On the use of PyAOP, a phosphonium salt derived from HOAt, in solid-phase peptide synthesis

Tetrahedron Letters

Volumn 38, Issue 27, 1997, Pages 4853-4856

  Albericio, Fernando ^a   Cases, Marta ^a   Alsina, Jordi ^a   Triolo, Salvatore A ^b   Carpino, Louis A ^c   Kates, Steven A ^b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b PERKINELMER INC   (United States)

^c UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CYCLOPEPTIDE; PEPTIDE; PHOSPHONIUM DERIVATIVE;

ARTICLE; CYCLIZATION; DECOMPOSITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PEPTIDE SYNTHESIS; REACTION ANALYSIS;

EID: 0030975051     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01011-3     Document Type: Article

References (28)

1. Abbreviations used in this article: ACP, acyl carrier protein; Al, allyl; Aib, aminoisobutyric acid; BOP, benzotriazol-1-yloxy-tris-(dimethylamino)phosphonium hexafluorophosphate; CsA, cyclosporine; DIEA, N,N-diisopropylethylamine; DIPCDI, N,N′-diisopropylcarbodiimide; DMAP, N,N-dimethylaminopyridine; DMF, N,N-dimethylformamide; FAB-MS, Fast atom bombardment mass spectrometry; Fmoc, 9-fluorenylmethoxycarbonyl; HAPyU, 1-(1-pyrrolidinyl-1H,2,3-triazolo[4,5-b]pyridin-1-ylmethylene) pyrrolidinium hexafluorophosphate N-oxide; HATU, N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N- methylmethan-aminium hexafluorophosphate N-oxide; HBTU, N-[(1H-benzotriazol-1-yl)(dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphate N-oxide, HMPB, 4-(4-hydroxymethyl-3-methoxyphenoxy)-butyric acid; HPLC, high performance liquid chromatography; HOAc, acetic acid; HOAt, 1-hydroxy-7-azabenzotriazole; HOBt, 1-hydroxybenzotriazole; NMM, N-methylmorpholine; PAL, 5-(4-aminomethyl-3,5-dimethoxyphenoxy)valeric acid; PAC, 3-(4-hydroxymethylphenoxy) propionic acid; PEG-PS, polyethylene glycol-polystyrene graft; PyAOP, 7-azabenzotriazol-1-yl-oxytris(pyrrolidino)phosphonium hexafluorophosphate; PyBOP, benzotriazol-1-yloxytris(pyrrolidino)phosphonium hexafluorophosphate; Reagent R, TFA-1,2-ethanedithiol-p-cresol-anisole (90:5:3:2); TFA, trifluoroacetic acid; Trt, triphenylmethyl (trityl). Amino acid denotes L-configuration unless otherwise noted.
2. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397-4398.
3. (a) Carpino, L. A.; El-Faham, A.; Minor, C. A.; Albericio, F. J. Chem. Soc., Chem. Commun. 1994, 201-203;
4. (b) Carpino, L.; El-Faham, A.; Albericio, F. Tetrahedron Lett. 1994, 35, 2279-2282;
5. (c) Ehrlich, A.; Rothemund, S.; Brudel, M.; Beyermann, M.; Carpino, L.A.; Bienert, M. Tetrahedron Lett. 1993, 34, 4781-4784.
6. Castro, B.; Dormoy, J.R.; Evin G.; Selve, C. Tetrahedron Lett. 1975, 1219-1222.
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8. Pyrrolidine-derived phosphonium salts (PyXOP) are advantageous relative to the corresponding dimethylamino derivatives because the phosphoramide side-product is less toxic. Furthermore, pyrrolidino derivatives of both phosphonium and uronium salts are slightly more reactive than the dimethylamino derivatives (Kates, S.A.; Carpino, L.A.; Albericio, F., manuscript in preparation).
9. (a) Hancock, W. S.; Prescott, D. J.; Vagelos, P. R.; Marshall, G. R. J. Org. Chem. 1973, 38, 774-781;
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11. Zalipsky, S.; Chang, J. L.; Albericio, F.; Barany, G. Reactive Polymers 1994, 22, 243-258.
12. Albericio, F.; Kneib-Cordonier, N.; Biancalana, S.; Gera, L.; Masada, R. I.; Hudson, D.; Barany, G. J. Org. Chem. 1990, 55, 3730-3743.
13. (a) Mojsov, S.; Mitchell, A.R.; Merrifield, R.B. J. Org. Chem. 1980, 45, 555-560;
14. (b) Gausepohl, H.; Kraft M.; Frank, R.W. Int. J. Pept. Protein Res. 1989, 34, 287-294.
15. (a) Belton, P.; Cotton, R.; Giles, M.B.; Atherton, E.; Horton, J.; Richards, J.D. In Peptides 1988, Jung, G.; Bayer, E. Eds. Walter der Gruyter, Berlin, 1998, pp. 619-621;
16. (b) Auvin-Guette, C.; Frérot, E.; Coste, J.; Rebuffat, S.; Jouin, P.; Bodo, B. Tetrahedron Lett. 1993, 34, 2481-2482.
17. For a review, see Kates, S.A.; Solé, N.A.; Albericio, F.; Barany, G. In Peptides: Design, Synthesis, and Biological Activity; Basava, C.; Anantharamaiah, G.M., Ed.; Birkhäuser: Boston, 1994; pp. 39-58.
18. (a) Gausepohl, H.; Pieles, U.; Frank, R.W. In Proceedings of the 12th American Peptide Symposium, Smith J.A.; Rivier, J.E., ESCOM, Leiden, 1992, pp. 523-524;
19. (b) Story, S.C.; Aldrich, J.V. Int. J. Pept. Protein Res. 1994, 43, 292-296;
20. (c) Arttamangkul, S.; Arbogast, B.; Barofsky, D.; Aldrich, J.V. Lett. Pept. Sci. 1996, 3, 357-370.
21. HCl,H-Phe-OFm (1 equiv) was dissolved in DMF and either the phosphonium or uronium salt (1 equiv) and DIEA (2 equiv) added. After several minutes, HPLC analysis indicated that the phosphonium and uronium salts had disappeared and in the case of the uronium salt a new peak appeared corresponding to the guanidino derivative. If Fmoc-Phe-OH (1 equiv) and DIEA (1 equiv) are added to the phosphonium salt, Fmoc-Phe-Phe-OFm was formed in a few minutes showing that no blocking at the amino terminus occurred.
22. Angell, Y.M.; García-Echeverría, C.; Rich, D.H. Tetrahedron Lett. 1994, 35, 5981-5984.
23. During the course of this work, Rich and co-workers published the synthesis of the same peptide via DIPCDI-HOAt mediated coupling using a different strategy; see Angell, Y.M.; Thomas, T.L.; Flentke, G.R. Rich, D.H. J. Am. Chem. Soc. 1995, 117, 7279-7280.
24. Flörsheimer, A.; Riniker, B. In Peptides 1990; Giralt, E.; Andreu, D. Eds.; ESCOM, Leiden, 1991, pp-131-133.
25. 1-cyclosporine linear peptide with neat TFA led to decomposition of the peptide as shown by HPLC analysis.
26. (a) Gisin, B. F.; Merrifield, R. B. J. Am. Chem. Soc. 1972, 94, 3102-3106;
27. (b) Khosla, M. C.; Smeby, R. R.; Bumpus, F. J. Am. Chem. Soc. 1972, 94, 4721-4724;
28. (c) Alsina, J.; Giralt, E.; Albericio, F. Tetrahedron Lett. 1997, 38, 4195-4198, and references cited therein.