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MetaCyc Pathway: glycine betaine biosynthesis III (plants)

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.

Synonyms: glycine betaine biosynthesis

Superclasses: Biosynthesis Amines and Polyamines Biosynthesis Betaine Biosynthesis

Some taxa known to possess this pathway include ? : Arabidopsis thaliana col , Spinacia oleracea

Expected Taxonomic Range: Viridiplantae

Summary:
General Background

Glycine betaine (N,N,N-trimethylglycine) is a very efficient osmolyte found in a wide range of bacteria and plants, where it is accumulated at high cytoplasmic concentrations in response to osmotic stress, to act as an osmoprotectant. In addition to its osmoprotectant activity, glycine betaine is also a potent protectant against mutagenic compounds [Ji03, Monobe05] and radiation-induced damage [Monobe03].

Glycine betaine can either be taken up directly from the environment, or synthesized. A common biosynthesis pathway for glycine betaine is from choline, utilizing a two-step pathway with betaine aldehyde as intermediate. This pathway is conserved in bacteria and plants, but shows divergence in the enzymes involved. Gram-negative bacteria, Gram-positive bacteria and higher plants all use a betaine aldehyde dehydrogenase (EC 1.2.1.8) to catalyze the conversion of betaine aldehyde to glycine betaine. The choline-to-betaine aldehyde reaction, however, is divergent: Gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa, and Sinorhizobium meliloti utilize a choline dehydrogenase (EC 1.1.99.1) (see glycine betaine biosynthesis I (Gram-negative bacteria)), Gram-positive bacteria, such as Bacillus subtilis, use an alcohol dehydrogenase (EC 1.1.1.1) (see glycine betaine biosynthesis II (Gram-positive bacteria)), while high plants use a choline monooxygenase (EC 1.14.15.7) (this pathway).

Certain Gram-positive bacteria, such as Arthrobacter pascens and Arthrobacter globiformis, as well as the fungus Cylindrocarpon didymun, use yet another enzyme to catalyze this conversion: they use a soluble choline oxidase that catalyzes both steps (see choline degradation II).

There exists at least one more variation for the synthesis of glycine betaine, which is found in several halotolerant bacteria. The pathway was found in Halorhodospira halochloris (previously known as Ectothiorhodospira halochloris) and several other organisms, which synthesize glycine betaine from glycine through a series of methylation reactions [Nyyssola00] (see glycine betaine biosynthesis IV (from glycine)). However, since methylation reactions are among the most energy-consuming processes in nature (the regeneration of one active methyl group of S-adenosylmethionine costs the cell 12 ATP equivalents), it is not surprising that this pathway is less common.

About This Pathway

Glycine betain biosynthesis in plants differs from that in bacteria and animal. Plants convert choline to betaine aldehyde by the activity of choline monooxygenase, a Rieske type iron-sulfur-containing enzyme, whereas bacteria and animals catalyze this reaction utilizing either choline dehydrogenase or choline oxidase.

The two enzymes of this pathway have been characterized in plants including spinach and sugar beet. Arabidopsis is generally considered a non-glycine betaine accumulating plant [Hibino02], yet data suggests the endogenous glycine betaine level can be induced by cold acclimation and water stress [Xing01].

Citations: [Burnet95]

Variants: β-alanine betaine biosynthesis , choline degradation I , choline-O-sulfate degradation , glycine betaine biosynthesis I (Gram-negative bacteria) , glycine betaine biosynthesis II (Gram-positive bacteria) , glycine betaine biosynthesis IV (from glycine) , glycine betaine biosynthesis V (from glycine)

Unification Links: AraCyc:PWY1F-353


References

Burnet95: Burnet M, Lafontaine PJ, Hanson AD (1995). "Assay, Purification, and Partial Characterization of Choline Monooxygenase from Spinach." Plant Physiol 108(2);581-588. PMID: 12228495

Hibino02: Hibino T, Waditee R, Araki E, Ishikawa H, Aoki K, Tanaka Y, Takabe T (2002). "Functional characterization of choline monooxygenase, an enzyme for betaine synthesis in plants." J Biol Chem 277(44);41352-60. PMID: 12192001

Ji03: Ji C, Kaplowitz N (2003). "Betaine decreases hyperhomocysteinemia, endoplasmic reticulum stress, and liver injury in alcohol-fed mice." Gastroenterology 124(5);1488-99. PMID: 12730887

Monobe03: Monobe M, Koike S, Uzawa A, Ando K (2003). "Effects of beer administration in mice on acute toxicities induced by X rays and carbon ions." J Radiat Res (Tokyo) 44(1);75-80. PMID: 12841603

Monobe05: Monobe M, Uzawa A, Hino M, Ando K, Kojima S (2005). "Glycine betaine, a beer component, protects radiation-induced injury." J Radiat Res (Tokyo) 46(1);117-21. PMID: 15802867

Nyyssola00: Nyyssola A, Kerovuo J, Kaukinen P, von Weymarn N, Reinikainen T (2000). "Extreme halophiles synthesize betaine from glycine by methylation." J Biol Chem 2000;275(29);22196-201. PMID: 10896953

Xing01: Xing W, Rajashekar CB (2001). "Glycine betaine involvement in freezing tolerance and water stress in Arabidopsis thaliana." Environ Exp Bot 46(1);21-28. PMID: 11378169

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

Boch97: Boch J, Nau-Wagner G, Kneip S, Bremer E (1997). "Glycine betaine aldehyde dehydrogenase from Bacillus subtilis: characterization of an enzyme required for the synthesis of the osmoprotectant glycine betaine." Arch Microbiol 168(4);282-9. PMID: 9297465

Boyd91: Boyd LA, Adam L, Pelcher LE, McHughen A, Hirji R, Selvaraj G (1991). "Characterization of an Escherichia coli gene encoding betaine aldehyde dehydrogenase (BADH): structural similarity to mammalian ALDHs and a plant BADH." Gene 103(1);45-52. PMID: 1879697

BRENDA14: BRENDA team (2014). "Imported from BRENDA version existing on Aug 2014." http://www.brenda-enzymes.org.

