関: methylglyoxal

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/04/07 22:22:15」(JST)

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Methylglyoxal, also called pyruvaldehyde or 2-oxopropanal (CH₃-CO-CH=O or C₃H₄O₂) is the aldehyde form of pyruvic acid. It has two carbonyl groups, so it is a dicarbonyl compound. Methylglyoxal is both an aldehyde and a ketone.

In organisms, methylglyoxal is formed as a side-product of several metabolic pathways.^[1] It may form from 3-aminoacetone, which is an intermediate of threonine catabolism, as well as through lipid peroxidation. However, the most important source is glycolysis. Here, methylglyoxal arises from nonenzymatic phosphate elimination from glyceraldehyde phosphate and dihydroxyacetone phosphate, two intermediates of glycolysis. Since methylglyoxal is highly cytotoxic, the body developed several detoxification mechanisms. One of these is the glyoxalase system. Methylglyoxal reacts with glutathione to form a hemithioacetal. This is converted into S-D-lactoyl-glutathione by glyoxalase I,^[2] and then further metabolized into D-lactate by glyoxalase II.^[3]

Why methylglyoxal is produced remains unknown, but research indicates it may be involved in the formation of advanced glycation endproducts (AGEs).^[4] In this process, methylglyoxal reacts with free amino groups of lysine and arginine and with thiol groups of cysteine, forming AGEs. Recent research has identified heat shock protein 27 (Hsp27) as a specific target of posttranslational modification by methylglyoxal in human metastatic melanoma cells.^[5]

Other glycation agents include the reducing sugars:

glucose, the sugar that stores energy
galactose, a part of milk sugar (lactose)
allose, an all-cis hexose carried into the cell by special proteins
ribose, a component of RNA.

Due to increased blood glucose levels, methylglyoxal has higher concentrations in diabetics, and has been linked to arterial atherogenesis. Damage by methylglyoxal to low-density lipoprotein through glycation causes a fourfold increase of atherogenesis in diabetics.^[6]

Methylglyoxal has been suggested to be a better marker than carboxymethyllysine (CML) for investigating the association between AGEs with adverse health outcomes.

Recently one mechanism of activity in humans of methylglyoxal has been identified.^[7]^[8] Methylglyoxal binds directly to the nerves responsible for pain registration and by that increases pain sensation.

Methylglyoxal is the main active component of manuka honey and accounts for the majority of this honey's antimicrobial activity.^[9]

References

^ Inoue Y, Kimura A (1995). "Methylglyoxal and regulation of its metabolism in microorganisms". Adv. Microb. Physiol. Advances in Microbial Physiology 37: 177–227. doi:10.1016/S0065-2911(08)60146-0. ISBN 978-0-12-027737-7. PMID 8540421.
^ Thornalley PJ (2003). "Glyoxalase I—structure, function and a critical role in the enzymatic defence against glycation". Biochem. Soc. Trans. 31 (Pt 6): 1343–8. doi:10.1042/BST0311343. PMID 14641060.
^ Vander Jagt DL (1993). "Glyoxalase II: molecular characteristics, kinetics and mechanism". Biochem. Soc. Trans. 21 (2): 522–7. PMID 8359524.
^ Shinohara M; Thornalley, PJ; Giardino, I; Beisswenger, P; Thorpe, SR; Onorato, J; Brownlee, M (1998). "Overexpression of glyoxalase-I in bovine endothelial cells inhibits intracellular advanced glycation endproduct formation and prevents hyperglycemia-induced increases in macromolecular endocytosis". J Clin Invest. 101 (5): 1142–7. doi:10.1172/JCI119885. PMC 508666. PMID 9486985.
^ Bair WB 3rd, Cabello CM, Uchida K, Bause AS, Wondrak GT (April 2010). "GLO1 overexpression in human malignant melanoma". Melanoma Res 20 (2): 85–96. doi:10.1097/CMR.0b013e3283364903. PMC 2891514. PMID 20093988.
^ Rabbani N; Godfrey, L; Xue, M; Shaheen, F; Geoffrion, M; Milne, R; Thornalley, PJ (2011 May 26). "Glycation of LDL by methylglyoxal increases arterial atherogenicity. A possible contributor to increased risk of cardiovascular disease in diabetes". Diabetes 60 (7): 1973–80. doi:10.2337/db11-0085. PMC 3121424. PMID 21617182.
^ Spektrum: Diabetische Neuropathie: Methylglyoxal verstärkt den Schmerz: DAZ.online. Deutsche-apotheker-zeitung.de (2012-05-21). Retrieved on 2012-06-11.
^ Bierhaus, Angelika; Fleming, Thomas; Stoyanov, Stoyan; Leffler, Andreas; Babes, Alexandru; Neacsu, Cristian; Sauer, Susanne K; Eberhardt, Mirjam et al. (2012). "Methylglyoxal modification of Nav1.8 facilitates nociceptive neuron firing and causes hyperalgesia in diabetic neuropathy". Nature Medicine 18 (6): 926. doi:10.1038/nm.2750.
^ Kwakman PHS, te Velde AA, de Boer L, Vandenbroucke-Grauls CMJE, Zaat SAJ (2011). "Two major medicinal honeys have different mechanisms of bactericidal activity". PLoS ONE 6 (3): e17709. doi:10.1371/journal.pone.0017709. PMC 3048876. PMID 21394213.

