Molecular transporter between polymer platforms: Highly efficient chemoenzymatic glycopeptide synthesis by the combined use of solid-phase and water-soluble polymer supports

Angewandte Chemie - International Edition

Volumn 44, Issue 17, 2005, Pages 2534-2537

  Fumoto, Masataka ^c,d   Hinou, Hiroshi ^a   Matsushita, Takahiko ^b   Kurogochi, Masaki ^b   Ohta, Takashi ^a   Ito, Takaomi ^d   Yamada, Kuriko ^c,e   Takimoto, Akio ^d   Kondo, Hirosato ^d   Inazu, Toshiyuki ^f   Nishimura, Shin Ichiro ^a,b  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

^c Research Association for Biotechnology   (Japan)

^d SHIONOGI AND CO LTD   (Japan)

^e HITACHI HIGH TECHNOLOGIES CORPORATION   (Japan)

^f TOKAI UNIVERSITY   (Japan)

Author keywords

Enzymes; Glycopeptides; Polymers; Solid phase synthesis; Synthetic methods

Indexed keywords

AMINO ACIDS; SYNTHESIS (CHEMICAL);

CHEMOSELECTIVE BLOTTING; ENZYMATIC SYNTHESIS; GLYCOPEPTIDES; PHOTOSELECTIVE CLEAVAGE;

POLYPEPTIDES;

GLYCOPEPTIDE; POLYMER; WATER;

ARTICLE; CHEMISTRY; SOLUBILITY; SYNTHESIS;

GLYCOPEPTIDES; POLYMERS; SOLUBILITY; WATER;

EID: 18044391505     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200463065     Document Type: Article

References (29)

