関: calcium glycerophosphate

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/06/09 06:07:26」(JST)

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sn-Glycerol 3-phosphate^[1] is a phosphoric ester of glycerol, which is a component of glycerophospholipids. Equally appropriate names in biochemical context include glycero-3-phosphate, 3-O-phosphonoglycerol, 3-phosphoglycerol.^[2] From a historical reason, it is also known as L-glycerol 3-phosphate, D-glycerol 1-phosphate, L-α-glycerophosphoric acid.^[2] It should not be confused with the similarly named glycerate 3-phosphate or glyceraldehyde 3-phosphate.

Biosynthesis and metabolism

Glycerol 3-phosphate is synthesized by reducing dihydroxyacetone phosphate (DHAP), a glycolysis intermediate, with glycerol-3-phosphate dehydrogenase. DHAP and thus glycerol 3-phosphate is also possible to be synthesized from amino acids and citric acid cycle intermediates via glyconeogenesis pathway.

+ NAD(P)H + H⁺ → + NAD(P)⁺

It is also synthesized by phosphorylating glycerol generated upon hydrolyzing fats with glycerol kinase, and can feed into glycolysis or glyconeogenesis pathways.

+ ATP → + ADP

Glycerol 3-phosphate is a starting material for de novo synthesis of glycerolipids. In eukaryotes, it is first acylated on its sn-1 position by a ER- or mitochondrial membrane enzyme, glycerol-3-phosphate O-acyltransferase, and another acyl group is then added on the sn-2 position making phosphatidic acids.

+ Acyl-CoA → Lysophosphatidic acid + CoA

Some fungi have glycerol-1-phosphatase, which removes the phosphate group of glycerol 3-phosphate to generate glycerol. They can perform glycerol fermentation producing glycerol from glucose through glycolysis pathway.

+ H₂O → + Pi

Shuttle system

Glycerol-3-phosphate dehydrogenases are located both in the cytosol and the intermembrane face of mitochondrial inner membrane. Glycerol 3-phosphate (G3P) and dihydroxyacetone phosphate (DHAP) are so small molecule that they can permeate mitochondrial outer membrane through porins and shuttle between two dehydroganases. Using this shuttle system, NADH generated by cytosolic metabolisms including glycolysis are reoxidized to NAD⁺ reducing DHAP to G3P, and the reducing equivalent can be used for generating proton gradient across the mitochondrial inner membrane by coupling oxidizing G3P and reducing quinone.

Enantiomer

Glycerol 1-phosphate, sometimes called as D-glycerol 3-phosphate, is an enantiomer of glycerol 3-phosphate. Most organisms use 3-phosphate, or L-configuration, for glycerolipid backborn; however, 1-phosphate is specifically used in archeal ether lipids.

Notes

^ This article uses stereospecific numbering where stereoconfiguration is not explicitly specified.
^ ^a ^b G. P. Moss (ed.). "Nomenclature of Phosphorus-Containing Compounds of Biochemical Importance". Retrieved 2015-05-20.

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English Journal

Osteoblasts from a mandibuloacral dysplasia patient induce human blood precursors to differentiate into active osteoclasts.

Avnet S, Pallotta R, Perut F, Baldini N, Pittis MG, Saponari A, Lucarelli E, Dozza B, Greggi T, Maraldi NM, Capanni C, Mattioli E, Columbaro M, Lattanzi G.SourceLaboratory for Pathophysiology, Istituto Ortopedico Rizzoli, Bologna, Italy.
Biochimica et biophysica acta.2011 Jul;1812(7):711-8. Epub 2011 Mar 16.
Mandibuloacral dysplasia type A (MADA) is a rare disease caused by mutations in the LMNA gene encoding A type lamins. Patients affected by mandibuloacral dysplasia type A suffer from partial lipodystrophy, skin abnormalities and accelerated aging. Typical of mandibuloacral dysplasia type A is also b
PMID 21419220

Inorganic polymeric phosphate/polyphosphate as an inducer of alkaline phosphatase and a modulator of intracellular Ca(2+) level in osteoblasts (SaOS-2 cells) in vitro.

