Synthesis, protein-binding ability and phytoalexin-elicitor activity of epoxyalkyl (1→3)-β-D-oligoglucosides

Glycoconjugate Journal

Volumn 20, Issue 7-8, 2003, Pages 427-433

  Huang, Gang Liang ^a   Liu, Man Xi ^a   Mei, Xin Ya ^b   Cao, Yuan Cheng ^a  

^a HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

(1 3) D oligoglucosides; Phytoalexin elicitor activity; Protein binding ability; Synthesis

Indexed keywords

2 PROPENYL 2,3,4,6 TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL (1-3) BIS[2,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYL (1-3)] 2,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSIDE; 2 PROPENYL 2,3,4,6 TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL (1-3) TETRAKIS[2,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYL (1-3)] 2,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSIDE; 2 PROPENYL 2,3,4,6 TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL (1-3) TRIS[2,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYL (1-3)] 2,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSIDE; 2,3 EPOXYPROPYL BETA DEXTRO GLUCOPYRANOSYL (1-3) BIS[BETA DEXTRO GLUCOPYRANOSYL (1-3)] BETA DEXTRO GLUCOPYRANOSIDE; 2,3 EPOXYPROPYL BETA DEXTRO GLUCOPYRANOSYL (1-3) TETRAKIS[BETA DEXTRO GLUCOPYRANOSYL (1-3)] BETA DEXTRO GLUCOPYRANOSIDE; 2,3 EPOXYPROPYL BETA DEXTRO GLUCOPYRANOSYL (1-3) TRIS[BETA DEXTRO GLUCOPYRANOSYL (1-3)] BETA DEXTRO GLUCOPYRANOSIDE; 3 BUTENYL 2,3,4,6 TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL (1-3) BIS[2,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYL (1-3)] 2,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSIDE; 3 BUTENYL 2,3,4,6 TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL (1-3) TETRAKIS[2,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYL (1-3)] 2,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSIDE; 3 BUTENYL 2,3,4,6 TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL (1-3) TRIS[2,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYL (1-3)] 2,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSIDE; 3,4 EPOXYBUTYL BETA DEXTRO GLUCOPYRANOSYL (1-3) BIS[BETA DEXTRO GLUCOPYRANOSYL (1-3)] BETA DEXTRO GLUCOPYRANOSIDE; 3,4 EPOXYBUTYL BETA DEXTRO GLUCOPYRANOSYL (1-3) TETRAKIS[BETA DEXTRO GLUCOPYRANOSYL (1-3)] BETA DEXTRO GLUCOPYRANOSIDE; 3,4 EPOXYBUTYL BETA DEXTRO GLUCOPYRANOSYL (1-3) TRIS[BETA DEXTRO GLUCOPYRANOSYL (1-3)] BETA DEXTRO GLUCOPYRANOSIDE; 4 PENTENYL 2,3,4,6 TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL (1-3) BIS[2,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYL (1-3)] 2,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSIDE; 4 PENTENYL 2,3,4,6 TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL (1-3) TETRAKIS[2,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYL (1-3)] 2,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSIDE; 4 PENTENYL 2,3,4,6 TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL (1-3) TRIS[2,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYL (1-3)] 2,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSIDE; 4,5 EPOXYPENTYL BETA DEXTRO GLUCOPYRANOSYL (1-3) BIS[BETA DEXTRP GLUCOPYRANOSYL (1-3)] BETA DEXTRO GLUCOPYRANOSIDE; 4,5 EPOXYPENTYL BETA DEXTRO GLUCOPYRANOSYL (1-3) TETRAKIS[BETA DEXTRO GLUCOPYRANOSYL (1-3)] BETA DEXTRO GLUCOPYRANOSIDE; 4,5 EPOXYPENTYL BETA DEXTRO GLUCOPYRANOSYL (1-3) TRIS[BETA DEXTRO GLUCOPYRANOSYL (1-3)] BETA DEXTRO GLUCOPYRANOSIDE; ALCOHOL; GLUCOSIDE; LEWIS ACID; OLIGOSACCHARIDE; PESTICIDE; PHYTOALEXIN; UNCLASSIFIED DRUG; EPOXIDE; PHYTOALEXINS; PLANT EXTRACT; TERPENE; VEGETABLE PROTEIN;

