L-α-Methylhomoisoserine: A New Versatile Building Block for Peptide and Depsipeptide Modification

Synlett

Volumn , Issue 12, 2003, Pages 1826-1829

  Radics, Gábor ^a   Koksch, Beate ^a   El Kousy, Salah M ^b   Spengler, Jan ^a   Burger, Klaus ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b Menoufia University   (Egypt)

Author keywords

Amino acid hydroxamates; Arndt Eistert synthesis; Citramalic acid; Curtius rearrangement; Hexafluoroacetone; Wolff rearrangement; amino hydroxy methylbutyric acid

Indexed keywords

4 AMINOBUTYRIC ACID; ALPHA METHYLHOMOISOSERINE; DEPSIPEPTIDE; MALIC ACID DERIVATIVE; SERINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; PROTEIN MODIFICATION;

EID: 0142123041     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41477     Document Type: Article

References (45)

1. Hexafluoroacetone as protecting and activating reagent in α-hydroxy acid chemistry, Part 4. (a) For Part 3, see: Radics, G.; Pires, R.; Koksch, B.; El-Kousy, S. M.; Burger, K. Tetrahedron Lett. 2003, 44, 1059. (b) Part 2: Burger, K.; Böttcher, C.; Radics, G.; Hennig, L. Tetrahedron Lett. 2001, 42, 3061.
2. Hexafluoroacetone as protecting and activating reagent in α- hydroxy acid chemistry, Part 4. (a) For Part 3, see: Radics, G.; Pires, R.; Koksch, B.; El-Kousy, S. M.; Burger, K. Tetrahedron Lett. 2003, 44, 1059. (b) Part 2: Burger, K.; Böttcher, C.; Radics, G.; Hennig, L. Tetrahedron Lett. 2001, 42, 3061.
3. Soth, M. J.; Nowick, J. S. J. Org. Chem. 1999, 64, 276; and references cited therein.
4. (a) Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015.
5. (b) Seebach, D.; Matthews, J. L.; Meden, A.; Wessel, T.; Baerlocher, C.; McCusker, L. B. Helv. Chim. Acta 1997, 80, 173.
6. (c) Krauthäuser, S.; Christianson, L. A.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1997, 119, 11719.
7. (d) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173.
8. (e) Banerjee, A.; Balaram, P. Curr. Sci. 1997, 73, 1067.
9. (f) Brenner, M.; Seebach, D. Helv. Chim. Acta 2001, 84, 1181.
10. (g) Seebach, D.; Sifferlen, T.; Bierbaum, D. J.; Rueping, M.; Jaun, B.; Schweizer, B.; Schaefer, J.; Mehta, A. K.; O'Connor, R. D.; Meyer, B. H.; Ernst, M.; Glättli, ?. Helv. Chim. Acta 2002, 85, 2877.
11. (h) Gademann, K.; Häne, A.; Rueping, M.; Jaun, B.; Seebach, D. Angew. Chem., Int. Ed. 2003, 42, 1534.
12. (a) Woll, M. G.; Lai, J. R.; Guzei, I. A.; Taylor, S. J. C.; Smith, M. E. B.; Gellman, S. H. J. Am. Chem. Soc. 2001, 123, 11077.
13. (b) Karle, I. L.; Pramanik, A.; Banerjee, A.; Bhattacharjya, S.; Balaram, P. J. Am. Chem. Soc. 1997, 119, 9087.
14. (a) Maji, S. K.; Banerjee, R.; Velmurugan, D.; Razak, A.; Fun, H. K.; Banerjee, A. J. Org. Chem. 2002, 67, 633; and references cited therein.
