同: glycerose

WordNet

a sweet crystalline aldehyde formed by the breakdown of sugars (同)glyceric aldehyde

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/11/20 08:01:12」(JST)

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Glyceraldehyde (glyceral) is a triose monosaccharide with chemical formula C₃H₆O₃. It is the simplest of all common aldoses. It is a sweet, colorless, crystalline solid that is an intermediate compound in carbohydrate metabolism. The word comes from combining glycerol and aldehyde, as glyceraldehyde is glycerol with one hydroxymethyl group oxidized to an aldehyde.

Structure

Glyceraldehyde has one chiral center and therefore exists as two different enantiomers with opposite optical rotation:

In the d/l nomenclature, either d from Latin Dexter meaning "right", or l from Latin Laevo meaning "left"
In the R/S nomenclature, either R from Latin Rectus meaning "right", or S from Latin Sinister meaning "left"

	d-glyceraldehyde (R)-glyceraldehyde (+)-glyceraldehyde	l-glyceraldehyde (S)-glyceraldehyde (−)-glyceraldehyde
Fischer projection
Skeletal formula
Ball-and-stick model

While the optical rotation of glyceraldehyde is (+) for R and (−) for L, this is not true for all monosaccharides. The stereochemical configuration can only be determined from the chemical structure, whereas the optical rotation can only be determined empirically (by experiment).

It was by a lucky guess that the molecular d- geometry was assigned to (+)-glyceraldehyde in the late 19th century, as confirmed by X-ray crystallography in 1951.^[2]

Nomenclature

In the d/l system, glyceraldehyde is used as the configurational standard for carbohydrates. Monosaccharides with an absolute configuration identical to (R)-glyceraldehyde at the last stereocentre, for example C5 in glucose, are assigned the stereo-descriptor d-. Those similar to (S)-glyceraldehyde are assigned an l-.

Chemical synthesis

Glyceraldehyde can be prepared, along with dihydroxyacetone, by the mild oxidation of glycerol, for example with hydrogen peroxide and a ferrous salt as catalyst. Dihydroxyacetone, the simplest ketose, is an isomer of glyceraldehyde.

Biosynthesis

The enzyme glycerol dehydrogenase (NADP⁺) has two substrates, glycerol and NADP⁺, and 3 products, D-glyceraldehyde, NADPH and H+.

Biochemical role

The interconversion of the phosphates of glyceraldehyde (glyceraldehyde 3-phosphate) and dihydroxyacetone (dihydroxyacetone phosphate), catalyzed by the enzyme triosephosphate isomerase, is an important intermediate step in glycolysis.

References

^ Merck Index, 11th Edition, 4376
^ Determination of the Absolute Configuration of Optically Active Compounds by Means of X-Rays Nature 168, 271-272 J. M. BIJVOET, A. F. PEERDEMAN & A. J. van BOMMEL doi:10.1038/168271a0

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English Journal

Determination of neutral diols and carboxylic acids formed during glycerol electrooxidation by capillary electrophoresis with dual C4D.

Teixeira WSR1, Santos MSF1, Gruber J1, Gutz IGR1, Lopes FS2.
Talanta.Talanta.2018 Feb 1;178:1040-1045. doi: 10.1016/j.talanta.2017.08.088. Epub 2017 Sep 1.
PMID 29136794

Acrolein: An Effective Biomarker for Tissue Damage Produced from Polyamines.

Igarashi K1,2, Uemura T3, Kashiwagi K4.
Methods in molecular biology (Clifton, N.J.).Methods Mol Biol.2018;1694:459-468. doi: 10.1007/978-1-4939-7398-9_38.
PMID 29080188

Bioanode with alcohol dehydrogenase undergoing a direct electron transfer on functionalized gold nanoparticles for an application in biofuel cells for glycerol conversion.

