Studies on separation of amino acids and related compounds. 3. Separation of diastereomers of leucyl dipeptides by ion-exchange chromatography.

A series of experiments on a column chromatography of Dowex 50 with ammonium acetate solvent systems as eluent was carried out in order to find optimal conditions for the separation of the diastereomers of leucylalanine, leucylvaline, leucylleucine and leucyltyrosine. The effects of pH concentration of the salt and alcohols in the solvent systems for the separation of the diastereomers were studied. Among many conditions tested, the change of pH in the solvent system afforded most remarkable influence for the separation; the order of elution of the diastereomers of the dipeptide was found to be inverted at near pH 5.0. On a preparative scale L-leucyl-DL-valine was successfully separated into the two diastereomers by using a fairly large column. Attempt to separate benzyloxycarbonyl-L-leucyl-DL-valine benzyl ester with a column of Sephadex LH-20 was described, also.

[1]  N. Izumiya,et al.  Studies of peptide antibiotics. X. Syntheses of cyclosemigramicidin S and gramicidin S. , 1967, Bulletin of the Chemical Society of Japan.

[2]  F. Weygand,et al.  Racemisierung bei Peptidsynthesen , 1966 .

[3]  T. Wieland,et al.  Über Peptidsynthesen, 31. Chromatographische Trennung einiger diastereomerer Dipeptide und Betrachtungen zur Konformation , 1965 .

[4]  H. Aoyagi,et al.  Factors Influencing the Separation of 4-Hydroxyproline Diastereomers by Ion-Exchange Chromatography , 1964 .

[5]  F. Neuhaus,et al.  The enzymatic synthesis of D-alanyl-D-alanine. I. Purification and properties of D-alanyl-D-alanine synthetase. , 1962, The Journal of biological chemistry.

[6]  B. Erlanger,et al.  Synthesis of Peptides Related to Gramicidin S. II.1The Decapeptide Containing D-Tyrosine Residues in Place of D-Phenylalanine2 , 1958 .

[7]  N. Izumiya,et al.  Studies on Diastereoisomeric α-Amino Acids and Corresponding α-Hydroxy Acids. VII. Influence of β-Configuration on Enzymic Susceptibility , 1956 .

[8]  E. L. Smith,et al.  The specificity of leucine aminopeptidase. III. Action on diastereoisomers. , 1952, The Journal of biological chemistry.

[9]  Emil L. Smith,et al.  Some Peptides and Peptide Derivatives Containing Leucine and Alanine , 1949 .

[10]  M. Bergmann,et al.  ON PROTEOLYTIC ENZYMES VII. THE SYNTHESIS OF PEPTIDES OF l-LYSINE AND THEIR BEHAVIOR WITH PAPAIN , 1935 .

[11]  V. Mutt,et al.  Use of "lipophilic" Sephadex in peptide synthesis. , 1966, Journal of chromatography.

[12]  J. Biernat,et al.  THE CHROMATOGRAPHIC SEPARATION OF DIASTEREOISOMERIC DIPEPTIDES. , 1964, Journal of chromatography.

[13]  M. Volini,et al.  A new approach to the separation and purification of peptides. , 1960, Biochimica et biophysica acta.

[14]  S. Blackburn,et al.  A new method for the examination of mixtures of diastereoisomeric peptides. , 1956, Biochimica et biophysica acta.