1. a) R. B. Merrifield, J. Am. Chem. Soc. 1963, 85, 2149;
2. b) R. B. Merrifield, Angew. Chem. 1985, 97, 801; Angew. Chem. Int. Ed. Engl. 1985, 24, 799.
3. b) R. B. Merrifield, Angew. Chem. 1985, 97, 801; Angew. Chem. Int. Ed. Engl. 1985, 24, 799.
4. a) N. D. Sinha, J. Biernat, J. McManus, H. Köster, Nucleic Acids Res. 1984, 12, 4539;
5. b) M. H. Caruthers, Science 1985, 230, 281.
6. a) S. J. Danishefsky, K. F. McClure, J. T. Randolph, R. B. Ruggeri, Science 1993, 260, 1307;
7. b) O. J. Plante, E. R. Palmacci, P. H. Seeberger, Science 2001, 291, 1523.
8. For example: a) K. M. Koeller, C.-H. Wong, Chem. Rev. 2000, 100, 4465; b) M. Meldal, F.-I. Auzanneau, O. Hindsgaul, M. M. Monica, J. Chem. Soc. Chem. Commun. 1994, 1849; c) O. Seitz, C.-H. Wong, J. Am. Chem. Soc. 1997, 119, 8766.
9. For example: a) K. M. Koeller, C.-H. Wong, Chem. Rev. 2000, 100, 4465; b) M. Meldal, F.-I. Auzanneau, O. Hindsgaul, M. M. Monica, J. Chem. Soc. Chem. Commun. 1994, 1849; c) O. Seitz, C.-H. Wong, J. Am. Chem. Soc. 1997, 119, 8766.
10. For example: a) K. M. Koeller, C.-H. Wong, Chem. Rev. 2000, 100, 4465; b) M. Meldal, F.-I. Auzanneau, O. Hindsgaul, M. M. Monica, J. Chem. Soc. Chem. Commun. 1994, 1849; c) O. Seitz, C.-H. Wong, J. Am. Chem. Soc. 1997, 119, 8766.
11. Y. C. Lee, R. T. Lee, Acc. Chem. Res. 1995, 28, 321.
12. For example: a) S.-I. Nishimura, K. Matsuoka, Y. C. Lee, Tetrahedron Lett. 1994, 31, 5657; b) S.-I. Nishimura, K. Yamada, J. Am. Chem. Soc. 1997, 119, 10555; c) K. Yamada, E. Fujita, S.-I. Nishimura, Carbohydr. Res. 1998, 305, 443.
13. For example: a) S.-I. Nishimura, K. Matsuoka, Y. C. Lee, Tetrahedron Lett. 1994, 31, 5657; b) S.-I. Nishimura, K. Yamada, J. Am. Chem. Soc. 1997, 119, 10555; c) K. Yamada, E. Fujita, S.-I. Nishimura, Carbohydr. Res. 1998, 305, 443.
14. For example: a) S.-I. Nishimura, K. Matsuoka, Y. C. Lee, Tetrahedron Lett. 1994, 31, 5657; b) S.-I. Nishimura, K. Yamada, J. Am. Chem. Soc. 1997, 119, 10555; c) K. Yamada, E. Fujita, S.-I. Nishimura, Carbohydr. Res. 1998, 305, 443.
15. a) H. Herzner, T. Reipen, M. Schultz, H. Kunz, Chem. Rev. 2000, 100, 4495;
16. b) P. M. St. Hilaire, M. Meldal, Angew. Chem. 2000, 112, 1210; Angew. Chem. Int. Ed. 2000, 39, 1162.
17. b) P. M. St. Hilaire, M. Meldal, Angew. Chem. 2000, 112, 1210; Angew. Chem. Int. Ed. 2000, 39, 1162.
18. S.-I. Nishimura, K. Niikura, M. Kurogochi, T. Matsushita, M. Fumoto, H. Hinou, R. Kamitani, H. Nakagawa, K. Deguchi, N. Miura, K. Monde, H. Kondo, Angew. Chem. 2005, 117, 93; Angew. Chem. Int. Ed. 2005, 44, 91.
19. S.-I. Nishimura, K. Niikura, M. Kurogochi, T. Matsushita, M. Fumoto, H. Hinou, R. Kamitani, H. Nakagawa, K. Deguchi, N. Miura, K. Monde, H. Kondo, Angew. Chem. 2005, 117, 93; Angew. Chem. Int. Ed. 2005, 44, 91.
20. C. P. Holmes, J. Org. Chem. 1997, 62, 2370.
21. For pioneering work on enzymatic oligosaccharide synthesis using polymers bearing a photolabile linker, see: U. Zehavi, S. Sadeh, M. Herchman, Carbohydr. Res. 1983, 124, 23.
22. G. Arsequell, L. Krippner, R. A. Dwek, S. Y. C. Wong, J. Chem. Soc. Chem. Commun. 1994, 2383.
23. a) M. Kurogochi, T. Matsushita, S.-I. Nishimura, Angew. Chem. 2004, 116, 4163; Angew. Chem. Int. Ed. 2004, 43, 4071;
24. a) M. Kurogochi, T. Matsushita, S.-I. Nishimura, Angew. Chem. 2004, 116, 4163; Angew. Chem. Int. Ed. 2004, 43, 4071;
25. b) M. Kurogochi, S.-I. Nishimura, Anal. Chem. 2004, 76, 6097.
26. Meldal and co-workers also reported the feasibility of a photolabile linker for facile and efficient product characterization by MALDI-TOF MS in solid-phase glycopeptide synthesis: K. M. Halkes, C. H. Gotfredson, M. Grotli, L. P. Miranda, J. O. Duus, M. Meldal, Chem. Eur. J. 2001, 7, 3584.
27. a) S. Nishiguchi, K. Yamada, Y. Fuji, S. Shibatani, A. Toda, S.-I. Nishimura, Chem. Commun. 2001, 1944;
28. b) A. Toda, K. Yamada, S.-I. Nishimura, Adv. Synth. Catal. 2002, 344, 61;
29. c) N. Nagahori, K. Niikura, R. Sadamoto, M. Taniguchi, A. Yamagishi, K. Monde, S.-I. Nishimura, Adv. Synth. Catal. 2003, 345, 729.