Muller WE, Wang X, Diehl-Seifert B, Kropf K, Schlosmacher U, Lieberwirth I, Glasser G, Wiens M, Schroder HC.SourceInstitute of Physiological Chemistry, University Medical Center of the Johannes Gutenberg University Mainz, Duesbergweg 6, D-55128 Mainz, Germany; NanotecMARIN GmbH, Duesbergweg 6, D-55128 Mainz, Germany.
Acta biomaterialia.2011 Jun;7(6):2661-2671. Epub 2011 Mar 30.
Inorganic polymeric phosphate is a physiological polymer that accumulates in bone cells. In the present study osteoblast-like SaOS-2 cells were exposed to this polymer, complexed in a 2:1 stoichiometric ratio with Ca(2+), polyP (Ca(2+) salt). At a concentration of 100μM, polyP (Ca(2+) salt) caused
PMID 21397057

Japanese Journal

Morinda citrifolia leaves enhance osteogenic differentiation and mineralization of human periodontal ligament cells

BOONANANTANASARN Kanitsak,JANEBODIN Kajohnkiart,SUPPAKPATANA Prapan,ARAYAPISIT Tawepong,RODSUTTHI Jit-aree,CHUNHABUNDIT Panjit,BOONANUNTANASARN Surintorn,SRIPAIROJTHIKOON Wanida
Dental materials journal 31(5), 863-871, 2012-09-01
… Human periodontal ligament cells were cultured in complete medium, ascorbic acid with β-glycerophosphate, or Morinda citrifolia leaf aqueous extract. … Morinda citrifolia leaf aqueous extract significantly increased alkaline phosphatase activity compared to culturing in complete medium or ascorbic acid with β-glycerophosphate. …
NAID 10030875941

Growth inhibitory effects of anthranilic acid and its derivatives against Legionella pneumophila(MICROBIAL PHYSIOLOGY AND BIOTECHNOLOGY)

Sasaki Takahide,Mizuguchi Satoru,Honda Kohsuke
Journal of bioscience and bioengineering 113(6), 726-729, 2012-06-00
… Although the growth of mutants deficient in anthranilate phosphoribosyltransferase (TrpD) and N-(5'-phosphoribosyl)anthranilate isomerase (TrpF) was not affected by exogenous anthranilic acid, the indole-3-glycerophosphate synthase (TrpC) deficient mutant exhibited an increased susceptibility compared with the parent strain. …
NAID 110009470593

Serum Glycerophosphate Levels are Increased in Japanese Men with Type 2 Diabetes

Daimon Makoto,Soga Tomoyoshi,Hozawa Atsushi,Oizumi Toshihide,Kaino Wataru,Takase Kaoru,Karasawa Shigeru,Jimbu Yumi,Wada Kiriko,Kameda Wataru,Susa Shinji,Kayama Takamasa,Saito Kaori,Tomita Masaru,Kato Takeo
Internal Medicine 51(6), 545-551, 2012
… The top-ranked metabolite was glycerol-3-phophate (glycerophosphate), which was significantly higher in subjects with diabetes than in those with NGT, even after Bonferroni correction for multiple testing (11.7±3.6 vs. 6.4±1.9 μM, respectively; … Stepwise multiple regression analyses revealed that serum glycerophosphate levels were significantly correlated with 2-h plasma glucose after a 75-g oral glucose tolerance test (r=0.553, p=0.0005), independently of other characteristics, including FPG and HbA1c. …
NAID 130002061932

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拡張検索	「calcium glycerophosphate」「sodium glycerophosphate」「glycerophosphate dehydrogenase」

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sn-Glycerol 3-phosphate
Names
	IUPAC name (R)-2,3-dihydroxypropyl dihydrogen phosphate
	Other names 1,2,3-propanetriol, 1-(dihydrogen phosphate), (2R)-; D-glycerol 1-phosphate; L-glycerol 3-phosphate; L-α-glycerophosphate; L-α-phosphoglycerol
Identifiers
CAS Registry Number	17989-41-2
	InChI InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m1/s1; Key: AWUCVROLDVIAJX-GSVOUGTGSA-N ;
Jmol-3D images	Image
KEGG	C00093
MeSH	Alpha-glycerophosphoric+acid
PubChem	439162
	SMILES C([C@H](COP(=O)(O)O)O)O ;
Properties
Chemical formula	C3H9O6P
Molar mass	172.074
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references