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MetaCyc Pathway: κ-carrageenan degradation

Enzyme View:

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: Degradation/Utilization/Assimilation Carbohydrates Degradation Polysaccharides Degradation Carrageenan Degradation
Degradation/Utilization/Assimilation Polymeric Compounds Degradation Polysaccharides Degradation Carrageenan Degradation

Some taxa known to possess this pathway include ? : Coraliomargarita akajimensis DSM 45221 [Mavromatis10], Pseudoalteromonas carrageenovora [Johston73], Pseudoalteromonas sp. AJ5 [Ma08a], Pseudoalteromonas sp. LL1 , Rhodopirellula baltica [Glockner03], Zobellia galactanivorans [Barbeyron98]

Expected Taxonomic Range: Bacteria

Summary:
General Background

Carrageenans and carrageenoses are sulfated polysaccharides that are extracted from sea weeds belonging to the Rhodophyta (red algae), mainly from Chondrus crispus, and species from the Eucheuma and Gigartina genera. They are laid out in the cell wall at a high density and can constitute up to 50% of the algae dry mass.

The basic units of carrageenans are repeats of alternating β -1,3 linked D-galactose and α-1,4- linked D-galactose units, which are often substituted by sulfate. Carrageenans are classified according to the number and the position of sulfated ester [Matsuhiro92].

In carrageenoses the α-1,4- linked galactose units are modified by having a 3,6 - anhydro bridge. These bridges, which form a double helix during aggregation, are responsible for the gelation that is typical to these compounds. Despite this distinction, carrageenoses are often referred to as carrageenans.

The three most industrially exploited carrageenans, namely, κ-carrageenose, ι-carrageenose and λ-carrageenan, are distinguished by the presence of one, two or three ester-sulfate groups per repeating disaccharide unit respectively.

κ-carrageenose is sulfated only at position 4 of the β -1,3 linked D-galactose units.

About This Pathway

Carrageenans constitute a crucial carbon source for a number of marine bacteria. These organisms, which belong mainly to the classes Gammaproteobacteria, Flavobacteria and Sphingobacteria, degrade the cell walls of marine red algae by secreting specific glycoside hydrolases known as carrageenases.

The marine bacterium Pseudoalteromonas carrageenovora produces an endo-cleaving enzyme that attacks the (1→4)-β-D-linkages between D-galactose 4-sulfate and 3,6-anhydro-D-galactose in κ-carrageenans, producing the disaccharide neocarrabiose sulfate and the tetrasaccharide neocarratetraose 4-O-disulfate as the main products with retention of the anomeric configuration [Weigl66, McLean79]. One of the sulfate groups of the tetraose is removed by the bifunctional enzyme neocarrabiose sulfate/neotetraose disulfate 4-sulfatase, generating neocarratetraose 4-O-sulfate [McLean79a], which is cleaved by neocarratetraose 4-O-monosulfate β-hydrolase to neocarrabiose sulfate and neocarrabiose [McLean81]. Finally, the second sulfate group is then removed from neocarrabiose sulfate by neocarrabiose sulfate/neotetraose disulfate 4-sulfatase, leaving neocarrabiose as the sole product [Weigl66a].

Credits:
Created 14-Jun-2011 by Caspi R , SRI International


References

Barbeyron98: Barbeyron T, Gerard A, Potin P, Henrissat B, Kloareg B (1998). "The kappa-carrageenase of the marine bacterium Cytophaga drobachiensis. Structural and phylogenetic relationships within family-16 glycoside hydrolases." Mol Biol Evol 15(5);528-37. PMID: 9580981

Glockner03: Glockner FO, Kube M, Bauer M, Teeling H, Lombardot T, Ludwig W, Gade D, Beck A, Borzym K, Heitmann K, Rabus R, Schlesner H, Amann R, Reinhardt R (2003). "Complete genome sequence of the marine planctomycete Pirellula sp. strain 1." Proc Natl Acad Sci U S A 100(14);8298-303. PMID: 12835416

Guibet06: Guibet M, Kervarec N, Genicot S, Chevolot Y, Helbert W (2006). "Complete assignment of 1H and 13C NMR spectra of Gigartina skottsbergii lambda-carrageenan using carrabiose oligosaccharides prepared by enzymatic hydrolysis." Carbohydr Res 341(11);1859-69. PMID: 16716278

