Solid phase synthesis of alkylphosphonopeptides

Tetrahedron

Volumn 52, Issue 6, 1996, Pages 2103-2112

  Wijkmans, Jac C H M ^a   Meeuwenoord, Nico J ^a   Bloemhoff, Wim ^a   Van Der Marel, Gijs A ^a   Van Boom, Jacques H ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONOAMINO ACID; PHOSPHOPEPTIDE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; TECHNIQUE;

EID: 0030061838     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01027-0     Document Type: Article

References (25)

1. See for instance (a) Boyer, P.D.; Krebs, E.G. In The Enzymes, Vol. 17, Boyer, P.D.; Krebs, E.G. Eds.; Academic Press: New York, 1986, p. 192-237;
2. (b) Edelman, A.M.; Blumenthal, D.K.; Krebs, E.G. Ann. Rev. Biochem. 1987, 56, 567-613
3. (a) De Bont, D.B.A.; Moree, W.J.; Van Boom, J.H.; Liskamp, R.M.J. J. Org. Chem. 1993, 58, 1309-1317;
4. (b) Kitas, E.; Küng, E.; Bannwarth, W. Int. J. Peptide Protein Res. 1994, 43, 146-153;
5. (c) Tegge, W. ibid. 1994, 43, 448-453;
6. (d) Mora, N.; Lacombe, J.M.; Pavia, A.A. ibid. 1995, 45, 53-63
7. (a) Tong, G.; Perich, J.W.; Johns, R.B. Tetrahedron Lett. 1990, 31, 3759-3762;
8. (b) Garbay-Jaureguiberry, C.; Ficheux, D.; Roques, B.P. Int. J. Peptide Protein Res. 1992, 39, 523-527;
9. (c) Perich, J.W. Int. J. Peptide Protein Res. 1994, 44, 288-294
10. (a) Burke, T.R., Jr.; Smyth, M.S.; Otaka, A.; Roller, P.P. Tetrahedron Lett. 1993, 34, 4125-4128;
11. (b) Otaka, A.; Burke, T.R., Jr.; Smyth, M.S.; Nomizu, M.; Roller, P.P. ibid. 1993, 34, 7039-7042;
12. (c) Gordeev, M.F.; Patel, D.V.; Barker, P.L.; Gordon, E.M. ibid. 1994, 35, 7585-7588;
13. (d) Otaka, A.; Miyoshi, K.; Burke, T.R., Jr.; Roller, P.P.; Kubota, H.; Tamamura, H.; Fujii, N. ibid. 1995, 36, 927-930
14. Wijkmans, J.C.H.M.; Ottenheim, W.; Kuyl-Yeheskiely, E.; Van der Marel, G.A.; Bloemhoff, W.; Van Boom, J.H. Synthesis 1995, 97-100
15. See for instance: (a) Bannwarth, W.; Trzeciak, A. Helv. Chim. Acta 1987, 70, 175-186;
16. (b) De Bont, H.B.A.; Van Boom, J.H.; Liskamp, R.M.J. Tetrahedron Lett. 1990, 31, 2497-2500;
17. (c) Kitas, E.A.; Knorr, R.; Trzeciak, A.; Bannwarth, W. Helv. Chim. Acta 1991, 74, 1314-1328;
18. (d) Perich, J.W. Int. J. Peptide Protein Res. 1992, 40, 134-140
19. Atherton, E.; Sheppard, R.C. Solid Phase Peptide Synthesis, IRL Press: Oxford, England, 1989, p. 154-155
20. Roelen, H.C.P.F.; Van den Elst, H.; Dreef, C.E.; Van der Marel, G.A.; Van Boom, J.H. Tetrahedron Lett. 1992, 33, 2357-2360
21. Bernatowicz, M.S.; Daniels, S.B. Köster, H. Tetrahedron Lett. 1989, 30, 4645-4648
22. 2O, 3/1, v/v): δ 3.03 (br s, 4H, Hδ Arg), 2.75 (br s, 2H, Hε Lys).
23. Von Arx, E.; Faupel, M.; Brugger, M. J. Chromatogr. 1976, 720, 224-228
24. Kaiser, E.; Colescott, R.L.; Bossinger, C.D.; P.I. Cook, P.I. Anal. Biochem. 1970, 34, 595-598
25. De Bont, H.B.A. Thesis, 1993, Leiden University, The Netherlands, p. 69