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Xylose (cf. Greek ξύλον, xylon, "wood") is a sugar first isolated from wood, and named for it. Xylose is classified as a monosaccharide of the aldopentose type, which means that it contains five carbon atoms and includes a formyl functional group. It is derived from hemicellulose, one of the main constituents of biomass. Like most sugars, it can adopt several structures depending on conditions. With its free carbonyl group, it is a reducing sugar.

Structure

The acyclic form of xylose has chemical formula HOCH₂(CH(OH))₃CHO. The cyclic hemiacetal isomers are more prevalent in solution and are of two types: the pyranoses, which feature six-membered C₅O rings, and the furanoses, which feature five-membered C₄O rings (with a pendant CH₂OH group). Each of these rings subject to further isomerism, depending on the relative orientation of the anomeric hydroxy group.

Occurrence

Xylose is the main building block for the hemicellulose xylan, which comprises about 30% of some plants (birch for example), far less in others (spruce and pine have about 9% xylan). Xylose is otherwise pervasive, being found in the embryos of most edible plants. It was first isolated from wood by Finnish scientist, Koch, in 1881,^[3] but first became commercially viable, with a price close to sucrose, in 1930.^[4]

Xylose is also the first saccharide added to the serine or threonine in the proteoglycan type O-glycosylation, and, so, it is the first saccharide in biosynthetic pathways of most anionic polysaccharides such as heparan sulfate and chondroitin sulfate.^[5]

Applications

Chemicals

The acid-catalysed degradation of hemicellulose gives furfural,^[6] a specialty solvent in industry and a precursor to synthetic polymers.^[7]

Human consumption

Xylose is metabolised by humans, though it is not a major human nutrient and largely excreted by the kidneys.^[8] Humans must obtain xylose from their diet. An oxido-reductase pathway is present in eukaryotic microorganisms. Humans have an enzyme called xylosyltransferase, which transfers xylose from UDP to a serine in the core protein of proteoglycans.^{[citation needed]}

Xylose contains 0 calories per gram.^[9]

Animal medicine

In animal medicine, xylose is used to test for malabsorption by administration in water to the patient after fasting. If xylose is detected in blood and/or urine within the next few hours, it has been absorbed by the intestines.^[10]

High xylose intake on the order of approximately 100g/kg of animal body weight is relatively well tolerated in pigs, and in a similar manner to results from human studies, a portion of the xylose intake is passed out in urine undigested.^[11]

Hydrogen production

In 2014 a low-temperature 50 °C (122 °F), atmospheric-pressure enzyme-driven process to convert xylose into hydrogen with nearly 100% of the theoretical yield was announced. The process employs 13 enzymes, including a novel polyphosphate xylulokinase (XK).^[12]^[13]

Derivatives

Reduction of xylose by catalytic hydrogenation produces the sugar substitute xylitol.

References

^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, ISBN 091191028X , 9995.
^ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-574. ISBN 0-8493-0462-8. .
^ Advances in carbohydrate chemistry, Volume 5, pg 278 Hudson & Cantor 1950
^ Pentose Metabolism 1932
^ Buskas, Therese; Ingale, Sampat; Boons, Geert-Jan (2006), "Glycopeptides as versatile tool for glycobiology", Glycobiology 16 (8): 113R–36R, doi:10.1093/glycob/cwj125, PMID 16675547
^ Roger Adams and V. Voorhees (1921). "Furfural". Org. Synth. 1: 49. ; Coll. Vol. 1, p. 280
^ H. E. Hoydonckx, W. M. Van Rhijn, W. Van Rhijn, D. E. De Vos, P. A. Jacobs "Furfural and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2007, Wiley-VCH, Weinheim. doi:10.1002/14356007.a12_119.pub2
^ Johnson, S. A. (2006). "Thesis" (PDF).
^ GASTRO-INTESTINAL STUDIES. VII. THE EXCRETION OF XYLOSE IN PERNICIOUS ANEMIA, The Journal of Clinical Investigation, retrieved 2016-02-17
^ "D-xylose absorption", MedlinePlus (U.S. National Library of Medicine), July 2008, retrieved 2009-09-06
^ Nutritional implications of D-Xylose in pigs
^ "Virginia Tech team develops process for high-yield production of hydrogen from xylose under mild conditions". Green Car Congress. 2013-04-03. doi:10.1002/anie.201300766. Retrieved 2014-01-22.
^ Martín Del Campo, J. S.; Rollin, J.; Myung, S.; Chun, Y.; Chandrayan, S.; Patiño, R.; Adams, M. W.; Zhang, Y. -H. P. (2013). "High-Yield Production of Dihydrogen from Xylose by Using a Synthetic Enzyme Cascade in a Cell-Free System". Angewandte Chemie International Edition 52 (17): 4587. doi:10.1002/anie.201300766.