15. (b) Hintermann, T.; Gademann, K.; Jaun, B.; Seebach, D. Helv. Chim. Acta 1998, 81, 983.
16. Frackenpohl, J.; Arvidsson, P. I.; Schreiber, J. V.; Seebach, D. ChemBioChem. 2001, 2, 445.
17. Hanessian, S.; Luo, X.; Schaum, R.; Michnick, S. J. Am. Chem. Soc. 1998, 720, 8569.
18. (a) Kondo, S.; Tamura, A.; Gomi, S.; Ikeda, Y.; Takeuchi, T.; Mitsuhashi, S. J. Antibiot. 1993, 46, 310.
19. (b) Kawaguchi, H.; Naito, T. In Chronicles of Drug Discovery, 2; Bindra, J. S.; Lednicer, D., Eds.; J. Wiley & Sons: New York NY, 1983, 207.
20. (c) Kawasaki, H.; Naito, T. J. Antibiot. 1972, 25, 895.
21. (d) Woo, W. P. K.; Dion, H.; Bartz, Q. R. Tetrahedron Lett. 1971, 36, 2617.
22. Shioiri, T.; Hamada, Y.; Matsuura, F. Tetrahedron 1995, 51, 3939.
23. Harris, K.; Sih, C. J. Biocatalysis 1992, 5, 195.
24. (a) Iriuchijima, S.; Ogawa, M. Synthesis 1982, 41.
25. (b) Brehm, L.; Krogsgaard-Larsen, P. Acta Chem. Scand. 1979, B33, 52.
26. (c) Yoneta, Y.; Shibahara, S.; Fukatsu, S.; Seki, S. Bull. Chem. Soc. Jpn. 1978, 51, 3296.
27. (d) Horiuchi, Y.; Akita, E.; Ito, T. Agric. Biol. Chem. 1976, 40, 1649.
28. (e) Yamada, Y.; Okada, H. Agric. Biol. Chem. 1976, 40, 1437.
29. (a) Weygand, F.; Burger, K. Chem. Ber. 1966, 99, 2880.
30. (b) Pires, R.; Burger, K. Synthesis 1996, 281.
31. Burger, K.; Windeisen, E.; Heistracher, E.; Lange, T.; Abdel Aleem, H. A. A. Monatsh. Chem. 2002, 133, 41.
32. (a) Doyle, M. P.; Mc Kervey, M. A. Chem. Commun. 1997, 983.
33. (b) Meier, H.; Zeller, K.-P. Angew. Chem., Int. Ed. Engl. 1974, 14, 32.
34. (c) Guibourdenche, C.; Seebach, D.; Natt, F. Helv. Chim. Acta 1997, 80, 1.
35. (d) Leggio, A.; Ligouri, A.; Procopio, A.; Sindona, G. J. Chem. Soc., Perkin Trans. 1 1997, 1969.
36. Sheradsky, T. In The Chemistry of the Azido Group; Patai, S., Ed.; Interscience Publishers, Wiley & Sons: Chichester, 1971, 341.
37. Vasanthakumar, G.-R.; Suresh Babu, V. V. Tetrahedron Lett. 2003, 44, 4099; and references cited therein.
38. (a) Murahashi, D.; Oda, T.; Sugahara, S.; Masui, Y. J. Org. Chem. 1990, 50, 1744.
39. (b) Burke, T. R.; Fesen, M. R.; Mazumder, A.; Wang, J.; Carothers, A. M. ; Grunberger, D.; Drisscoll, J.; Kohn, K.; Pommier, Y. Med. Chem. 1995, 38, 4171.
40. (a) Bourdel, E.; Doulut, S.; Jerretou, G.; Labbe-Jullie, C.; Fehrentz, J.-A.; Doumbia, D.; Kitabgi, P.; Martinez, J. Int. J. Peptide Protein Res. 1996, 48, 148.
41. (b) Pirrung, M. C.; Cao, J.; Chen, J. J. Org. Chem. 1995, 60, 5790.
42. Johnson, J. E.; Springfield, J. R.; Hwang, J. S.; Haynes, L. J.; Cunningham, W. C.; Mc Claugherty, D. L. Tetrahedron Lett. 1971, 36, 284.
43. Burger, K.; Schedel, H.; Spengler, J. Amino Acids 1999, 16, 287.
44. Pumpor, K.; Windeisen, E.; Burger, K. Heterocycl. Chem. 2003, 40, 329.
45. Böttcher, C.; Burger, K. Tetrahedron Lett. 2003, 44, 4223.