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Laxatives
L-Glucose
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L-Glucose

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l-Glucose
L-Glucose structure.svg
Haworth projection of α-L-Glucopyranose.svg
Haworth projection of α-l-glucopyranose
Names
IUPAC name
l-Glucose
Identifiers
3D model (JSmol)
Abbreviations L-Glc
ChEBI
ChemSpider
EC Number
  • 213-068-3
PubChem CID
UNII
  • InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6?/m0/s1 checkY
    Key: WQZGKKKJIJFFOK-ZZWDRFIYSA-N checkY
  • InChI=1/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6?/m0/s1
    Key: WQZGKKKJIJFFOK-ZZWDRFIYBQ
  • O[C@@H]1[C@@H](O)[C@@H](OC(O)[C@H]1O)CO
Properties
C6H12O6
Molar mass 180.156 g·mol−1
Density 1.54 g/cm3
91 g/100 mL
Hazards
Safety data sheet (SDS) ICSC 0865
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 ?)

l-Glucose is an organic compound with formula C6H12O6 or O=CH[CH(OH)]5H, specifically one of the aldohexose monosaccharides. As the l-isomer of glucose, it is the enantiomer of the more common d-glucose.

l-Glucose does not occur naturally in living organisms, but can be synthesized in the laboratory. l-Glucose is indistinguishable in taste from d-glucose, but cannot be used by living organisms as a source of energy because it cannot be phosphorylated by hexokinase, the first enzyme in the glycolysis pathway. One of the known exceptions is in Burkholderia caryophylli, a plant pathogenic bacterium, which contains the enzyme d-threo-aldose 1-dehydrogenase which is capable of oxidizing l-glucose.

Like the d-isomer, l-glucose usually occurs as one of four cyclic structural isomers—α- and β-l-glucopyranose (the most common, with a six-atom ring), and α- and β-l-glucofuranose (with a five-atom ring). In water solution, these isomers interconvert in matters of hours, with the open-chain form as an intermediate stage.

Uses

l-Glucose was once proposed as a low-calorie sweetener and it is suitable for patients with diabetes mellitus, but it was never marketed due to excessive manufacturing costs.

The acetate derivative of l-glucose, l-glucose pentaacetate, was found to stimulate insulin release, and might therefore be of therapeutic value for type 2 diabetes.l-Glucose was also found to be a laxative, and has been proposed as a colon-cleansing agent which would not produce the disruption of fluid and electrolyte levels associated with the significant liquid quantities of bad-tasting osmotic laxatives conventionally used in preparation for colonoscopy.

External links

  • Media related to L-Glucose at Wikimedia Commons

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