Brocker10: Brocker C, Lassen N, Estey T, Pappa A, Cantore M, Orlova VV, Chavakis T, Kavanagh KL, Oppermann U, Vasiliou V (2010). "Aldehyde dehydrogenase 7A1 (ALDH7A1) is a novel enzyme involved in cellular defense against hyperosmotic stress." J Biol Chem 285(24);18452-63. PMID: 20207735

Falkenberg90: Falkenberg P, Strom AR (1990). "Purification and characterization of osmoregulatory betaine aldehyde dehydrogenase of Escherichia coli." Biochim Biophys Acta 1990;1034(3);253-9. PMID: 2194570

Gell02: Gell D, Kong Y, Eaton SA, Weiss MJ, Mackay JP (2002). "Biophysical characterization of the alpha-globin binding protein alpha-hemoglobin stabilizing protein." J Biol Chem 277(43);40602-9. PMID: 12192002

Gruez04: Gruez A, Roig-Zamboni V, Grisel S, Salomoni A, Valencia C, Campanacci V, Tegoni M, Cambillau C (2004). "Crystal structure and kinetics identify Escherichia coli YdcW gene product as a medium-chain aldehyde dehydrogenase." J Mol Biol 343(1);29-41. PMID: 15381418

Incharoensakdi00: Incharoensakdi A, Matsuda N, Hibino T, Meng YL, Ishikawa H, Hara A, Funaguma T, Takabe T, Takabe T (2000). "Overproduction of spinach betaine aldehyde dehydrogenase in Escherichia coli. Structural and functional properties of wild-type, mutants and E. coli enzymes." Eur J Biochem 267(24);7015-23. PMID: 11106411

Ishitani95: Ishitani M, Nakamura T, Han SY, Takabe T (1995). "Expression of the betaine aldehyde dehydrogenase gene in barley in response to osmotic stress and abscisic acid." Plant Mol Biol 27(2);307-15. PMID: 7888620

Lambou13: Lambou K, Pennati A, Valsecchi I, Tada R, Sherman S, Sato H, Beau R, Gadda G, Latge JP (2013). "Pathway of glycine betaine biosynthesis in Aspergillus fumigatus." Eukaryot Cell 12(6);853-63. PMID: 23563483

Landfald86: Landfald B, Strom AR (1986). "Choline-glycine betaine pathway confers a high level of osmotic tolerance in Escherichia coli." J Bacteriol 1986;165(3);849-55. PMID: 3512525

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

Lerma88: Lerma C, Hanson AD, Rhodes D (1988). "Oxygen-18 and deuterium labeling studies of choline oxidation by spinach and sugar beet." Plant Physiol 88(3);695-702. PMID: 16666370

Missihoun11: Missihoun TD, Schmitz J, Klug R, Kirch HH, Bartels D (2011). "Betaine aldehyde dehydrogenase genes from Arabidopsis with different sub-cellular localization affect stress responses." Planta 233(2);369-82. PMID: 21053011

Mou02: Mou Z, Wang X, Fu Z, Dai Y, Han C, Ouyang J, Bao F, Hu Y, Li J (2002). "Silencing of phosphoethanolamine N-methyltransferase results in temperature-sensitive male sterility and salt hypersensitivity in Arabidopsis." Plant Cell 14(9);2031-43. PMID: 12215503

Osteras98: Osteras M, Boncompagni E, Vincent N, Poggi MC, Le Rudulier D (1998). "Presence of a gene encoding choline sulfatase in Sinorhizobium meliloti bet operon: choline-O-sulfate is metabolized into glycine betaine." Proc Natl Acad Sci U S A 1998;95(19);11394-9. PMID: 9736747

Park06: Park YJ, Yoo CB, Choi SY, Lee HB (2006). "Purifications and characterizations of a ferredoxin and its related 2-oxoacid:ferredoxin oxidoreductase from the hyperthermophilic archaeon, Sulfolobus solfataricus P1." J Biochem Mol Biol 39(1);46-54. PMID: 16466637

Pocard97: Pocard JA, Vincent N, Boncompagni E, Smith LT, Poggi MC, Le Rudulier D (1997). "Molecular characterization of the bet genes encoding glycine betaine synthesis in Sinorhizobium meliloti 102F34." Microbiology 1997;143 ( Pt 4);1369-79. PMID: 9141699

Rathinasabapath97: Rathinasabapathi B, Burnet M, Russell BL, Gage DA, Liao PC, Nye GJ, Scott P, Golbeck JH, Hanson AD (1997). "Choline monooxygenase, an unusual iron-sulfur enzyme catalyzing the first step of glycine betaine synthesis in plants: prosthetic group characterization and cDNA cloning." Proc Natl Acad Sci U S A 94(7);3454-8. PMID: 9096415

Weretilnyk88: Weretilnyk EA, Hanson AD (1988). "Betaine aldehyde dehydrogenase polymorphism in spinach: genetic and biochemical characterization." Biochem Genet 26(1-2);143-51. PMID: 3377756

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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, biocyc13.