Johston73: Johston KH, McCandless EL (1973). "Enzymic hydrolysis of the potassium chloride soluble fraction of carrageenan: properties of "lambda carrageenases" from Pseudomonas carrageenovora." Can J Microbiol 19(7);779-88. PMID: 4727801

Ma08a: Ma Y, Dong S, Liu S, Mou H, Jiang X (2008). "Optimization of kappa-carrageenase production by Pseudoalteromonas sp. AJ5." Wei Sheng Wu Xue Bao 48(6);757-64. PMID: 18720840

Matsuhiro92: Matsuhiro B, Urzua CC (1992). "Heterogeneity of carrageenans from Chondrus crispus." Phytochemistry 31(2);531-4. PMID: 1367970

Mavromatis10: Mavromatis K, Abt B, Brambilla E, Lapidus A, Copeland A, Deshpande S, Nolan M, Lucas S, Tice H, Cheng JF, Han C, Detter JC, Woyke T, Goodwin L, Pitluck S, Held B, Brettin T, Tapia R, Ivanova N, Mikhailova N, Pati A, Liolios K, Chen A, Palaniappan K, Land M, Hauser L, Chang YJ, Jeffries CD, Rohde M, Goker M, Bristow J, Eisen JA, Markowitz V, Hugenholtz P, Klenk HP, Kyrpides NC (2010). "Complete genome sequence of Coraliomargarita akajimensis type strain (04OKA010-24)." Stand Genomic Sci 2(3);290-9. PMID: 21304713

McLean79: McLean MW, Williamson FB (1979). "kappa-Carrageenase from Pseudomonas carrageenovora." Eur J Biochem 93(3);553-8. PMID: 33808

McLean79a: McLean MW, Williamson FB (1979). "Glycosulphatase from Pseudomonas carrageenovora. Purification and some properties." Eur J Biochem 101(2);497-505. PMID: 520310

McLean81: McLean MW, Williamson FB (1981). "Neocarratetraose 4-O-monosulphate beta-hydrolase from Pseudomonas carrageenovora." Eur J Biochem 113(3);447-56. PMID: 7215336

Weigl66: Weigl J, Yaphe W (1966). "The enzymic hydrolysis of carrageenan by Pseudomonas carrageenovora: purification of a kappa-carrageenase." Can J Microbiol 12(5);939-47. PMID: 5972647

Weigl66a: Weigl, J., Yaphe, W. (1966). "Glycosulfatase of Pseudomonas carrageenovora. Desulfation of disaccharide from κ-carrageenan." Canadian J. of Microbiol. 12:874-876.

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Barbeyron94: Barbeyron T, Henrissat B, Kloareg B (1994). "The gene encoding the kappa-carrageenase of Alteromonas carrageenovora is related to beta-1,3-1,4-glucanases." Gene 139(1);105-9. PMID: 8112578

Falshaw05: Falshaw R, Furneaux RH, Stevenson DE (2005). "Structural analysis of carrageenans from the red alga, Callophyllis hombroniana Mont. Kutz (Kallymeniaceae, Rhodophyta)." Carbohydr Res 340(6);1149-58. PMID: 15797130

GalperinLemaitr75: Galperin-Lemaitre H, Kirsch-Volders M, Levi S (1975). "Letter: Ultrasound and mammalian D.N.A." Lancet 2(7936);662. PMID: 52031

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Michel01: Michel G, Chantalat L, Duee E, Barbeyron T, Henrissat B, Kloareg B, Dideberg O (2001). "The kappa-carrageenase of P. carrageenovora features a tunnel-shaped active site: a novel insight in the evolution of Clan-B glycoside hydrolases." Structure 9(6);513-25. PMID: 11435116

Michel99: Michel G, Barbeyron T, Flament D, Vernet T, Kloareg B, Dideberg O (1999). "Expression, purification, crystallization and preliminary x-ray analysis of the kappa-carrageenase from Pseudoalteromonas carrageenovora." Acta Crystallogr D Biol Crystallogr 55(Pt 4);918-20. PMID: 10089334

Potin95: Potin P, Richard C, Barbeyron T, Henrissat B, Gey C, Petillot Y, Forest E, Dideberg O, Rochas C, Kloareg B (1995). "Processing and hydrolytic mechanism of the cgkA-encoded kappa-carrageenase of Alteromonas carrageenovora." Eur J Biochem 228(3);971-5. PMID: 7737202


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Wed Nov 26, 2014, BIOCYC13A.