Ratautas D1, Tetianec L2, Marcinkevičienė L3, Meškys R3, Kulys J2.
Biosensors & bioelectronics.Biosens Bioelectron.2017 Dec 15;98:215-221. doi: 10.1016/j.bios.2017.06.048. Epub 2017 Jun 27.
PMID 28683414

Japanese Journal

Expression and characterization of an M cell-specific ligand-fused dengue virus tetravalent epitope using Saccharomyces cerevisiae (GENETICS, MOLECULAR BIOLOGY, AND GENE ENGINEERING)

Nguyen Ngoc-Luong,So Kum-Kang,Kim Jung-Mi [他],Kim Sae-Hae,Jang Yong-Suk,Yang Moon-Sik,Kim Dae-Hyuk
Journal of bioscience and bioengineering 119(1), 19-27, 2015-01
… The yeast episomal expression vector, pYEGPD-TER, which was designed to direct gene expression using the glyceraldehyde-3-phosphate dehydrogenase (GPD) promoter, a functional signal peptide of the amylase 1A protein from rice, and the GAL7 terminator, was used to clone the Tet-EDIII-Co1 gene and resultant plasmids were then used to transform Saccharomyces cerevisiae. …
NAID 110009892228

Evaluation of the Effect of Glyceraldehyde 3-phosphate Dehydrogenase on Heat-induced Myofibril Gels by Investigating Actin-myosin Interaction

, , , , ,
Food Science and Technology Research 21(1), 87-93, 2015
… In this study, the effect of glyceraldehyde 3-phosphate dehydrogenase (G3PD) on the molecular state of porcine myofibrils was investigated by observing the structural changes in myosin and actin in myofibrils using phase-contrast and fluorescence microscopy. …
NAID 130005061938

GAPDH-A Recruits a Plant Virus Movement Protein to Cortical Virus Replication Complexes to Facilitate Viral Cell-to-Cell Movement.

Kaido Masanori,Abe Kazutomo,Mine Akira,Hyodo Kiwamu,Taniguchi Takako,Taniguchi Hisaaki,Mise Kazuyuki,Okuno Tetsuro
PLoS pathogens 10(11), 2014-11
… One of these host proteins was glyceraldehyde 3-phosphate dehydrogenase-A (NbGAPDH-A), which is a component of the Calvin-Benson cycle in chloroplasts. …
NAID 120005522509

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拡張検索	「NAD-dependent glyceraldehyde-3-phosphate dehydrogenase」「glyceraldehyde 3-phosphate」

「NAD-dependent glyceraldehyde-3-phosphate dehydrogenase」

Glyceraldehyde
Names
	Systematic IUPAC name 2,3-Dihydroxypropanal
	Other names Glyceraldehyde; Glyceric aldehyde; Glyceral
Identifiers
CAS Number	56-82-6 (racemic) ; 453-17-8 (R) ; 497-09-6 (S) ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:5445 ;
ChemSpider	731 ;
ECHA InfoCard	100.006.088
PubChem CID	751;
UNII	DI19XSG16H (racemic) ; 41A680M0WB (R) ; GI7U82BL5A (S) ;
	InChI InChI=1S/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2 Key: MNQZXJOMYWMBOU-UHFFFAOYSA-N ; InChI=1/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2 Key: MNQZXJOMYWMBOU-UHFFFAOYAU ;
	SMILES O=CC(O)CO ; OCC(O)C=O ;
Properties
Chemical formula	C3H6O3
Molar mass	90.08 g·mol−1
Density	1.455 g/cm3
Melting point	145 °C (293 °F; 418 K)
Boiling point	140 to 150 at 0.8 mmHg
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

NAD依存性グリセルアルデヒド3リン酸脱水素酵素、NAD依存性グリセルアルデヒド3リン酸デヒドロゲナーゼ

「glyceraldehyde 3-phosphate」

　　[★] グリセルアルデヒド3-リン酸

[1] Merck Index, 11th Edition, 4376

[2] Determination of the Absolute Configuration of Optically Active Compounds by Means of X-Rays Nature 168, 271-272 J. M. BIJVOET, A. F. PEERDEMAN & A. J. van BOMMEL doi:10.1038/168271a0

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案内

案内

glyceraldehyde