The development of solid phase protocols for a backbone amide linker and its application to the Boc-based assembly of linear peptides

Tetrahedron Letters

Volumn 40, Issue 40, 1999, Pages 7271-7274

  Bourne, Gregory T ^a   Meutermans, Wim D F ^a   Smythe, Mark L ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Peptide synthesis; Secondary amine acylation; Solid support

Indexed keywords

AMIDE; AMINE; PEPTIDE;

ACYLATION; ARTICLE; PEPTIDE SYNTHESIS; REACTION ANALYSIS; SOLID; STEREOSPECIFICITY;

EID: 0033215454     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01473-2     Document Type: Article

References (15)

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2. Jensen, K. L.; Songster, M. F.; Vágner, J.; Alsina, J.; Albericio, F.; Barany, G. In Peptides: Chemistry, Structure and Biology; (Proceedings of the 14th American Peptide Symposium); Kaumaya, P. T. P.; Hodges, R. S., Eds.; Mayflower Scientific: Kingswinford, UK, 1996; pp. 30-32.
3. Fresno, M.; Alsina, J.; Royo, M.; Barany, G.; Albericio, F. Tetrahedron Lett. 1998, 39, 2639-2642.
4. Bourne, G. T.; Meutermans, W. D. F.; Alewood, P. F.; McGeary, R. P.; Scanlon, M.; Watson, A. A.; Smythe, M. L. J. Org. Chem. 1999, 64, 3095-3101.
5. Schnölzer, M.; Alewood, P.; Jones, A.; Alewood, D.; Kent, S. B. H. Int. J. Pept. Protein Res. 1992, 40, 180-193.
6. 4. Volatiles were removed in vacuo and the resulting solid recrystallised (hexane:EtOAc, 1:1) to yield a yellow solid (18.2 g, 90%), mp 99-101°C.
7. Dockray, G. J.; Gregory, R. A.; Hutchinson, J. B.; Harris, J. I.; Runswick, M. J. Nature 1978, 274, 711-712.
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11. Kates, S. A.; Daniels, S. B.; Solé, N. A.; Barany, G.; Albericio, F. In Peptides, Chemistry, Structure and Biology; (Proceedings of the 13th American Peptide Symposium); Hodges, R. S.; Smith, J. A., Eds.; ESCOM: Leiden, The Netherlands, 1994; pp. 113-114.
12. CCK (25-33) Purified Yield: (20.0 mg, 52%); ES-MS Mr 1063.6 (calcd 1063.2).
13. ACP (64-73) Purified Yield: (18.0 mg, 46%); ES-MS Mr 1062.9 (calcd 1062.5).
14. TFA hydrolysis of N-substituted peptides (Urban, J.; Vaisar, T.; Shen, R.; Lee, M. S. Int. J. Pept. Protein Res. 1996, 47, 182-189) or dipeptide cleavage from a similar linker (Raju, B.; Kogan, T. P. Tetrahedron Lett. 1997, 38, 4965-4968) have recently been reported. In the systems we have investigated no hydrolysis or dipeptide cleavage have been detected after a 2 h treatment with TFA:DCM, (40:60).
15. TFA hydrolysis of N-substituted peptides (Urban, J.; Vaisar, T.; Shen, R.; Lee, M. S. Int. J. Pept. Protein Res. 1996, 47, 182-189) or dipeptide cleavage from a similar linker (Raju, B.; Kogan, T. P. Tetrahedron Lett. 1997, 38, 4965-4968) have recently been reported. In the systems we have investigated no hydrolysis or dipeptide cleavage have been detected after a 2 h treatment with TFA:DCM, (40:60).