TRIFLUOROACETYL AMINO-PROTECTIVE GROUP IN SYNTHESIS OF L-ALANYLL-GLUTAMIC ACID AND L-α,γ-GLUTAMYL-BIS(L-ALANINE)
Abstract
N-Trifluoroacetyl-L-alanyl-L-glutamic acid dimethyl ester and N-trifluoroacetyl-L-α,γ-glutamyl-bis(methoxy-L-alanine) were obtained by condensation of N-trifluoroacetyl-L-alanine with L-glutamic acid dimethyl ester and N-trifluoroacetyl-L-glutamic acid with L-alanine methyl ester, respectively. Removal of protecting groups by sodium hydroxide in the compounds obtained and subsequent acidification of the reaction mixtures led to the formation of L-alanylL-glutamic acid and L-α,γ-glutamyl-bis(L-alanine). N-Trifluoroacetyl-L-alanine and N-trifluoroacetyl-L-glutamic acid were obtained from L-alanine and L-glutamic acid sodium salts using ethyl trifluoroacetate as an acetylating agent.
About the Authors
L. A. PopovaBelarus
Senior Researcher
13, Surganov Str., 220072
Z. P. Zubreichuk
Belarus
Senior Researcher
13, Surganov Str., 220072
V. A. Knizhnikov
Belarus
D. Sc. (Chemistry), Head of the Laboratory
13, Surganov Str., 220072
References
1. Sachs H., Brand E., “Optical Rotation of Peptides. VII. α- and γ-Dipeptides of Glutamic Acid and Alanine”, Journal of the American Chemical Society, 1953, vol. 75, no. 18, pp. 4608–4610.
2. Sachs H., Brand E., “Optical Rotation of Peptides. VIII. Glutamic Acid Tripeptides”, Journal of the American Chemical Society, 1954, vol. 76, no. 7, pp. 1811–1814.
3. Weygand F., Csendes E., “N-Trifluoracetyl-aminosäuren”, Angewandte Chemie, 1951, vol. 64, no. 5, p. 136.
4. Fones W. S., “Some new N-acyl derivatives of alanine and phenylalanine”, Journal of Organic Chemistry, 1952, vol. 17, no. 12, pp. 1661–1665.
5. Shine H. J., Niemann C., “The kinetics of the α-chymotrypsin-catalyzed hydrolysis of chloroacetyl- and trifluoroacetyl-L-tyrosinamide in aqueous solutions at 25o”, Journal of the American Chemical Society, 1952, vol. 74, no. 1, pp. 97–101.
6. Weygand F., Geiger R., “N-Trifluoracetyl-aminosauren. IV. Mitteil.: N-Trifluoracetylierung von ami-nosäuren in wasserfreier trifluoressigsäure”, Chemische Berichte, 1956, vol. 89, no. 3, pp. 647–652.
7. Weygand F., “N-Trifluoracetylaminosäuren. II. Mitteil”, Chemische Berichte, 1954, vol. 87, no. 2, pp. 248–256.
8. Fones W. S., Lee M., “Hydrolysis of the N-trifluoroacetyl derivatives of several D- and L- amino acids by acylase I”, Journal of Biological Chemistry, 1954, vol. 210, pp. 227–238.
9. Kricheldorf H. R., Fehrle M., “Herstellung von N-Trifluoroacetylaminosäuren und deren trimethylsilylestern”, Synthesis, 1974, no. 6, pp. 420–422.
10. Weygand F., Rinno H., “N-Trifluoracetyl-aminosäuren, XIII. Serin- und threonin-verbindungen”, Chemische Berichte, 1959, vol. 92, no. 3, pp. 517–527.
11. Schallenberg E. E., Calvin M., “Ethyl thioltrifluoroacetate as an scetylating agent with particular reference to peptide synthesis”, Journal of the American Chemical Society, 1955, vol. 77, no. 10, pp. 2779–2783.
12. Turaev O. D., Mar’yash L. I., Burichenko V. K., Shibev V. A., “Synthesis of trifluoroacetyl derivatives of oligopeptides forming analogs of the phosphorylatable section 33–40 of histone H1”, Chemistry of Natural Compounds, 1981, vol. 16, no. 4, pp. 394–397.
13. Panetta C. A., Casanova T. G., “Trifluoroacetylation of amino acids and peptides under neutral conditions”, Journal of Organic Chemistry, 1970, vol. 36, no. 12, pp. 4275–4277.
14. Weygand F., Röpsch A., “N-Trifluoracetyl-aminosäuren, XIV. N-Trifluoracetylierungen von aminosauren und peptiden mit trifluoressigsäure-phenylester”, Chemische Berichte, 1959, vol. 92, no. 9, pp. 2095–2099.
