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Escherichia coli K-12 substr. MG1655 Compound Class: xylan

Superclasses: all carbohydrates a carbohydrate a glycan a polysaccharide hemicellulose

Summary:
Xylan is a general name given for polysaccharides composed of xylose residues. It is the principal type of hemicellulose in plant biomass representing the second most abundant polysaccharide in the biosphere after cellulose [Schadel10].

The most common form of xylan is a (1→4)-β-D-xylan, which is found in the cell walls of plants and some algae. Pure (1→4)-β-D-xylan is uncommon. In most cases it is decorated with additional sugars, in the form of arabinoxylan, glucuronoxylan, glucuronoarabinoxylan or arabinoglucuronoxylan.

The secondary hydroxyl groups on xylose carbons 2 and 3 can be substituted by a number of residues, the type and degree of substitution depending on xylan's botanical source. Arabinose and glucuronic acid are linked to the backbone by glycosidic bonds. Other substituents form ester bonds: acetate groups are bound directly to the backbone, while cinnamoyl (feruloyl and coumaroyl) residues are linked to the side chain arabinoses [Joseleau92].

Due to its heterogeneous structure, the biodegradation of xylan requires the concerted action of a complex set of enzymes [Gordillo06]. These enzymes are mainly extracellular and are secreted by numerous fungi and bacteria [Biely85]. The endoxylanases and β xylosidases hydrolyze the main chain; the former generating short chain oligosaccharides and the latter acting on these products to liberate xylose. The side chains are hydrolyzed by glycanases, α-glucuronidases, acetyl xylan esterases and feruloyl esterases [deVries01].

(1->3)-β-D-xylan is found only in cell walls of some red and green algae.

Child Classes: a (1->3)-β-D-xylan (0) , a (1→4)-β-D-xylan (0) , a mix-linked (1→3/1→4)-β-D-xylan (0)

Unification Links: ChEBI:37166 , KEGG:C00707 , Wikipedia:Xylan

Reactions known to consume the compound:

Not in pathways:
xylan + n H2O → n α-D-xylopyranose

Credits:
Created 06-Jan-2011 by Kothari A , SRI International


References

Biely85: Biely P. (1985). "Microbial xylanolytic enzymes." Trends in Biotechnology.

Bochicchio03: Bochicchio, R., Reicher, F. (2003). "Are hemicelluloses from Podocarpus lambertii typical of gymnosperms?." Carbohydrate Polymers 53(2):127-136.

Carpita93: Carpita NC, Gibeaut DM (1993). "Structural models of primary cell walls in flowering plants: consistency of molecular structure with the physical properties of the walls during growth." Plant J 3(1);1-30. PMID: 8401598

deVries01: de Vries RP, Visser J (2001). "Aspergillus enzymes involved in degradation of plant cell wall polysaccharides." Microbiol Mol Biol Rev 65(4);497-522, table of contents. PMID: 11729262

Ebringerova05: Ebringerova, A., Hromadkova, Z., Heinze, T. (2005). "Hemicellulose." Adv Polym Sci 186:1-67.

Fukushi86: Fukushi, Y., Maeda, M. (1986). "Purification of xylan from the cell wall of Bryopsis maxima." Botanica Marina 29, 387-390.

Gordillo06: Gordillo F, Caputo V, Peirano A, Chavez R, Van Beeumen J, Vandenberghe I, Claeyssens M, Bull P, Ravanal MC, Eyzaguirre J (2006). "Penicillium purpurogenum produces a family 1 acetyl xylan esterase containing a carbohydrate-binding module: characterization of the protein and its gene." Mycol Res 110(Pt 10);1129-39. PMID: 17008082

Iriki60: Iriki Y, Suzuki T, Nisizawa K, Miwa T (1960). "Xylan of siphonaceous green algae." Nature 187;82-3. PMID: 13852998

Ishii97: Ishii, T. (1997). "Structure and functions of feruloylated polysaccharides." Plant Sci 127:11-127.

Joseleau92: Joseleau J. P., Comptat J., Ruel K. (1992). "Chemical structure of xylans and their interaction in the plant cell wall." Progress in Biotechnology.

Kiyohara06: Kiyohara M, Hama Y, Yamaguchi K, Ito M (2006). "Structure of beta-1,3-xylooligosaccharides generated from Caulerpa racemosa var. laete-virens beta-1,3-xylan by the action of beta-1,3-xylanase." J Biochem 140(3);369-73. PMID: 16891637

Lahaye03: Lahaye M, Rondeau-Mouro C, Deniaud E, Buleon A (2003). "Solid-state 13C NMR spectroscopy studies of xylans in the cell wall of Palmaria palmata (L. Kuntze, Rhodophyta)." Carbohydr Res 338(15);1559-69. PMID: 12860427

Mackie59: Mackie, I.M., Percival, E. (1959). "The constitution of xylan from the green seaweed Caulerpa filiformis." J. Chem. Soc. 1151-1158.

Polizeli05: Polizeli ML, Rizzatti AC, Monti R, Terenzi HF, Jorge JA, Amorim DS (2005). "Xylanases from fungi: properties and industrial applications." Appl Microbiol Biotechnol 67(5);577-91. PMID: 15944805

Schadel10: Schadel C, Richter A, Blochl A, Hoch G (2010). "Hemicellulose concentration and composition in plant cell walls under extreme carbon source-sink imbalances." Physiol Plant 139(3);241-55. PMID: 20113432

SchooneveldBerg99: Schooneveld-Bergmans, M.E. F., Dignum, M. J. W., Grabber, J. H.., Beldman, G., Voragen, A. G. J. (1999). "Studies on the oxidative cross-linking of feruloylated arabinoxylans from wheat flour and wheat bran." Carbohydrate Polymers 38:309-317.

Vignon98: Vignon, M. R., Gey, C. (1998). "Isolation, 1H and 13C NMR studies of (4-O-methyl-D-glucurono)-D-xylans from luffa fruit fibres, jute bast fibres and mucilage of quince tree seeds." Carbohydrate Research 307(1-2):107-111.

Yamagaki96: Yamagaki, T., Maeda, M., Kabazawa, K., Ishizuka, Y, Nakanishi, H. (1996). "Structures of Caulerpa cell wall microfibril xylan with detection of ?-1,3-xylooligosaccharides as revealed by matrix-assisted laser desorption ionization/time of flight/mass spectrometry." Biosci. Biotech. Biochem. 60, 1222-1228.


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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