Synthesis of the tetrasaccharide Glc α (1→3) Man α (1→2) Man α (1→2) Man α (OMe) as inhibitor of calnexin binding to GlcMan9GlcNAc2

Journal of Carbohydrate Chemistry

Volumn 21, Issue 1-2, 2002, Pages 123-130

  Cherif, Slim ^a   Clavel, Jean Marc ^a   Monneret, Claude ^a  

^a INSTITUT CURIE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CALNEXIN; CARBOHYDRATE DERIVATIVE; ETHYL O (2,3,4,6 TETRA O BENZYL ALPHA DEXTRO GLUCOPYRANOSYL) (1-3) 2 O BENZYL 4,6 O BENZYLIDENE 1 THIO ALPHA DEXTRO MANNOPYRANOSIDE; GLYCOSIDE; METHYL O (3 O BENZYL 4,6 O BENZYLIDENE ALPHA DEXTRO MANNOPYRANOSYL) (1-2) 3 O BENZYL 4,6 O BENZYLIDENE ALPHA DEXTRO MANNOPYRANOSIDE; METHYL O (ALPHA DEXTRO GLUCOPYRANOSYL) (1-3) O (ALPHA DEXTRO MANNOPRYANOSYL) (1-2) O (ALPHA DEXTRO MANNOPYRANOSYL) (1-2) ALPHA DEXTRO MANNOPYRANOSE; PYRANOSIDE; TRICHLOROACETIMIDIC ACID; UNCLASSIFIED DRUG;

ARTICLE; DEACETYLATION; DRUG EFFECT; DRUG SYNTHESIS; IC 50; POLYMERIZATION; PROTEIN BINDING; STEREOCHEMISTRY;

EID: 0035998801     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-120003743     Document Type: Article

References (14)

1. Welsh, M.J.; Smith, A.E. Molecular mechanisms of CFTR chloride channel dysfunction in cystic fibrosis. Cell 1993, 73, 1251-1254.
2. Kopito, R.R. Biosynthesis and degradation of CFTR. Physiol. Rev. 1999, 79, S167-S173.
3. Riordan, J.R. Cystic fibrosis as a disease of misprocessing of the cystic fibrosis transmembrane conductance regulator glycoprotein. Am. J. Hum. Genet. 1999, 64, 1499-1504.
4. Helenius, A. How N-linked oligosaccharide affect glycoprotein folding in the endoplasmic reticulum. Mol. Biol. Cell 1994, 5, 253-265.
5. Denning, G.M.; Anderson, M.P.; Amara, J.F.; Marshall, J.; Smith, A.E.; Welsh, M.J. Processing of mutant cystic fibrosis transmembrane conductance regulator is temperature-sensitive. Nature 1992, 358, 761-764.
6. Li, C.; Ramjeesingh, M.; Reyes, E.; Jensen, T.; Chang, X.; Rommens, J.M.; Bear, C.E. The cystic fibrosis mutation (ΔF508) does not influence the chloride channel activity of CFTR. Nat. Genet. 1993, 3, 312-316.
7. 2 oligosaccharide as an initial step in recognizing unfolded glycoproteins. J. Biol. Chem. 1995, 270, 4697-4704.
8. Spiro, R.G.; Zhu, Q.; Bhoyroo, V.; Söling, H.-D. Definition of the lectin-like properties of the molecular chaperone, calreticulin and demonstration of its copurification with endomannosidase from rat liver golgi. J. Biol. Chem. 1996, 271, 11588-11594.
9. Cherif, S.; Clavel, J.-M.; Monneret, C. A synthetic approach to the glycan chain of high mannose type N-glycoprotein. J. Carbohydr. Chem. 1998, 17, 1203-1218.
10. Vassilakos, A.; Michalak, M.; Lehrman, M.A.; Williams, D.B. Oligosaccharide binding characteristics of the molecular chaperones calnexin and calreticulin. Biochemistry 1998, 37, 3480-3490.
11. Jain, R.K.; Liu, X.-G.; Oruganti, S.R.; Chandrasekaran, E.V.; Matta, K.L. Synthesis of oligosaccharide substrates for N-linked glycoprotein processing enzymes. Carbohydr. Res. 1995, 271, 185-196.
12. Garegg, P.J.; Kvarnström, I.; Niklasson, A.; Niklasson, G.; Svensson, S.C.T. Partial substitution of thioglycosides by phase transfer catalyzed benzoylation and benzylation. J. Carbohydr. Chem. 1993, 12, 933-953.
13. Oshitari, T.; Kobayashi, S. Preparation of 2-O-(3-O-Carbamoyl-α-D-mannopyranosyl)-L-gulopyranose: synthetic study on the sugar moiety of antitumor antibiotic bleomycin. Tetrahedron Lett. 1995, 36, 1089-1092.
14. Fügedi, P.; Garegg, P.J. A novel promoter for the efficient construction of 1,2-trans linkages in glycoside synthesis, using thioglycosides as glycosyl donors. Carbohydr. Res. 1986, 149, C9-C12.