|Superclasses:||all carbohydrates → a carbohydrate → a glycan → a polysaccharide → hemicellulose|
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.
Reactions known to consume the compound:
Not in pathways:
a polysaccharide + H2O → an oligosaccharide
Reactions known to produce the compound:
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
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
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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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