Cysteine racemization in peptide synthesis: A new and easy detection method

Journal of Peptide Science

Volumn 2, Issue 4, 1996, Pages 271-275

  Siedler, Frank ^a   Weyher, Elisabeth ^a   Moroder, Luis ^a  

^a MAX PLANCK INSTITUTE OF BIOCHEMISTRY   (Germany)

Author keywords

Capillary electrophoresis; Cysteine; Enantiomeric resolution; Gas chromatography; Peptide synthesis; Racemization

Indexed keywords

CYSTEINE; PEPTIDE;

AMINO ACID SEQUENCE; ARTICLE; CHEMISTRY; HYDROLYSIS; MOLECULAR GENETICS; PROTEIN CONFORMATION; STEREOISOMERISM; SYNTHESIS;

AMINO ACID SEQUENCE; CYSTEINE; HYDROLYSIS; MOLECULAR SEQUENCE DATA; PEPTIDES; PROTEIN CONFORMATION; STEREOISOMERISM;

EID: 85047670173     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/psc.83     Document Type: Article

References (24)

1. G. B. Fields and R. L. Noble (1990). Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids. Int. J. Peptide Protein Res. 35, 161-214.
2. E. Atherton, N. L. Benoiton, E. Brown, R. C. Sheppard and B. J. Williams (1981). Racemization of activated, urethane-protected amino acids by pora-dimethylaminopyridine. Significance in solid-phase peptide synthesis. J. Chem. Soc. Chem. Commun. 336-337.
3. G. Adamson, T. Hoang, A. Crivici and G. A. Lajoie (1992). Use of Marfey's reagent to quantitate racemization upon anchoring of amino acids to solid supports for peptide synthesis. Anal. Biochem. 202, 210-214.
4. J. Kovacs, G. L. Mayers, R. H. Johnson. R. E. Cover and U. R. Ghatak (1970). Racemization of amino acid derivatives. Rate of racemization and peptide-bond formation of cysteine active esters. J. Org. Chem. 35, 1810-1815.
5. J. Kovacs, R. Cover, G. Jham, Y. Hsieh and T. Kalas in: Peptides: Chemistry, Structure and Biology, R. Walter and J. Meienhofer, Eds., p. 317-324, Ann Arbor Science Publ., Ann Arbor 1975.
6. E. Atherton, P. M. Hardy, D. E. Harris and B. H. Matthews in: Peptides 1990, E. Giralt and D. Andreu, Eds., p. 243-244, ESCOM, Leiden 1991.
7. Y. Fujiwara, K. Akaji and Y. Kiso in: Peptide Chemistry 1993, Y. Okada, Ed., p. 29-32, Protein Research Foundation, Osaka 1993.
8. H.-J. Musiol, F. Siedler, D. Quarzago and L. Moroder (1994). Redox-active bis-cysteinyl peptides. I. Synthesis of cyclic cystinyl peptides by conventional methods in solution and on solid supports. Biopolymers 34, 1553-1562.
9. H.-J. Musiol, D. Quarzago, R. Scharf and L. Moroder in: Peptides: Chemistry, Structure and Biology, R. S. Hodges and J. A. Smith, Eds., p. 62-64, ESCOM, Leiden 1994.
10. T. Kaiser, G. J. Nicholson and W. Voelter in: Peptides: Chemistry, Structure and Biology, P. T. P. Kaumaya, Ed., in press, ESCOM, Leiden 1996.
11. T. Kaiser, G. J. Nicholson, H. J. Kohlbau and W. Voelter (1995). Racemization of Fmoc-Cys(Trt)-OH during stepwise Fmoc-solid phase peptide synthesis. Tetrahedron Lett. 37, 1187-1190.
12. W. Woiwode, H. Frank, G. J. Nicholson and E. Bayer (1978). Racemisierungsstudien an cysteinhaltigen Peptiden. Chem. Ber. 111, 3711-3718.
13. H. Frank, W. Woiwode, G. J. Nicholson and E. Bayer (1981). Determination of the rate of acidic catalyzed racemization of protein amino acids. Liebigs Ann. Chem. 354-365.
14. J. A. Burns, J. C. Butler, J. Moran and G. M. Whitesides (1991). Selective reduction of disulfides by tris(2-carboxyethyl)phosphine. J. Org. Chem. 56, 2648-2650.
15. L. Moroder, M. Gemeiner, W. Goehring, E. Jaeger and E. Wünsch in: Peptides 1980, K. Brunfeldt, Ed., p. 121-126, Scriptor, Copenhagen, 1981.
16. H. Frank, G. J. Nicholson and E. Bayer (1978). Enantiomer labelling, a method for the quantitative analysis of amino acids. J. Chromatogr. 167, 187-196.
17. M. Friedman, L. H. Krull and J. F. Cavins (1970). Chromatographic determination of cysteine and cystine residues in proteins as S-β-(4-pyridylethyl)cysteine. J. Biol. Chem. 245, 3868-3872.
18. R. Kuhn, F. Erni, T. Bereuter and J. Häusler (1992). Chiral recognition and enantiomeric resolution based on host-guest complexatlon with crown ethers in capillary zone electrophoresis. Anal. Chem. 64, 2815-2820.
19. R. Kuhn, F. Stoecklin and F. Erni (1992). Chiral separation by host-guest complexation with cyclodextrin and crown ethers in capillary zone electrophoresis. Chromatographia 33, 32-36.
20. R. Kuhn and S. Hofstetter-Kuhn (1992). Chiral separation by capillary electrophoresis. Chromatographia 34, 505-512.
21. W. Lindner, B. Böhs and V. Seidel (1995). Enantioselective capillary electrophoresis of amino acid derivatives on cyclodextrin. Evaluation of structure-resolution relationships. J. Chromatogr. A 697, 549-560.
22. Y.-H. Lee and T. I. Lin (1995). Capillary electrophoretic determination of amino acids. Improvement by cyclodextrin additives. J. Chromatogr. A 716, 335-346.
23. N. Nimura, H. Ogura and T. Kinoshita (1980). Reversed-phase liquid chromatographic resolution of amino acid enantiomers by derivatization with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate. J. Chromatogr. 202, 375-379.
24. T. Kinoshita, Y. Kasahara and N. Nimura (1981). Reversed-phase high-performance liquid chromatographic resolution of non-esterified enantiomeric amino acid by derivatization with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate or 2,3,4-tri-O-acetyl-α-D-arabinopyranosyl isothiocyanate. J. Chromatogr. 210, 77-81.