Xylose

Source: Wikipedia, the free encyclopedia.
"Wood sugar" redirects here. For the related sugar alcohol, see Xylitol.
d-Xylose
D-Xylopyranose
D-Xylopyranose
Xylofuranose
Xylofuranose
Xylose chair
Xylose linear
Names
IUPAC name
d-Xylose
Other names
(+)-Xylose
Wood sugar
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
ECHA InfoCard
 100.043.072 Edit this at Wikidata
EC Number
  • 200-400-7
UNII
  • InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1 ☒N
    Key: SRBFZHDQGSBBOR-IOVATXLUSA-N ☒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
  • C1[C@H]([C@@H]([C@H](C(O1)O)O)O)O
Properties[1][2]
C
5H
10O
5
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)
+22.5° (CHCl
3)
-84.80·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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).
☒N verify (what is checkY☒N ?)

Xylose (cf.

aldehyde group, it is a reducing sugar
.

Structure

The

acyclic form of xylose has chemical formula HOCH
2(CH(OH))3CHO. The cyclic hemiacetal isomers are more prevalent in solution and are of two types: the pyranoses, which feature six-membered C
5O rings, and the furanoses
, which feature five-membered C
4O rings (with a pendant CH
2OH group). Each of these rings is subject to further isomerism, depending on the relative orientation of the anomeric hydroxy group.

The

dextrorotary form, d-xylose, is the one that usually occurs endogenously in living things. A levorotary form, l-xylose, can be synthesized
.

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

anionic polysaccharides such as heparan sulfate and chondroitin sulfate.[5]

Xylose is also found in some species of Chrysolinina beetles, including Chrysolina coerulans. They have

cardiac glycosides (including xylose) in their defensive glands.[6]

Applications

Chemicals

The acid-catalysed degradation of hemicellulose gives furfural,[7][8] a precursor to synthetic polymers and to tetrahydrofuran.[9]

Human consumption

Xylose is metabolised by humans, although it is not a major human nutrient and is largely excreted by the kidneys.

eukaryotic microorganisms. Humans have enzymes called protein xylosyltransferases (XYLT1, XYLT2
) which transfer xylose from UDP to a serine in the core protein of proteoglycans.

Xylose contains 2.4 calories per gram[11] (lower than glucose or sucrose, approx. 4 calories per gram).

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.[12]

High xylose intake on the order of approximately 100 g/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.[13]

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).[14][15]

Derivatives

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

See also

References

  1. ISBN 091191028X
    , 9995.
  2. ISBN 0-8493-0462-8
    ..
  3. ISBN 9780080562643
    .
  4. doi:10.1016/S0021-9258(18)76145-0
    .
  5. PMID 16675547
  6. ISBN 9780854046911
    .
  7. doi:10.15227/orgsyn.001.0049
    ; Collected Volumes, vol. 1, p. 280.
  8. S2CID 104358224
    .
  9. ISBN 978-3527306732
    .
  10. hdl:2263/27501
    .
  11. ^ US US6239274B1, "Method of producing xylose", issued 1999-08-06 
  12. ^ "D-xylose absorption", MedlinePlus, U.S. National Library of Medicine, July 2008, retrieved 2009-09-06
  13. S2CID 27670020
    .
  14. S2CID 1915746
    . Retrieved 2014-01-22.
  15. S2CID 1915746
    .
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