関: erythrose

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/08/13 21:14:43」(JST)

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Threose is a four-carbon monosaccharide or carbohydrate with molecular formula C₄H₈O₄. It has a terminal aldehyde group rather than a ketone in its linear chain, and so is considered part of the aldose family of monosaccharides. The threose name can be used to refer to both the D- and L-stereoisomers, and more generally to the racemic mixture (D/L-, equal parts D- and L-) as well as to the more generic threose structure (absolute stereochemistry unspecified).

The prefix "threo" which derives from threose (and "erythro" from a corresponding diastereomer erythrose) offer a useful way to describe general organic structures with adjacent chiral centers, where "the prefixes... designate the relative configuration of the centers".^[2] As is depicted in a Fischer projection of D-threose, the adjacent substituents will have a syn orientation in the isomer referred to as "threo", and are anti in the isomer referred to as "erythro".^[3]

Fischer projections depicting the two enantiomers of threose

References

^ Merck Index, 11th Edition, 9317
^ Formulas Using Other Configurational Notations, W. Rausch, accessed 1 March 2011
^ ibid. Prof. Rausch helpfully notes that the prefixes "may be applied to racemic compounds, as well as pure enantiomers and meso compounds", and that when depicted in the common "zig-zag" representation, adjacent "substituents may lie on the same side of the carbon chain... [syn] or on opposite sides... [anti]", which is opposite of their depiction in a Fischer projection.

English Journal

PhDAHP1 is required for floral volatile benzenoid/phenylpropanoid biosynthesis in Petunia × hybrida cv 'Mitchell Diploid'.

Langer KM1, Jones CR1, Jaworski EA1, Rushing GV1, Kim JY1, Clark DG1, Colquhoun TA2.
Phytochemistry.Phytochemistry.2014 Jul;103:22-31. doi: 10.1016/j.phytochem.2014.04.004. Epub 2014 May 6.
Floral volatile benzenoid/phenylpropanoid (FVBP) biosynthesis consists of numerous enzymatic and regulatory processes. The initial enzymatic step bridging primary metabolism to secondary metabolism is the condensation of phosphoenolpyruvate (PEP) and erythrose-4-phosphate (E4P) carried out via 3-DEO
PMID 24815009

GPI/AMF inhibition blocks the development of the metastatic phenotype of mature multi-cellular tumor spheroids.

Gallardo-Pérez JC1, Rivero-Segura NA1, Marín-Hernández A1, Moreno-Sánchez R1, Rodríguez-Enríquez S2.
Biochimica et biophysica acta.Biochim Biophys Acta.2014 Jun;1843(6):1043-53. doi: 10.1016/j.bbamcr.2014.01.013. Epub 2014 Jan 16.
Epithelial-mesenchymal transition (EMT) and cellular invasiveness are two pivotal processes for the development of metastatic tumor phenotypes. The metastatic profile of non-metastatic MCF-7 cells growing as multi-cellular tumor microspheroids (MCTSs) was analyzed by determining the contents of the
PMID 24440856

Non-enzymatic glycolysis and pentose phosphate pathway-like reactions in a plausible Archean ocean.

Keller MA1, Turchyn AV, Ralser M.
Molecular systems biology.Mol Syst Biol.2014 Apr 25;10:725. doi: 10.1002/msb.20145228.
The reaction sequences of central metabolism, glycolysis and the pentose phosphate pathway provide essential precursors for nucleic acids, amino acids and lipids. However, their evolutionary origins are not yet understood. Here, we provide evidence that their structure could have been fundamentally
PMID 24771084

Japanese Journal

Cloning, Expression, and Transcription Analysis of L-Arabinose Isomerase Gene from Mycobacterium smegmatis SMDU

Takata Goro,Poonperm Wayoon,Rao Devendar [他],SOUDA Akane,NISHIZAKI Tomoe,MORIMOTO Kenji,IZUMORI Ken
Bioscience, biotechnology, and biochemistry 71(12), 2876-2885, 2007-12-23
… Although the recombinant L-AI showed high substrate specificity, as did L-AI from other organisms, this enzyme catalyzed not only isomerization of L-arabinose-L-ribulose and D-galactose-D-tagatose but also isomerization of L-altrose-L-psicose and L-erythrulose-L-threose. … smegmatis</I>, L-threose and L-altrose can be produced from cheap and abundant erythritol and D-fructose respectively, indicating that this enzyme has great potential for biological application in rare sugar production. …
NAID 10027521659

Purification and Characterization of Sea Squirt α-N-Acetylgalactosaminidase

Shigeta Seiko,Suzuki Osamu,Aki Yasuhiro [他],KAWAMOTO SEIJI,ONO KAZUHISA
Journal of bioscience and bioengineering 89(1), 84-86, 2000-01-25
… Furthermore, an allergenic pentasaccharitol ABEE derivative, GalNAcα1→2Fucα1→3(GalNAcβ1→4) GlcNAcβ1→2(3-acetoamido-3-deoxy)_L-threose-ABEE, the minimum structural unit for the sea squirt allergenicity was hydrolyzed to 95 mol% for 72 h incubation with the enzyme. …
NAID 110002684498

52 光学活性キノカルシンの合成研究(口頭発表の部)

加藤正,新井かつ子,相原淳子,斉藤昭一,田中克典,中谷和彦,松田冬彦,寺島孜郎
天然有機化合物討論会講演要旨集 (34), 400-407, 1992-09-10
… For construction of the A B E ring system(10), crucial reduction of 6 derived from the anisole(13) and the D-threose derivative(5) with sodium cyanoborohydride was found to proceed in a highly diastereoselective manner to afford the tetrahydroiso-quinoline(15) as a sole product. … By employing the L-threose derivative(ent- 5) instead of 5, ent- 10 could be similarly produced by way of ent- 15. …
NAID 110006679113

「erythrose」

Threose
	; D-Threose
	; L-Threose
	IUPAC name (2S,3R)-2,3,4-Trihydroxybutanal (D); (2R,3S)-2,3,4-Trihydroxybutanal (L)
	Other names Threotetrose
Identifiers
CAS number	95-43-2 (D) , 95-44-3 (L)
PubChem	439665 (D)
ChemSpider	388736
ChEBI	CHEBI:28587
Jmol-3D images	Image 1; Image 2
	SMILES O=C[C@@H](O)[C@H](O)CO (D) OC[C@H](O)[C@@H](O)C=O (L) ;
	InChI InChI=1S/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4-/m1/s1 ; Key: YTBSYETUWUMLBZ-QWWZWVQMSA-N InChI=1/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4-/m1/s1; Key: YTBSYETUWUMLBZ-QWWZWVQMBY ;
Properties
Molecular formula	C4H8O4
Molar mass	120.10 g mol−1
Appearance	Syrup
Solubility in water	Very soluble
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references

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エリトロース、エリスロース

関: threose

「トレオース」

　　[★]

英: threose
関: エリトロース

[1] Merck Index, 11th Edition, 9317

[2] Formulas Using Other Configurational Notations, W. Rausch, accessed 1 March 2011

[3] . Prof. Rausch helpfully notes that the prefixes "may be applied to racemic compounds, as well as pure enantiomers and meso compounds", and that when depicted in the common "zig-zag" representation, adjacent "substituents may lie on the same side of the carbon chain... [syn] or on opposite sides... [anti]", which is opposite of their depiction in a Fischer projection.

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案内

threose