Synthesis of artifical glycoconjugate polymers carrying biologically active trisaccharides with α-D-galactopyranosyl (1→3)and (1→4)-linkage

Tetrahedron Letters

Volumn 39, Issue 47, 1998, Pages 8681-8684

  Nishida, Yoshihiro ^a   Dohi, Hirofumi ^a   Uzawa, Hirotaka ^b   Kobayashi, Kazukiyo ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b NATL INST OF MAT AND CHEM RES   (Japan)

Author keywords

Biologically active compounds; Glycosidation; Polymers; Regiospecificity

Indexed keywords

6 NITROPHENYL BETA LACTOSIDE; ALPHA DEXTRO GALACTOPYRANOSYL (1-3) BETA DEXTRO GALACTOPYRANOSYL (1-4) DEXTRO GLUCOPYRANOSE; ALPHA DEXTRO GALACTOPYRANOSYL (1-4) BETA DEXTRO GALACTOPYRANOSYL (1-4) DEXTRO GLUCOPYRANOSE; GLOBOTRIAOSYLCERAMIDE; GLYCOCONJUGATE; TRISACCHARIDE; UNCLASSIFIED DRUG; VEROTOXIN;

ARTICLE; BINDING AFFINITY; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032547987     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01897-8     Document Type: Article

References (13)

1. [1] Tsuchida A, Akimoto S, Usui T, Kobayashi K. J. Biochem. 1998;123:715.
2. [2] Lee YC, Lee RC, Rice K, Ichikawa Y, Wong T.-C. Pure Appl. Chem. 1991:63:499.
3. [3] Kobayashi K, Akaike T, Usui T. Neoglycoconjugates: Preparation and Applications, Lee YC, Lee RT, Eds: Academic Press, 1994:262-284.
4. [4] Arab S, Lingwood CA. Glycoconjugate J. 1996;13:159.
5. [5] Cooper DKC, Koren E, Oriol R. Immunological Rev. 1994;141:31.
6. [6] Teneberg S, Lonnroth I, Torres Lopez JF, Galili U, Halvarsson MO, Angstrom J, Karlsson KA. Glycobiology 1996;6:599.
7. [7] For recent synthesis of Gb3 ceramide, see Hashimoto S, Sakamoto H, Honda T, Abe H, Nakamura S, Ikegami S. Tetrahedron Lett. 1997;52:8969.
8. [8] For the synthesis of Galα 1,3-linked sugars, see Vic C, Tran CH, Scigelova M, Crout DHG. Chem. Commun. 1997;169 and the related references therein.
9. [9] Page D, Roy R. Glycoconjugate J. 1997;14:345.
10. [10] Nishida Y, Thiem J. Carbohydr. Res. 1994:263:295.
11. [11] Otera J, Nozaki H. Tetrahedron Lett. 1986;27:5743.
12. [12] To increase the α-selectivity in the galactosylation, 6-0-acetylated donor 4 was employed. The donor 4 was prepared from methyl per-0-benzylated D-galactopyranoside through regioselective acetolysis of 1-OMe and 6-OBn groups followed by selective deacetylation of the anomeric O-Ac.
13. [13] Roy R, Tropper FD, Romanoeska A. Bioconjugate Chem. 1992;3:256.