Racemization test

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In peptide chemistry, a racemization test allows the quality of a coupling reaction and the steric uniformity of the synthesized peptide to be assessed.

There are a large number of racemization analyzes described, without one being considered to be the ideal test method for all systems. The known chemical test methods are based on the investigation of selected model peptides. A generalization of the test results obtained for a coupling method to all peptides is problematic because of the large number of peptide sequences based on the 20 proteinogenic amino acids . "In the absence of better methods, a new linking method should therefore be tested on different model systems."

Test methods (selection)

  • Anderson-Callahan test, synthesis of a model peptide and subsequent separation of stereoisomers by fractional crystallization
  • Young's test, a polarimetric method
  • Kemp test based on the principle of the isotope dilution technique
  • Weygand test, gas chromatographic separation of diastereomeric N α -trifluoroacetyl dipeptide methyl esters
  • Izumiya test
  • Bodanszky test
  • Halpern-Weinstein test
  • Berger-Schechter-Bosshard test
  • Fujino test

Individual evidence

  1. ↑ Hans-Dieter Jakubke, Hans Jeschkeit: Amino acids, peptides, proteins. Verlag Chemie, Weinheim 1982, ISBN 3-527-25892-2 , pp. 200-204.
  2. ↑ George W. Anderson, Francis M. Callahan: Racemization by the dicyclohexylcarbodiimide method of peptide synthesis . In: Journal of the American Chemical Society . tape 80 , no. 11 , June 1, 1958, pp. 2902–2903 , doi : 10.1021 / ja01544a077 .
  3. ^ MW Williams, GT Young: Amino-acids and peptides. Part XVI. Further studies of racemization during peptide synthesis . In: Journal of the Chemical Society (Resumed) . No. 0 , January 1, 1963, p. 881-889 , doi : 10.1039 / JR9630000881 .
  4. ^ Daniel S. Kemp, SW Wang, G. Busby, G. Hugel: Microanalysis by successive isotopic dilution. New assay for racemic content . In: Journal of the American Chemical Society . tape 92 , no. 4 , February 1, 1970, p. 1043-1055 , doi : 10.1021 / ja00707a051 .
  5. ^ Daniel S. Kemp, Julius Rebek: Peptide racemization mechanism. Kinetic isotope effect as a means of distinguishing enolization from oxazolone formation . In: Journal of the American Chemical Society . tape 92 , no. 19 , September 1, 1970, pp. 5792-5793 , doi : 10.1021 / ja00722a071 .
  6. ↑ F. Weygand, A. Prox, L. Schmidhammer, W. König: Gas chromatographic investigation of the racemization in peptide syntheses . In: Angewandte Chemie . tape 75 , no. 6 , 1963, pp. 282-287 , doi : 10.1002 / anie.19630750604 .
  7. ↑ Nobuo Izumiya, Masako Muraoka: Racemization test in peptide synthesis . In: Journal of the American Chemical Society . tape 91 , no. 9 , April 1, 1969, p. 2391-2392 , doi : 10.1021 / ja01037a045 .
  8. ↑ Miklos Bodanszky, Lois E. Conklin: A simple method for the study of racemization in peptide synthesis . In: Chemical Communications (London) . No. 15 , January 1, 1967, p. 773-774 , doi : 10.1039 / C19670000773 .
  9. ^ B. Halpern, DE Nitecki, B. Weinstein: The steric purity of model peptides by NMR spectroscopy . In: Tetrahedron Letters . tape 8 , no. 32 , January 1967, p. 3075-3078 , doi : 10.1016 / S0040-4039 (00) 90918-3 .
  10. ↑ Hans Rudolf Bonsshard, Israel Schechter, Arieh Berger: A New Method for the Detection of Racemization during Peptide Synthesis: Stereoselective hydrolysis of diastereomeric peptides by leucine aminopeptidase . In: Helvetica Chimica Acta . tape 56 , no. 2 , 1973, p. 717–723 , doi : 10.1002 / hlca.19730560216 .
  11. ↑ Chieko Kitada, Masahiko Fujino: New Peptide Models for Studying Racemization . In: Chemical & Pharmaceutical Bulletin . tape 26 , no. 2 , 1978, p. 585–590 ( full text as PDF ).