, Helv. Chim. Acta,34, 2085 (1951).
M. I. Dagene, L. P. Rasteikene, O. V. Kil'disheva, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim.,1969, 1822.
R. W. Holley and E. Sondheimer, J. Amer. Chem. Soc.,76, 1326 (1954).
C. D. Hurd and C. W. Bennett, J. Amer. Chem. Soc.,51, 265 (1929).
F. Schneider, Z. Physiol. Chem.,320, 82 (1960).
D. A. Dzhyuvene and Yu. A. Degutis, Subjects of the 10th Scientific Meeting of the Scientific-Research Institute for Oncology of the Lithuanian SSR [in Russian], Vilnius (1967), p. 27.
M. Fling, H. Wax, and C. W. Pettinga, J. Amer. Chem. Soc.,72, 1862 (1950).
H. A. Florsheim, S. Makineni, and S. Shankman, Arch. Biochem. Biophys.,97, 243 (1962).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1614–1618, July, 1970.
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Dagene, M.I., Rasteikene, L.P., Kil'disheva, O.V. et al. Carcinolytic peptides. Russ Chem Bull 19, 1517–1520 (1970). https://doi.org/10.1007/BF00853847
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DOI: https://doi.org/10.1007/BF00853847