Zinc-promoted simple synthesis of oligomer-free N(α)-Fmoc-amino acids using Fmoc-Cl as an acylating agent under neutral conditions

Journal of Peptide Research

Volumn 55, Issue 4, 2000, Pages 295-299

  Gopi, Hosahudya N ^a   Suresh Babu, Vommina V ^a  

^a BANGALORE UNIVERSITY   (India)

Author keywords

Activated zinc dust; Dipeptide contaminants; Fmoc function; Fmoc Cl; Neutral conditions; Schotten Baumann conditions

Indexed keywords

9 FLUORENYLMETHYL CHLOROFORMATE; AMINO ACID; ZINC;

ACYLATION; ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OLIGOMERIZATION; PRIORITY JOURNAL; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

ACYLATION; AMINO ACIDS; CARBAMATES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, THIN LAYER; FLUORENES; ZINC;

EID: 0034113883     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.2000.00668.x     Document Type: Article

References (26)

1. 1. Carpino, L.A. & Han, G.Y. (1970) The 9-fluorenylmethoxycarbonyl function, a new base-sensitive amino-protecting group. J. Am. Chem. Soc. 92, 5748-5749.
2. 2. Carpino, L.A. & Han, G.Y. (1972) The 9-fluorenylmethoxycarbonyl amino-protecting group. J. Org. Chem. 37, 3404-3409.
3. 3. Carpino, L.A. (1987) The 9-fluorenylmethyloxy carbonyl family of base-sensitive amino protecting groups. Acc. Chem. Res. 20, 401-407.
4. 4. Fields, G.B. & Noble, R.L. (1990) Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonylamino acids. Int. J. Peptide Protein Res. 35, 161-214.
5. 5. Gopi, H.N. & Suresh Babu, V.V. (1998) Synthesis of peptides employing Fmoc-amino acid chlorides and commercial zinc dust. Tetrahedron Lett. 39, 9769-9772.
6. 6. Ranu, B.C., Majee, A. & Dass, A.R. (1996) A convenient synthesis of β,γ-unsaturated ketones through zinc mediated allylation of acid chlorides. Tetrahedron Lett. 37, 1109-1112.
7. 7. Ranu, B.C., Majee, A. & Dass, A.R. (1995) Facile and efficient synthesis of homoallylic alcohols using allyl bromide and commercial zinc dust. Tetrahedron Lett. 36, 4885-4888.
8. 8. Meshram, H.M., Reddy, G.S., Reddy, M.M. & Yadav, J.S. (1998) Zinc mediated amide formation: application of alkyl, aryl, hetero cycle, carbohydrate and amino acids. Tetrahedron Lett. 39, 4103-4106.
9. 9. Meshram, H.M., Reddy, G.S., Reddy, M.M. & Yadav, J.S. (1998) Zinc promoted facile method for the acylation of ylides at α-carbon. Tetrahedron Lett. 39, 4107-4110.
10. 10. Yadav, J.S., Reddy, G.S., Reddy, M.M. & Meshram, H.M. (1998) Zinc promoted simple and convenient synthesis of carbamates: an easy access for amino group protection. Tetrahedron Lett. 39, 3259-3262.
11. 11. Bodanszky, M. & Bodanszky, M. (1984) The Practice of Peptide Synthesis. Springer-Verlag, Berlin, pp. 24-25.
12. 12. Atherton, E. & Sheppard, R.C. (1989) Solid Phase Peptide Synthesis. IRL Press, Oxford.
13. 13. Gutte, B. (1995) Peptides, Synthesis, Structures and Applications. Academic Press, San Diego.
14. 14. Jones, J. (1991) The Chemical Synthesis of Peptides. Clarendon Press, Oxford, pp. 17-22.
15. 15. Atherton, E. & Sheppard, R.C. (1987) The fluorenylmethoxycarbonyl amino protecting group. The Peptides, Vol. 9. (Udenfriend, S. & Meienhofer, J., eds). Academic Press Inc., San Diego, pp. 1-38.
16. 16. Tessier, M., Albericio, F., Pedroso, E., Grandas, A., Eritja, R., Giralt, E., Granier, C. & van Reitschoten, J. (1983) Amino acids condensations in the preparation of Nα-9-fluorenylmethyloxycarbonyl amino acids with 9-fluorenylmethyl chloroformate. Int. J. Peptide Protein Res. 22, 125-128.
17. 17. Sigler, G.F., Fuller, W.D., Chaturvedi, N.C., Goodman, M. & Verlander, M. (1983) Formation of oligopeptides during the synthesis of 9-fluorenylmethyloxy carhonyl amino acid derivatives. Biopolymers 22, 2157-2162.
18. 18. Benoiton, N.L., Chen, F.M.F., Steinauer, R. & Chouinard, M. (1986) General procedure for preparing a reference mixture and determining the amount of dipeptide contaminant in N-alkoxycarbonylamino acids by high-performance liquid chromatography. Int. J. Peptide Protein Res. 27, 28-33.
19. 19. Lapatsanis, L., Milias, G., Froussior, K. & Kolovos, M. (1983) Synthesis of 1,2,2,2-(trichloroethoxycarbonyl)-L-amino acids and N-(9-fluorenylmethoxycarbonyl)-L-amino acids involving succinimidoxy anion as a leaving group in amino protection. Synthesis, 671-673.
20. 20. Iguchi, S., Kawasaki, K. & Okada, Y. (1987) Amino acids peptides. Int. J. Peptide Protein Res. 30, 695-700.
21. 21. Paquet, A. (1982) Introduction of 9-fluorenylmethyloxycarbonyl, trichloroethoxycarbonyl and benzyloxycarbonyl amino protecting groups into O-unprotected hydroxyamino acids using succinimidyl carbamates. Can. J. Chem. 60, 976-980.
22. 22. Paul, B.W., Kortenaar, T., Dijk, B.G.V., Peeters, J.M., Raaben, B.J., Adams, P.J.H.M. & Tesser, G.I. (1986) Rapid and efficient method for the preparation of Fmoc-amino acids starting from 9-fluorenylmethanol. Int. J. Peptide Protein Res. 27, 398-400.
23. 23. Schon, I. & Kisfaludy, L. (1986) 9-Fluorenylmethyl pentafluorophenyl carbonate as a useful reagent for the preparation of N-9-fluorenylmethyloxycarbonyl amino acids and their pentafluorophenyl esters. Synthesis, 303-305.
24. 24. Barcelo, G., Senet, J.P. & Sennyey, G. (1986) Alkyl-1-chloroalkyl carbonates: reagents for the synthesis of carbamates and protection of amino groups. Synthesis, 627-632.
25. 25. Bolin, D.R., Sytwu, I.I., Humiee, F. & Meienhofer, J. (1989) Preparation of oligomer free Nα-Fmoc-and Nα-urethane amino acids. Int. J. Peptide Protein Res. 33, 353-359.
26. 26. Meienhofer, J. (1985). Chemistry and Biochemistry of the Amino Acids (Barrett, G.C., ed.). Chapman & Hall, London, pp. 297-337.