ACETYLATION; ARTICLE; BINDING AFFINITY; BIOASSAY; CATALYST; CONTROLLED STUDY; DEACETYLATION; EPOXIDATION; NONHUMAN; PHYTOCHEMISTRY; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN SYNTHESIS; BIOSYNTHESIS; METABOLISM; SYNTHESIS;

GLYCINE MAX;

EPOXY COMPOUNDS; GLUCOSIDES; OLIGOSACCHARIDES; PLANT EXTRACTS; PLANT PROTEINS; TERPENES;

EID: 13844309082     PISSN: 02820080     EISSN: 15734986     Source Type: Journal    
DOI: 10.1023/B:GLYC.0000038289.48502.0a     Document Type: Article

References (16)

1. Somssich IE, Hahlbrock K, Pathogen defense in plants - a praradigm of biological complexity, Trends Plant Sci 3, 86-90 (1998).
2. Boller J, Chemoperception of microbial signals in plant cells, Annual Review of Plant Physiology and Molecular Biology 46, 189-214 (1995).
3. Ebel J, Bhagwat AA, Cosio EG, Feger M, Kissel V, Mithǒfer A, Waldmǔller T, Elicitor-binding proteins and signal transduction in the activation of a phytoalexin defense response, Can. J. Bot 73, S506-10 (1994).
4. Hahn MG, Microbial elicitors and their receptors in plants, Annu. Rev. Phytopathol 34, 387-412 (1996).
5. Sharp JK, Valent B, Albersheim P, Purification and partial characterization of a beta-glucan fragment that elicits phytoalexin accumulation in soybean, J Biol Chem 259, 11312-20 (1984).
6. Raetz CRH, Biochemistry of endotoxins, Annu Rev Biochem 59, 129-70 (1990).
7. Legler G, Glycoside Hydrolases: Mechanistic information from studies with reversible and irreversible inhibitors, Adv Carbohydrate Chem Biochem 48, 319-84 (1990).
8. Chen L, Fincher GB, Høj PB, Evolution of polysaccharide hydrolase substrate specificity. Catalytic amino acids are conserved in barley 1,3-1,4- and 1,3-beta-glucanases, J Biol Chem 268, 13318-26 (1993).
9. Høj PB, Rodrigues EB, Iser JR, Stick RV, Stone BA, Active site-directed inhibition by optically pure epoxyalkyl cellobiosides reveals differences in active site geometry of two 1,3-1,4-beta-D-glucan 4-glucanohydrolases. The importance of epoxide stereochemistry for enzyme inactivation, J Biol Chem 266, 11628-31 (1991).
10. 3H]-4,5-epoxypentyl β-cellobioside: Synthesis of inhibitor and stoichiometry of interaction, Carbohydrate Research 188, 245-50 (1989).
11. Cheong J-J, Birberg W, Fugedi P, Pilotti A, Garegg PJ, Hong N, Ogawa T, Hahn MG, Structure-activity relationships of oligo-[beta]-glucoside elicitors of phytoalexin accumulation in soybean, The Plant Cell 3, 127-36 (1991).
12. Cosio EG, Frey T, Verduyn R, van Boom JH, Ebel J, High-affinity binding of a synthetic heptaglucoside and fungal glucan phytoalexin elicitors to soybean membranes. FEBS Lett 271, 223-26 (1990).
13. Cheong JJ, Hahn MG, A specific, high-affinity binding site for the hepta-[beta]-glucoside elicitor exists in soybean membranes, The Plant Cell 3, 137-47 (1991).
14. Cosio EG, Poepperl H, Schmidt W, Ebel J, High-affinity binding of fungal beta-glucan fragments to soybean (Glycine max L.) microsomal fractions and protoplasts, Eur J Biochem 175, 309-15 (1988).
15. Cosio EG, Frey T, Ebel J, Identification of a high-affinity binding protein for a hepta-beta-glucoside phytoalexin elicitor in soybean, Eur J Biochem 204, 1115-23 (1992).
16. Bradford MM, A rapid and sensitive method for the quantitation of microgam quantities of protein utilizing the principle of protein-dye bindhg, Anal Biochem 72, 248-54 (1976).