UpToDate Contents

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1. 吸収不良の臨床的特徴および診断 clinical features and diagnosis of malabsorption
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5. ロタウイルス感染の臨床症状および診断 clinical manifestations and diagnosis of rotavirus infection

English Journal

Microwave-assisted acid hydrolysis to produce xylooligosaccharides from sugarcane bagasse hemicelluloses.

Bian J1, Peng P2, Peng F1, Xiao X1, Xu F1, Sun RC3.Author information 1Beijing Key Laboratory of Lignocellulosic Chemistry, College of Materials Science and Technology, Beijing Forestry University, Beijing 100083, China.2College of Forestry, Northwest A&F University, Yangling 712100, China.3Beijing Key Laboratory of Lignocellulosic Chemistry, College of Materials Science and Technology, Beijing Forestry University, Beijing 100083, China; State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou 510640, China. Electronic address: rcsun3@bjfu.edu.cn.AbstractHemicelluloses from sugarcane bagasse were subjected to microwave-assisted acid hydrolysis at mild temperature to produce xylooligosaccharides (XOS). The hydrolysis was performed with dilute H2SO4 at 90°C and the influence of acid concentration (0.1-0.3M) and reaction time (20-40min) on the XOS production was ascertained with response surface methodology based on central composite design. The fitted models of XOS and xylose yields were in good agreement with the experimental results. Compared to hydrolysis time, acid concentration was a more significant coefficient in the production of XOS. A well-defined degree of polymerisation of XOS and the monomer in the hydrolysates were quantified. No sugar-degraded byproduct was detected. The maximum XOS yield of 290.2mgg(-1) was achieved by hydrolysis with 0.24M H2SO4 for 31min. The results indicated that the yields of xylose and the byproducts can be controlled by the acid concentration and reaction time in microwave-assisted acid hydrolysis.
Food chemistry.Food Chem.2014 Aug 1;156:7-13. doi: 10.1016/j.foodchem.2014.01.112. Epub 2014 Feb 6.
Hemicelluloses from sugarcane bagasse were subjected to microwave-assisted acid hydrolysis at mild temperature to produce xylooligosaccharides (XOS). The hydrolysis was performed with dilute H2SO4 at 90°C and the influence of acid concentration (0.1-0.3M) and reaction time (20-40min) on the XOS pro
PMID 24629931

Identification and origin of odorous sulfur compounds in cooked ham.

Thomas C1, Mercier F2, Tournayre P2, Martin JL3, Berdagué JL2.Author information 1IFIP - Laboratoire d'Essais et de Mesures Physiques, 94704 Maisons-Alfort, France. Electronic address: caroline.thomas@clermont.inra.fr.2Institut National de la Recherche Agronomique (INRA), UR 370 QuaPA, MASS group, 63122 Saint-Genès-Champanelle, France.3IFIP - Laboratoire d'Essais et de Mesures Physiques, 94704 Maisons-Alfort, France.AbstractThe aim of this work was to identify and gain further knowledge on the origin of sulfur compounds present in the volatile fraction of cooked ham, and on their role in the aroma of this product. To this end, we performed analyses by one- and two-dimensional gas chromatography coupled with mass spectrometry, and olfactometry. Among the odorant sulfur compounds identified, three furans present in trace amounts proved to have very intense odours responsible for the "meaty, cooked ham" notes of this pork product. They were 2-methyl-3-furanthiol, 2-methyl-3-(methyldithio)furan and bis(2-methyl-3-furyl) disulphide. Addition of thiamine or cysteine also enabled us to study the effect of these odour precursors on the formation of odorant furans during the cooking of ham. The results revealed a direct link between the thermal degradation of thiamine and the formation of these compounds. By contrast, addition of cysteine in the presence of fructose or xylose did not appreciably increase their production.
Food chemistry.Food Chem.2014 Jul 15;155:207-13. doi: 10.1016/j.foodchem.2014.01.029. Epub 2014 Jan 23.
The aim of this work was to identify and gain further knowledge on the origin of sulfur compounds present in the volatile fraction of cooked ham, and on their role in the aroma of this product. To this end, we performed analyses by one- and two-dimensional gas chromatography coupled with mass spectr
PMID 24594176

