The chemo-enzymatic synthesis and evaluation of oligosaccharide-branched cyclodextrins

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 18, 1997, Pages 2353-2356

  Matsuda, Keisuke ^a   Inazu, Toshiyuki ^b   Haneda, Katsuji ^b   Mizuno, Mamoru ^b   Yamanoi, Takashi ^b   Hattori, Kenjiro ^a   Yamamoto, Kenji ^c   Kumagai, Hidehiko ^c  

^a TOKYO POLYTECHNIC UNIVERSITY   (Japan)

^b NOGUCHI INSTITUTE   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CONCANAVALIN A; CYCLODEXTRIN DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; DRUG BINDING; ENZYME ACTIVITY; GLYCOSYLATION; IN VITRO STUDY; LECTIN BINDING; MODEL; MUCOR; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0030799239     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00441-1     Document Type: Article

References (16)

1. Szejtli, J. in Cyclodextrin Technology, 1988, Kluwer Academic Publishers.
2. Froming, K. H.;.Szejtli, J. in Cyclodextrin in Pharmacy, 1993, Kluwer Academic Publishers.
3. Uekama, K.; Hirayama, F.; Irie, T. in Modification of Drug Release by Cydodextrin Derivatives, "New Trends in Cydodextrins and Derivatives", Ed. by D. Duchene, Editions de Sante, Paris, 1991, pp. 409-446.
4. Imata, H.; Kubota, K; Hattori, K.; Aoyagi, M.; Jindoh, C. Bio. Med. Chem. Lett., 1997, 7, 109; Polymer J., 1997, 29, 563.
5. Imata, H.; Kubota, K; Hattori, K.; Aoyagi, M.; Jindoh, C. Bio. Med. Chem. Lett., 1997, 7, 109; Polymer J., 1997, 29, 563.
6. Haneda, K.; Inazu, T.; Yamamoto, K.; Kumagai, H.; Nakahara, Y.; Kobata, A. Carbohydr. Res., 1996, 292, 61.
7. Takegawa, K.; Tabuchi, M.; Yamaguchi, S.; Kondo, A.; Kato, I.; Iwahara, K. J. Biol. Chem., 1995, 270, 3094.
8. Wang, L. X.; Fan, J. Q.; Lee, Y. C. Tetrahedron Lett., 1996, 37, 1975.
9. Shuster, S. C.; Swanson, R. V.; Alex, L. A.; Bourret, R. B.; Simon, M. I. Nature, 1993, 365, 343.
10. Inazu, T; Mizuno, M.; Kohda, Y.; Kobayashi, K.; Yaginuma, H. "Peptide Chemistry 1995", Ed. by Nishi, N., Protein Research Foundation, Osaka (1996), pp. 61-64.
11. Kadowaki, S.; Yamamoto, K.; Fujisaki, M.; Izumi, K.; Tochikura, T. Agric. Biol. Chem., 1990, 54, 97.
12. Tai, T.; Yamashita, K.; Ogata-Arakawa, M.; Koide, N.; Muramatsu, T.; Iwashita, S.; Inoue, Y.; Kobata, A. J. Biol. Chem., 1975, 250, 8569.
13. HPLC was carried out using a Mightysil RD-18 column of size φ 6 x 250 mm by linear increase of acetonitrile from 15 to 25 in 0.1 % trifluoroacetic acid over 30 min at a flow rate of 1.2 ml/min with detection of 254 nm due to the Fmoc group. Retention time for 3: 25.8 min (single); for 7: 17.8 min; for 8: 17.6 min.; for 9: 15.5 min. There was no peaks found in the products beside residual 3 at 25.0 min. The yield of transglycosylation with Endo-M in Fig. 1 was obtained from these spectra.
14. Characterization of compound 3: MALDI-TOF MS: found m/z 1699, calcd. 1696, for 7: MALDI-TOF MS: found m/z 2870, calcd. 2871, for 8: MALDI-TOF MS; found m/z 3121, calcd. 3115, for 9: MALDI-TOF MS: found m/z 3695, calcd. 3698.
15. Edwards, P. R.; Gill, A.; Pollard-Knight, D. V.; Hoare, M.; Buckle, P. E.; Lowe, P. A.; Leatherbarrow, R. J.; Anal. Biochem., 1995, 231, 210.
16. Mega, T.; Oku, H; Hase, S. J. Biochem., 1992, 111, 396.