Solid phase synthesis of β-peptides via Arndt-Eister homologation of Fmoc-protected amino acid diazoketeones

Tetrahedron Letters

Volumn 38, Issue 35, 1997, Pages 6145-6148

  Marti, Roger E ^a   Bleicher, Konrad H ^a   Bair, Kenneth W ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CIRCULAR DICHROISM; DRUG SYNTHESIS; MASS SPECTROMETRY; PEPTIDE SYNTHESIS; REACTION ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 0030811504     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01420-2     Document Type: Article

References (26)

1. For a recent example, see: Adams, P.D.; Sellers, W.R.; Sharma, S.K.; Wu, A.D.; Nalin, C.M.; Kaelin, W.G. Mol. Cell. Biol. 1996, 16, 6623-6633.
2. (a) Giannis, A.; Kolter, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267.
3. (b) Gante, J. Angew. Chem. Int. Ed. Engl. 1994, 33, 1699-1720.
4. (a) Bayer, E. Angew. Chem. Int. Ed. Engl. 1991, 30, 113-129.
5. (b) Jung, G.; Beck-Sickinger, A.G. Angew. Chem. Int. Ed. Engl. 1992, 31, 367-383.
6. (a) Seebach, D.; Overhand, M.; Kühnle, F.N.M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913-941.
7. (b) Seebach, D.; Ciceri, P.E.; Overhand, M.; Jaun, B.; Rigo, D.; Oberer, L.; Hommel, U.; Amstutz, R.; Widmer, H. Helv. Chim. Acta 1996, 79, 2043-2066.
8. (c) Seebach, D; Matthews, J.L.; Meden, A.; Wessels, T.; Baerlocher, C.; McCusker, L.B. Helv. Chim. Acta 1997, 80, 173-182.
9. Appella, D.H.; Christianson, L.A.; Karle, I.L.; Powell, D.R.; Gellman, S.H. J. Am. Chem. Soc. 1996, 118, 13071-13072.
10. (a) Podlech, J.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1995, 34, 471-471.
11. (b) Podlech, J.; Seebach, D. Liebigs Ann. 1995, 1217-1228.
12. (c) Guibourdenche, C.; Podlech, J.; Seebach, D. Liebigs Ann. 1996, 1121-1129.
13. For reviews, dealing with the synthesis of β-amino acids, see: (a) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichchim. Acta 1994, 27, 3-11. (b) Cole, D.C. Tetrahedron 1994, 50, 9517-9582.
14. For reviews, dealing with the synthesis of β-amino acids, see: (a) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichchim. Acta 1994, 27, 3-11. (b) Cole, D.C. Tetrahedron 1994, 50, 9517-9582.
15. Guibourdenche, C.; Seebach, D.; Natt, F. Helv. Chim. Acta 1997, 80, 1-13.
16. ™ Fmoc/OtBu protocol (HBTU/HOBt activation) on Fmoc-Ile-Wang resin or H-Pro-2-chlorotrityl resin.
17. 2 in ether (CAUTION) starting from the Fmoc-protected α-amino acids. In all cases the crude diazoketones are obtained as yellow solids, which were used without further purification.
18. (a) Kaiser, E.; Colescott, R.L.; Bossinger, C.D.; Cook, P.I Anal. Biochem. 1970, 34, 595-599.
19. (b) Sarin, V.; Kent, S.; Tam, J.; Merrifield, B. Anal. Biochem. 1981, 117, 147-157.
20. RP-HPLC was performed on a Deltapak C18 column (5 μ, 100 Å) with a gradient 10-100% acetonitrile in water (0.1% TFA) over 15 min with a diode array detector.
21. Wang, S.-S. J. Am. Chem. Soc. 1973, 95, 1328-1333.
22. Rink, H. Tetrahedron Lett. 1987, 28, 3787-3790.
23. 2 and dried in vacuo.
24. For recent reviews about combinatorial chemistry, see: (a) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337. (b) Thompson, L.A.; Ellman, J.A. Chem. Rev. 1996, 96, 555- 600. (c) Hermkens, P.H.H; Ottenheijm, H.C.J.; Rees, D.C. Tetrahedron 1997, 53, 5643-5678.
25. For recent reviews about combinatorial chemistry, see: (a) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337. (b) Thompson, L.A.; Ellman, J.A. Chem. Rev. 1996, 96, 555-600. (c) Hermkens, P.H.H; Ottenheijm, H.C.J.; Rees, D.C. Tetrahedron 1997, 53, 5643-5678.
26. For recent reviews about combinatorial chemistry, see: (a) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337. (b) Thompson, L.A.; Ellman, J.A. Chem. Rev. 1996, 96, 555- 600. (c) Hermkens, P.H.H; Ottenheijm, H.C.J.; Rees, D.C. Tetrahedron 1997, 53, 5643-5678.