Establishment of the purity values of carbohydrate certified reference materials using quantitative nuclear magnetic resonance and mass balance approach.

Quan C.Author information Division of Chemistry, National Institute of Metrology, Beijing 100013, China. Electronic address: superfluidcan@hotmail.com.AbstractThis work described the assignment of purity values to six carbohydrate certified reference materials, including glucose, fructose, galactose, lactose, xylose and sucrose, according to the ISO Guides 34 and 35. The CRMs' purity values were assigned based on the weighted average of quantitative nuclear magnetic resonance method and mass balance approach with high resolution liquid chromatography - evaporative light scattering detection. All the six CRMs with following value amount fractions: glucose (GBW10062) at a certified purity P ± U (k=2) of (0.99 ± 0.005)%; fructose (GBW10063) at (0.99 ± 0.005)%; galactose (GBW10064) at (0.99 ± 0.007)%; lactose (GBW10065) at (0.99 ± 0.008)%; xylose (GBW10066) at (0.99 ± 0.007)% and sucrose (GBW10067) at (0.99 ± 0.008)%, respectively were certified. The homogeneity of the CRMs was determined by an in-house validated liquid chromatographic method. Potential degradation during storage was also investigated and a shelf-life based on this value was established.
Food chemistry.Food Chem.2014 Jun 15;153:378-86. doi: 10.1016/j.foodchem.2013.12.086. Epub 2014 Jan 3.
This work described the assignment of purity values to six carbohydrate certified reference materials, including glucose, fructose, galactose, lactose, xylose and sucrose, according to the ISO Guides 34 and 35. The CRMs' purity values were assigned based on the weighted average of quantitative nucle
PMID 24491743

Japanese Journal

Boost in bioethanol production using recombinant Saccharomyces cerevisiae with mutated strictly NADPH-dependent xylose reductase and NADP(+)-dependent xylitol dehydrogenase.

Khattab Sadat Mohammad Rezq,Saimura Masayuki,Kodaki Tsutomu
Journal of biotechnology 165(3-4), 153-156, 2013-06-10
… The xylose-fermenting recombinant Saccharomyces cerevisiae and its improvement have been studied extensively. … The redox balance between xylose reductase (XR) and xylitol dehydrogenase (XDH) is thought to be an important factor in effective xylose fermentation. …
NAID 120005245131

A wild and tolerant yeast suitable for ethanol fermentation from lignocellulose(ENVIRONMENTAL BIOTECHNOLOGY)

Kodama Shotaro,Nakanishi Hiroshi,Thalagala Thalagala Arachchige Tharanga Piyamali,Isono Naoto,Hisamatsu Makoto
Journal of bioscience and bioengineering 115(5), 557-561, 2013-05-00
… Therefore, we first isolated acid- and salt-tolerant yeast that are capable of fermenting various monosaccharides to ethanol, and the isolated yeast that showed the ability to ferment ethanol from glucose, mannose, galactose, fructose, and xylose, was identified as Zygoascus hellenicus LK-5G on the basis of the 26S rRNA sequence analysis. …
NAID 110009611463

Construction of a Candida utilis strain with ratio-optimized expression of xylose-metabolizing enzyme genes by cocktail multicopy integration method(MICROBIAL PHYSIOLOGY AND BIOTECHNOLOGY)