English Journal

Heat-shock protein 27 (Hsp27) as a target of methylglyoxal in gastrointestinal cancer.

Oya-Ito T, Naito Y, Takagi T, Handa O, Matsui H, Yamada M, Shima K, Yoshikawa T.SourceDepartment of Medical Proteomics, Kyoto Prefectural University of Medicine, 465 Kaji-i, Kyoto 602-8566, Japan. oya-ito@koto.kpu-m.ac.jp
Biochimica et biophysica acta.Biochim Biophys Acta.2011 Jul;1812(7):769-81. Epub 2011 Apr 6.
The molecular mechanisms underlying the posttranslational modification of proteins in gastrointestinal cancer are still unknown. Here, we investigated the role of methylglyoxal modifications in gastrointestinal tumors. Methylglyoxal is a reactive dicarbonyl compound produced from cellular glycolytic
PMID 21497196

Catalytic conversion of dihydroxyacetone to lactic Acid using metal salts in water.

Rasrendra CB, Fachri BA, Makertihartha IG, Adisasmito S, Heeres HJ.SourceChemical Engineering Department, University of Groningen, Nijenborgh 4, 9747 AG Groningen (The Netherlands), Fax: (+31)?50 3634479; Chemical Engineering Department, Institut Teknologi Bandung, Ganesha 10 Bandung 40132 (Indonesia).
ChemSusChem.ChemSusChem.2011 Jun 20;4(6):768-77. doi: 10.1002/cssc.201000457. Epub 2011 May 20.
We herein present a study on the application of homogeneous catalysts in the form of metal salts on the conversion of trioses, such as dihydroxyacetone (DHA), and glyceraldehyde (GLY) to lactic acid (LA) in water. A wide range of metal salts (26 in total) were examined. Al(III) salts were identified
PMID 21598406

Japanese Journal

アルカリ水熱処理によるグリセリンからの乳酸生成反応の速度論的検討

岸田央範,金放鳴,守谷武彦,榎本兵治
化学工学論文集 32(6), 535-541, 2006-11-20
近年，化石燃料に換わる燃料として，バイオディーゼル燃料（BDF）が注目されている．しかし，BDFの製造時に約1/10の量のグリセリンが副生されるため，これの有効利用方法が課題となっている．著者らの研究の結果，グリセリンは，アルカリ性の高温高圧水中で，反応させることによって，乳酸に転換されることが分かった．乳酸への転換率は高く，300°C，90分の反応条件で，約90 mol%であった．また，反応経路 …
NAID 10018401903

Suppressive Effect of Trehalose on Acrylamide Formation from Asparagine and Reducing Saccharides

OKU Kazuyuki,KUROSE Mayumi,OGAWA Tohru,KUBOTA Michio,CHAEN Hiroto,FUKUDA Shigeharu,TSUJISAKA Yoshio
Bioscience, Biotechnology, and Biochemistry 69(8), 1520-1526, 2005
… Glucose is heat-degraded into pyruvaldehyde and 5-hydroxymethyl-2-furfural in the water system. …
NAID 130000030238

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リンク元	「ピルブアルデヒド」「methylglyoxal」

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Methylglyoxal
	IUPAC name 2-oxopropanal
Identifiers
CAS number	78-98-8
PubChem	880
ChemSpider	857
UNII	722KLD7415
DrugBank	DB03587
KEGG	C00546
MeSH	Methylglyoxal
ChEBI	CHEBI:17158
ChEMBL	CHEMBL170721
Jmol-3D images	Image 1
	SMILES CC(=O)C=O ;
	InChI InChI=1S/C3H4O2/c1-3(5)2-4/h2H,1H3 ; Key: AIJULSRZWUXGPQ-UHFFFAOYSA-N InChI=1/C3H4O2/c1-3(5)2-4/h2H,1H3; Key: AIJULSRZWUXGPQ-UHFFFAOYAZ ;
Properties
Molecular formula	C3H4O2
Molar mass	72.06 g mol−1
Related compounds
Related ketones, aldehydes	glyoxal; propionaldehyde; propanedial; acetone; diacetyl; acetylacetone
Related compounds	glyoxylic acid; pyruvic acid; acetoacetic acid
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references