L-Glucose

{{DISPLAYTITLE:L-Glucose}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477496828

| Name = {{sm|l}}-Glucose

| ImageFile = L-Glucose structure.svg

| ImageClass = skin-invert-image

| ImageSize = 150 px

| ImageFile2 = Haworth projection of α-L-Glucopyranose.svg

| ImageClass2 = skin-invert-image

| ImageFile3 = L-Glucose Fischer Projection.svg

| ImageClass3 = skin-invert-image

| ImageSize2 = 135 px

| ImageCaption2 = Haworth projection of α-{{sm|l}}-glucopyranose

| ImageCaption3 = Fischer projection of {{sm|l}}-glucose

| IUPACName = {{sm|l}}-Glucose

| Section1 = {{Chembox Identifiers

| Abbreviations = L-Glc

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 921-60-8

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 02833ISA66

| EINECS = 213-068-3

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 37627

| PubChem = 2724488

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2006622

| SMILES = O[C@@H]1[C@@H](O)[C@@H](OC(O)[C@H]1O)CO

| 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

| InChIKey = WQZGKKKJIJFFOK-ZZWDRFIYBQ

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = WQZGKKKJIJFFOK-ZZWDRFIYSA-N

}}

| Section2 = {{Chembox Properties

| C=6 | H=12 | O=6

| Density = 1.54 g/cm³

| Solubility = 91 g/100 mL

}}

| Section7 = {{Chembox Hazards

| ExternalSDS = [http://www.inchem.org/documents/icsc/icsc/eics0865.htm ICSC 0865]

}}

}}

{{sm|l}}-Glucose is an organic compound with formula C₆H₁₂O₆ or O=CH[CH(OH)]₅H, specifically one of the aldohexose monosaccharides. As the Monosaccharide#Configuration of monosaccharides of glucose, it is the enantiomer of the more common glucose.

{{sm|l}}-Glucose does not occur naturally in living organisms, but can be synthesized in the laboratory. {{sm|l}}-Glucose is indistinguishable in taste from {{sm|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 Trinickia caryophylli, a plant pathogenic bacterium, which contains the enzyme D-threo-aldose 1-dehydrogenase which is capable of oxidizing {{sm|l}}-glucose.{{Cite journal | last1 = Sasajima | first1 = K. | last2 = Sinskey | first2 = A. | doi = 10.1016/0005-2744(79)90232-8 | title = Oxidation of l-glucose by a Pseudomonad | journal = Biochimica et Biophysica Acta (BBA) - Enzymology | volume = 571 | pages = 120–126 | year = 1979 | issue = 1 | pmid = 40609}}

Like the {{sm|d}}-isomer, {{sm|l}}-glucose usually occurs as one of four cyclic structural isomers—α- and β-{{sm|l}}-glucopyranose (the most common, with a six-atom ring), and α- and β-{{sm|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.