Fmoc amino acid fluorides in peptide synthesis - Extension of the method to extremely hindered amino acids

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5483-5486

  Wenschuh, Holger ^a,b   Beyermann, Michael ^a   Winter, Rüdiger ^a   Bienert, Michael ^a   Ionescu, Dumitru ^c   Carpino, Louis A ^c  

^a LEIBNIZ INSTITUT FÜR MOLEKULARE PHARMAKOLOGIE   (Germany)

^b MAX PLANCK INSTITUTE FOR INFECTION BIOLOGY   (Germany)

^c UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; PEPTIDE SYNTHESIS; TECHNIQUE;

EID: 0030605880     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01160-4     Document Type: Article

References (13)

1. 1. a.) L.A. Carpino, D. Sadat-Aalaee, H.G. Chao, R.H. DeSelms, J. Am. Chem. Soc. 1990, 112, 9651.
2. b.) J.-N. Bertho, A. Loffet, C. Pinel, F. Reuther, G. Sennyey, Tetrahedron Lett. 1991, 32, 1303.
3. 2. D. Granitza, M. Beyermann, H. Wenschuh, H. Haber, L.A. Carpino, G.A. Truran, M. Bienert, J. Chem. Soc. Chem. Commun. 1995, 2223.
4. 3. H. Wenschuh, M. Beyermann, E. Krause, M. Brudel, R. Winter, M. Schümann, L.A. Carpino, M. Bienert, J. Org. Chem. 1994, 59, 3275.
5. 4. H. Wenschuh, M. Beyermann, H. Haber, J.K. Seydel, E. Krause, M. Bienert, L.A. Carpino, A. El-Faham, F. Albericio, J. Org. Chem. 1995, 60, 405.
6. +.
7. 6. P.G. Sammes, D.J. Weller Synthesis 1995, 1205.
8. 7. H. Wenschuh, M. Beyermann, A. El-Faham, S. Ghassemi, L.A. Carpino, M. Bienert, J. Chem. Soc. Chem. Commun. 1995, 669.
9. +.
10. 9. S. Rajeswari, R.J. Jones, M. P. Cava, Tetrahedron Letters 1987, 28, 5099. Because Fmoc amino acid fluorides of α,α-disubstituted amino acids suffer ready conversion to the corresponding oxazolones in the presence of fluoride ion acting as base the Cava methodology is not viable for the systems under study. On the other hand an in situ process involving BSA and believed to be initiated by silylation of the amino acid ester leads to increased reactivity. Mechanistic aspects of this reactivity enhancement are under investigation.
11. 10. H.-O. Kim, B. Gardner, M. Kahn, Tetrahedron Letters 1995, 36, 6013.
12. 3). reference line: TMS 0 ppm.
13. 12. J.R. Spencer, V.V. Antonenko, N. G.J. Delaet, M. Goodman Int. J. Pept. Prot. Res. 1992, 40, 282.