Solid-phase synthesis of peptide aminoalkylamides using an allyl linker

Tetrahedron Letters

Volumn 37, Issue 17, 1996, Pages 3031-3034

  Kaljuste, Kalle ^a   Undén, Anders ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PEPTIDE SYNTHESIS; TECHNIQUE;

EID: 0029897843     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00461-3     Document Type: Article

References (19)

1. Abbreviations used in this paper: Boc, tert-butoxycarbonyl; BOP, benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphoniumhexafluorophosphate, DCC, dicyclohexylcarbodiimide; DCHA, dicyclohexylamine; DIEA, diisopropylethylamine; DMAP, 4,4-dimethylaminopyridine, DMF, N,N-dimethylformamide; Fmoc, 9-Fluorenylmethoxycarbonyl; HOBt, 1-hydroxybenzotriazole; tBu, tert-butyl; Trt, triphenylmethyl.
2. a) Gordon, E. M. Curr. Opin. Biotech.. 1995, 6, 624-631.
3. b) Früchtel, J. S.; Jung, G. Ang. Chem. Int. Ed. Engl. 1996, 35, 17-42.
4. a) Breipohl, G.; Knolle, J.; Geiger, R. Tetrahedron Lett. 1987, 28, 5647-5650.
5. b)van Vliet, A.; Smulders, R. H. P H; Rietman, B. H.; Tesser, G. I. Protected Peptide Intermediates Using Trityl Linker on Solid Support. In Innovations and Perspectives in Solid Phase Synthesis: Peptides, Polypeptides and Oligonucleotides; Epton, R. (Ed.) Intercept Ltd.: Andover. 1992; pp. 475-477.
6. a) Kunz, H.; Dombo, B. Ang. Chem. Int. Ed. Engl. 1988, 27, 711-713.
7. b) Blankemeyer-Menge, B.; Frank, R. Tetrahedron Lett. 1988, 29, 5871-5874.
8. Lloyd-Williams, P; Jou, G., Albericio, F.; Giralt, E. Tetrahedron Lett. 1991, 32, 4207-4210.
9. Lloyd-Williams, P; Albericio, F.; Giralt, E. Tetrahedron, 1993, 49, 11065-11133.
10. Lloyd-Williams, P; Merzouk, A.; Guibé, F. G.; Albericio, F.; Giralt, E. Tetrahedron Lett. 1994, 35, 4437-4440.
11. Grishin, E., V.; Volkova, T., M.; and Arseniev, A., S. Toxicon, 1989, 27, 541-549.
12. Guibé, F. G.; Dangles, D.; Balavoine, G.; and Loffet, A. Tetrahedron Lett. 1989, 30, 2641-2644. The linker is commercially available from Propeptide, France.
13. 2. The substitution level obtained was 61%. It was determined by collecting the washing solvents after the coupling of N-Trt-1,5-diaminopentane, diluting the sample in DMF containing 3% DIEA and determining the concentration of 4-nitrophenol spectrophotometrically at 435 nm.
14. 2.
15. 2), 172.9; CO(NH), 175.8. Di-aminopentane moiety (numbered from NH end): δ C-1, 40.0; C-2, 26.9; C-3, 23.3, C-4, 28.3; C-5, 39.6.
16. Approximately 1 mg of resin was mixed with 100 μ1 of propionic acid/HCl mixture (50/50 v/v) and samples were heated 20 h at 105°C. Amino acid analysis was performed by Fmoc method as described in: Handbook of Amino Acid Analysis. Theory & Laboratory Techniques, Pharmacia LKB Biotechnology AB, 1988. The overall substitution level and cleavage yield was determined by comparing the relative ratio of Asp/Ala before and after the cleavage. The overall substitution level obtained was 52%.
17. Bodansky, M.; Kwei, J. Z. Int. J. Peptide Protein Res. 1978, 12, 69-74.
18. Ressler, C.; Ratzkin, H. J. Org. Chem. 1961, 26, 3356-3360.
19. 2 and Val-Gly-Phe-(1,5-diaminopentane) in cleavage products analysed by HPLC at 215 nm.