Tamakawa Hideyuki,Ikushima Shigehito,Yoshida Satoshi
Journal of bioscience and bioengineering 115(5), 532-539, 2013-05-00
… We previously reported the construction of a recombinant Candida utilis strain expressing mXYL1, XYL2 and XYL3, which encode mutated Candida shehatae xylose reductase K275R/N277D, C. … shehatae xylitol dehydrogenase and Pichia stipitis xylulokinase to produce ethanol from xylose. … In this study, to breed a strain with higher productivity of ethanol from xylose, we used a cocktail multicopy integration method to attain optimized gene dosage of the three enzymes. …
NAID 110009611458

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★リンクテーブル★

リンク元	「キシロース」
拡張検索	「D-xylose」

「キシロース」

D-Xylose
Names
	IUPAC name D-Xylose
	Other names (+)-Xylose; Wood sugar
Identifiers
CAS Number	58-86-6 ; 609-06-3 (L-isomer) [ESIS]; 41247-05-6 (racemate) [ESIS]
ChEMBL	ChEMBL502135
ChemSpider	119104
EC Number	200-400-7
Jmol interactive 3D	Image
PubChem	135191
UNII	A1TA934AKO
	InChI InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1 Key: SRBFZHDQGSBBOR-IOVATXLUSA-N ; InChI=1/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1 Key: SRBFZHDQGSBBOR-IOVATXLUBL ;
	SMILES C1[C@H]([C@@H]([C@H](C(O1)O)O)O)O ;
Properties
Chemical formula	C5H10O5
Molar mass	150.13 g/mol
Appearance	monoclinic needles or prisms, colourless
Density	1.525 g/cm3 (20 °C)
Melting point	144 to 145 °C (291 to 293 °F; 417 to 418 K)
Chiral rotation ([α]D)	+22.5° (CHCl3)
Hazards
NFPA 704	1 1 0
Related compounds
Related aldopentoses	Arabinose; Ribose; Lyxose
Related compounds	Xylulose
	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

　　[★]

英: xylose Xyl
関: D-キシロース吸収試験、キシリトール

アルドペントースの一種、植物由来アルド五炭糖、低カロリー甘味料

参考

wiki ja

http://ja.wikipedia.org/wiki/%E3%82%AD%E3%82%B7%E3%83%AD%E3%83%BC%E3%82%B9

「D-xylose」

　　[★]

D-キシロース

関: xylose

同: Xylo-phan

[1] The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, ISBN 091191028X , 9995.

[2] Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-574. ISBN 0-8493-0462-8. .

[3] Advances in carbohydrate chemistry, Volume 5, pg 278 Hudson & Cantor 1950

[4] Pentose Metabolism 1932

[5] Buskas, Therese; Ingale, Sampat; Boons, Geert-Jan (2006), "Glycopeptides as versatile tool for glycobiology", Glycobiology 16 (8): 113R–36R, doi:10.1093/glycob/cwj125, PMID 16675547

[6] Roger Adams and V. Voorhees (1921). "Furfural". Org. Synth. 1: 49. ; Coll. Vol. 1, p. 280

[7] H. E. Hoydonckx, W. M. Van Rhijn, W. Van Rhijn, D. E. De Vos, P. A. Jacobs "Furfural and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2007, Wiley-VCH, Weinheim. doi:10.1002/14356007.a12_119.pub2

[8] Johnson, S. A. (2006). "Thesis" (PDF).

[9] GASTRO-INTESTINAL STUDIES. VII. THE EXCRETION OF XYLOSE IN PERNICIOUS ANEMIA, The Journal of Clinical Investigation, retrieved 2016-02-17

[10] "D-xylose absorption", MedlinePlus (U.S. National Library of Medicine), July 2008, retrieved 2009-09-06

[11] Nutritional implications of D-Xylose in pigs

[12] "Virginia Tech team develops process for high-yield production of hydrogen from xylose under mild conditions". Green Car Congress. 2013-04-03. doi:10.1002/anie.201300766. Retrieved 2014-01-22.

[13] Martín Del Campo, J. S.; Rollin, J.; Myung, S.; Chun, Y.; Chandrayan, S.; Patiño, R.; Adams, M. W.; Zhang, Y. -H. P. (2013). "High-Yield Production of Dihydrogen from Xylose by Using a Synthetic Enzyme Cascade in a Cell-Free System". Angewandte Chemie International Edition 52 (17): 4587. doi:10.1002/anie.201300766.

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案内

xylose