Detection and control of aspartimide formation in the synthesis of cyclic peptides

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 4, 2005, Pages 1065-1068

  Flora, David ^a   Mo, Huaping ^a   Mayer, John P ^a   Khan, M Amin ^a   Yan, Liang Z ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

Allyl ester; Aspartimide; Cyclic peptides; NMR

Indexed keywords

ALLYL COMPOUND; ASPARTIC ACID; CYCLOPEPTIDE; ESTER DERIVATIVE; IMIDE; LACTAM; MACROCYCLIC COMPOUND;

ARTICLE; DRUG DETERMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE;

EID: 16244421381     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.12.025     Document Type: Article

References (22)

1. J.N. Lambert, J.P. Mitchell, and K.D. Roberts J. Chem. Soc., Perkin Trans. 1 2001 471 484
2. P. Li, P.P. Roller, and J. Xu Curr. Org. Chem. 6 2002 411 440
3. R.T. Dorr, R. Lines, N. Levine, C. Brooks, L. Xiang, V.J. Hruby, and M.E. Hadley Life Sci. 58 1996 1777 1784
4. H. Wessells, V.J. Hruby, J. Hackett, G. Han, P. Balse-Srinivasan, and T.W. Vanderah Ann. NY Acad. Sci. 994 2003 90 95
5. B.S. Hamilton, and H.N. Doods Obes. Res. 10 2002 182 187
6. H. Wessells, K. Fuciarelli, J. Hansen, M.E. Hadley, V.J. Hruby, R. Dorr, and N. Levine J. Urol. (Baltimore) 160 1998 389 393
7. F. Al-Obeidi, A.M. de L. Castrucci, M.E. Hadley, and V.J. Hruby J. Med. Chem. 32 1989 2555 2561
8. F. Al-Obeidi, M.E. Hadley, B.M. Pettitt, and V.J. Hruby J. Am. Chem. Soc. 111 1989 3413 3416
9. P. Grieco, P. Balse-Srinivasan, G. Han, D. Weinberg, T. MacNeil, L.H.T. Van der Ploeg, and V.J. Hruby J. Pept. Res. 62 2003 199 206
10. P. Grieco, P.M. Gitu, and V.J. Hruby J. Pept. Res. 57 2001 250 256
11. Vigil-Cruz, C. Sandra, and J.V. Aldrich Lett. Pept. Sci. 6 1999 71 75
12. M. Mergler, F. Dick, B. Sax, P. Weiler, and T. Vorherr J. Pept. Sci. 9 2003 36 46
13. M. Mergler, F. Dick, B. Sax, C. Stähelin, and T. Vorherr J. Pept. Sci. 9 2003 518 526
14. J.L. Lauer, C.G. Fields, and G.B. Fields Lett. Pept. Sci. 1 1994 197 205
15. N. Thieriet, J. Alsina, E. Giralt, F. Guibé, and F. Albericio Tetrahedron Lett. 38 1997 7275 7278
16. 2O/anisole (92/4/2/2%, v/v) for 2 h at room temperature
17. E.C. Roos, P. Bernabe, H. Hiemstra, W.N. Speckamp, B. Kaptein, and W.H.J. Boesten J. Org. Chem. 60 1995 1733 1740
18. E.C. Roos, P. Bernabe, H. Hiemstra, W.N. Speckamp, B. Kaptein, and W.H.J. Boesten Tetrahedron Lett. 32 1991 6633 6636
19. Detailed method of NMR experiment, spectra, and assignment strategies are available as Supplemental data
20. HPLC conditions: solvent A: water with 0.1%TFA; solvent B: acetonitrile with 0.1%TFA; column: Phenomenex, Jupiter C18 reverse-phase, 4.6 x 250 mm, 5 μM, 300 Å pore size; gradient: linear from 10% B to 40% B over 20 min, then 90% B for 5 min, and 0% B for another 5 min. Wavelength used for detection: 214 nm
21. S.-S. Wang J. Am. Chem. Soc. 95 1973 1328 1333
22. J. Meienhofer, M. Waki, E.P. Heimer, T.J. Lambros, R.C. Makofske, and C.D. Chang Int. J. Pept. Protein Res. 13 1979 35 42