Summary
o-Acetylation of cyclo-his-ser and cyclo-histhr in acetic acid/acetanhydride proceeds via intermolecular, and in the case of 4-hydroxyethyl-imidazole via intramolecular, acyl transfer. The highest rate of acetylation is observed with 4-hydroxyethyl-imidazole, and the most effective catalyst in the case of intermolecular acyl transfer is imidazole; derivatives of imidazole are less effective. Derivatives and peptides of serine are generally more reactive than those of threonine.
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Literatur
F. Schneider, Hoppe-Seyler's Z.338, 131 (1964); dort weitere Literatur.
Th. Bruice undG. L. Schmir, J. Am. chem. Soc.79, 1663 (1957).
S. Hestrin, J. biol. Chem.180, 249 (1949).
G. S. Reddy, Leon Mandell undI. H. Goldstein, J. chem. Soc.1963, 1414.
F. Schneider, Hoppe-Seyler's Z.334, 26 (1964).
Th. Bruice undTh. Fife, J. Am. chem. Soc.83, 1124 (1961).
W. Reppe et al., Liebigs Ann.596, 1 (1955) und zwar p. 68.
J. R. Totter undW. J. Darby, Org. Synthesis24, 64 (1944).
E. Rothstein, J. chem. Soc.1949, 1968.
A. Neuberger, Biochem. J.32, 1452 (1938).
I. W. Cornforth undH. T. Huang, J. chem. Soc.1948, 1960.
F. Schneider, erscheint demnächst in Hoppe-Seyler's Z.
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Schneider, F. Geschwindigkeit der imidazolkatalysierten o-Acetylierung von Derivaten und Peptiden des Serins und Threonins. Experientia 21, 316–317 (1965). https://doi.org/10.1007/BF02144687
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DOI: https://doi.org/10.1007/BF02144687