WordNet

any monosaccharide sugar containing four atoms of carbon per molecule

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/05/07 14:27:26」(JST)

wiki en

A tetrose is a monosaccharide with 4 carbon atoms. They have either an aldehyde functional group in position 1 (aldotetroses) or a ketone functional group in position 2 (ketotetroses).^[1]^[2]

D-Erythrose
D-Threose
D-Erythrulose

The aldotetroses have two chiral centers ("asymmetric carbon atoms") and so 4 different stereoisomers are possible. There are two naturally occurring stereoisomers, the enantiomers of erythrose and threose having the D configuration but not the L enantiomers. The ketotetroses have one chiral center and, therefore, two possible stereoisomers: erythrulose (L- and D-form). Again, only the D enantiomer is naturally occurring.

References

^ Thisbe K. Lindhorst (2007). Essentials of Carbohydrate Chemistry and Biochemistry (1 ed ed.). Wiley-VCH. ISBN 3527315284.
^ John F. Robyt (1997). Essentials of Carbohydrate Chemistry (1 ed ed.). Springer. ISBN 0387949518.

This biochemistry article is a stub. You can help Wikipedia by expanding it.

English Journal

Synthesis of α-L-threose nucleoside phosphonates via regioselective sugar protection.

Dumbre SG, Jang MY, Herdewijn P.Author information Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium.AbstractA new synthesis route to α-L-threose nucleoside phosphonates via 2-O and 3-O selectively protected L-threose is developed. The key intermediates 2-O-benzoyl-L-threonolactone and 1-O-acetyl-2-O-benzoyl-3-O-t-butyldiphenylsilyl-L-threofuranose were functionalized to synthesize 2'-deoxy-2'-fluoro- and 3'-C-ethynyl L-threose 3'-O-phosphonate nucleosides. The key intermediates developed are important intermediates for the synthesis of new L-threose-based nucleoside analogues, TNA phosphoramidites, and TNA triphosphates.
The Journal of organic chemistry.J Org Chem.2013 Jul 19;78(14):7137-44. doi: 10.1021/jo400907g. Epub 2013 Jul 3.
A new synthesis route to α-L-threose nucleoside phosphonates via 2-O and 3-O selectively protected L-threose is developed. The key intermediates 2-O-benzoyl-L-threonolactone and 1-O-acetyl-2-O-benzoyl-3-O-t-butyldiphenylsilyl-L-threofuranose were functionalized to synthesize 2'-deoxy-2'-fluoro- and
PMID 23822647

Theoretical study of the mutarotation of erythrose and threose: acid catalysis.

Azofra LM, Alkorta I, Elguero J.Author information Instituto de Química Médica (I.Q.M.-C.S.I.C.), Juan de la Cierva, 3, E-28006 Madrid, Spain. luisazofra@iqm.csic.esAbstractThe acid catalysis of the mutarotation mechanism in the two aldotetroses, d-erythrose and d-threose, has been studied at B3LYP/6-311++G(d,p) computational level in gas phase and in solution employing the PCM-water model. The open-chain, the furanose and the connecting TS structures have been characterized. To study the enhancing effect of acid groups on the electrophilicity of the carbonyl carbon atom, four situations have been considered: (i) a classical Lewis acid as BH3; (ii) a classical hard-Pearson acid as Na(+); (iii) classical Brønsted acids as H(+) and H3O(+); and (iv) a combined strategy using H3O(+) and one bridge-H2O molecule as assistant in the proton transfer process. All the acidic groups reduce the activation energy with exception of the Na(+), which can act, in some cases, as inhibitor. It is greatly reduced by the presence of Brønsted acids (iii) and through the combined strategy (iv). For this last mechanism, the electronic activation energies are between 12 and 43 kJ mol(-1) in vacuum and between 13 and 25 kJ mol(-1) in water solution, through the use of the PCM model.
Carbohydrate research.Carbohydr Res.2013 May 3;372:1-8. doi: 10.1016/j.carres.2013.01.013. Epub 2013 Jan 29.
The acid catalysis of the mutarotation mechanism in the two aldotetroses, d-erythrose and d-threose, has been studied at B3LYP/6-311++G(d,p) computational level in gas phase and in solution employing the PCM-water model. The open-chain, the furanose and the connecting TS structures have been charact
PMID 23501397

Solution structure, dynamics and binding studies of a family 11 carbohydrate-binding module from Clostridium thermocellum (CtCBM11).

Viegas A, Sardinha J, Freire F, Duarte DF, Carvalho AL, Fontes CM, Romão MJ, Macedo AL, Cabrita EJ.Author information REQUIMTE-CQFB, Dep. de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal.AbstractNon-catalytic cellulosomal CBMs (carbohydrate-binding modules) are responsible for increasing the catalytic efficiency of cellulosic enzymes by selectively putting the substrate (a wide range of poly- and oligo-saccharides) and enzyme into close contact. In the present study we carried out an atomistic rationalization of the molecular determinants of ligand specificity for a family 11 CBM from thermophilic Clostridium thermocellum [CtCBM11 (C. thermocellum CBM11)], based on a NMR and molecular modelling approach. We have determined the NMR solution structure of CtCBM11 at 25°C and 50°C and derived information on the residues of the protein that are involved in ligand recognition and on the influence of the length of the saccharide chain on binding. We obtained models of the CtCBM11-cellohexaose and CtCBM11-cellotetraose complexes by docking in accordance with the NMR experimental data. Specific ligand-protein CH-π and Van der Waals interactions were found to be determinant for the stability of the complexes and for defining specificity. Using the order parameters derived from backbone dynamics analysis in the presence and absence of ligand and at 25°C and 50°C, we determined that the protein's backbone conformational entropy is slightly positive. This data in combination with the negative binding entropy calculated from ITC (isothermal titration calorimetry) studies supports a selection mechanism where a rigid protein selects a defined oligosaccharide conformation.
The Biochemical journal.Biochem J.2013 Apr 15;451(2):289-300. doi: 10.1042/BJ20120627.
Non-catalytic cellulosomal CBMs (carbohydrate-binding modules) are responsible for increasing the catalytic efficiency of cellulosic enzymes by selectively putting the substrate (a wide range of poly- and oligo-saccharides) and enzyme into close contact. In the present study we carried out an atomis
PMID 23356867

Japanese Journal

C-2 Epimer formation of tetrose, pentose and hexose sugars by xylose isomerase

VUOLANTO A.
Biocatal. Biotrans. 20, 235-240, 2002
NAID 30023025084

糖脂質酵素モデル (第9報) : 糖残基の立体配置の影響

大勝靖一,中村亘宏
日本油化学会誌 45(6), 537-543, 1996
ヘキソース, ペントース, およびテトロース型の糖脂質を用いてアミノ酸アミドを加水分解した。糖脂質としては, 親水性糖残基と疎水性残基の間に連結基としてチアゾリジン環を有するもの (間接型糖脂質) と有さないもの (直接型糖脂質) を使用した。一般に前者の糖脂質は後者のものよりも活性が高く, 基質識別能や加水分解活性のような活性は糖残基のC-2およびC-3位のヒドロキシル基の立体配置と関係のあるこ …
NAID 130001016504