15. Bodanszky M., Fagan D. T., “Synthesis of biocytin-containing peptides”, Journal of the American Chemical Society, 1977, vol. 99, no. 1, pp. 235–239.
16. Preston J., Weinstein B., “Trifluoroacetyl as a protecting group for amino acid hydrazides”, Cellular and Molecular Life Sciences, 1967, vol. 23, no. 4, pp. 265–266.
17. Steglich W., Hinze S., “Eine rationelle synthese von N-trifluoroacetylaminosäuren”, Synthesis, 1976, no. 6, pp. 399–401.
18. Curphey T. J., Daniel D. S., “New synthesis of azaserine”, Journal of Organic Chemistry, 1978, vol. 43, no. 24, pp. 4666–4668.
19. Curphey T. J., “Trifluoroacetylation of amino acids and peptides by ethyl trifluoroacetate”, Journal of Organic Chemistry, 1979, vol. 44, no. 15, pp. 2805–2807.
20. Rosso V. W., Pazdan J. L., Venit J. J., “Rapid optimization of the hydrolysis of N’-trifluoroacetyl-S-tert-leucine-Nmethylamide using high-throughput chemical development techniques”, Organic Process Research & Development, 2001, vol. 5, no. 3, pp. 294–298.
21. Wyeth P., Sharma R. P., Akhtar M., “A proton-magnetic-resonance study of N-trifluoroacetyl-L-alanyl-L-phenylalaninal binding to α-chymotrypsin”, European Journal of Biochemistry, 1980, vol. 105, no. 3, pp. 581–585.
22. Blacklock T. J., Shuman R. F., Butcher J. W., Shearin Jr. W. E., Budavari J., Grenda V. J., “Synthesis of semisynthetic dipeptides using N-carboxyanhydrides and chiral induction on Raney nickel. A method practical for large scale”, Journal of Organic Chemistry, 1988, vol. 53, no. 4, pp. 836–844.
23. Jass P. A., Rosso V. W., Racha S., Soundararajan N., Venit J. J., Rusowicz A., Swaminathan S., Livshitz J., Delaney E. J., “Use of N-trifluoroacetyl-protected amino acid chlorides in peptide coupling reactions with virtually complete preservation of stereochemistry”, Tetrahedron, 2003, vol. 59, no. 45, pp. 9019–9029.
24. Ueda Y., Manabe H., Mitsuda M., Kitamura M., “On the production of Nε-trifluoroacetyl-L-lysine”, Oil and Natural Gas Production, 2000, vol. 78, no. 5, pp. 756–762.
25. Cherevin M. S., Gulevich T. G., Zubreichuk Z. P., Knizhnikov V. A., “Co-production of mono- and bis-trifluoroacetyl lysine”, Vestsі Natsyyanal’nai akademіі navuk Belarusі. Seryia khіmіchnykh navuk [Proceedings of the National Academy of Sciences of Belarus. Chemical Series], 2006, no. 4, pp. 71–74.
26. Cherevin M. S., Gulevich T. G., Popova L. A., Zubreichuk Z. P., Knizhnikov V. A., “N-Trifluoroacetyl-β-alanine in the synthesis of carnosine”, Zhurnal obshchei khimii [Russian Journal of General Chemistry], 2007, vol. 77, no. 9, pp. 1503–1507.
27. Cherevin M. S., Gulevich T. G., Popova L. A., Zubreichuk Z. P., Knizhnikov V. A., “Synthesis of γ-glutamyltryptophan derivatives”, Vestsі Natsyyanal’nai akademіі navuk Belarusі. Seryia khіmіchnykh navuk [Proceedings of the National Academy of Sciences of Belarus. Chemical Series], 2008, no. 1, pp. 57–63.
28. Cherevin M. S., Gulevich T. G., Iurashevich N. Ia., Zubreichuk Z. P., Knizhnikov V. A., “Synthesis of threonyl threonine”, Vestsі Natsyyanal’nai akademіі navuk Belarusі. Seryia khіmіchnykh navuk [Proceedings of the National Academy of Sciences of Belarus. Chemical Series], 2008, no. 2, pp. 52–55.
29. Cherevin M. S., Gulevich T. G., Popova L. A., Zubreichuk Z. P., Knizhnikov V. A., “N-trifluoroacyl derivatives of lysine in the synthesis of L-lysyl-L-glutamic acid”, Zhurnal organicheskoi khimii [Russian Journal of Organic Chemistry], 2007, vol. 43, no. 10, pp. 1437–1441.
30. Brenner M., Huber W., “Herstellung von α-Aminosäureestern durch Alkoholyse der Methylester”, Helvetica Chimica Acta, 1953, Bd. 36, no. 5, pp. 1109–1115.