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Escherichia coli K-12 substr. MG1655 Compound: D-sorbitol

Synonyms: L-gulitol, D-glucitol, meglumine, iso-sorbide

Superclasses: all carbohydrates a carbohydrate a glycan a sugar a sugar alcohol a hexitol
an alcohol a sugar alcohol a hexitol

Component of: GutR-sorbitol (extended summary available)

Chemical Formula: C6H14O6

Molecular Weight: 182.17 Daltons

Monoisotopic Molecular Weight: 182.079038182 Daltons

D-sorbitol compound structure

SMILES: C(C(C(C(C(CO)O)O)O)O)O

InChI: InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1

InChIKey: InChIKey=FBPFZTCFMRRESA-JGWLITMVSA-N

Unification Links: CAS:50-70-4 , ChEBI:17924 , ChemSpider:5576 , DrugBank:DB01638 , HMDB:HMDB00247 , IAF1260:36018 , KEGG:C00794 , MetaboLights:MTBLC17924 , PubChem:5780

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -225.31

Reactions known to produce the compound:

Not in pathways:
a sugar phosphate + H2O → a sugar + phosphate

β-D-glucuronide and D-glucuronate degradation :
a β-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol

glycerophosphodiester degradation :
a glycerophosphodiester + H2O → an alcohol + sn-glycerol 3-phosphate + H+

Not in pathways:
an organic hydroperoxide + NADH + H+an alcohol + NAD+ + H2O
an N-acetyl-β-D-hexosaminide + H2O → an N-acetyl-β-D-hexosamine + an alcohol
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an acetic ester + H2O → an alcohol + acetate + H+
an organic hydroperoxide + a reduced thioredoxin → an alcohol + an oxidized thioredoxin + H2O
a phosphate monoester[periplasmic space] + H2O[periplasmic space]an alcohol[periplasmic space] + phosphate[periplasmic space]
a phosphate monoester[periplasmic space] + H2O[periplasmic space]an alcohol[periplasmic space] + phosphate[periplasmic space]

In Reactions of unknown directionality:

Not in pathways:
GutR + D-sorbitol = GutR-sorbitol

Not in pathways:
an alcohol + NADP+ = an aldehyde + NADPH + H+

In Transport reactions:
HPr-Phis15 + D-sorbitol[periplasmic space] → D-sorbitol 6-phosphate[cytosol] + HPr ,
a [PTS enzyme I]-Nπ-phospho-L-histidine + a sugar[periplasmic space] → a [PTS enzyme I]-L-histidine + a sugar phosphate[cytosol]

Enzymes inhibited by D-sorbitol, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: D-mannonate dehydratase [RobertBaudouy73]

Inhibitor (Mechanism unknown) of: transport and phosphorylation of D-mannitol [Jacobson83]

This compound has been characterized as an alternative substrate of the following enzymes: diffusion of glycerol

In Growth Media: PMA carbon source test + D-sorbitol


References

Jacobson83: Jacobson GR, Tanney LE, Kelly DM, Palman KB, Corn SB (1983). "Substrate and phospholipid specificity of the purified mannitol permease of Escherichia coli." J Cell Biochem 23(1-4);231-40. PMID: 6427236

RobertBaudouy73: Robert-Baudouy JM, Stoeber FR (1973). "[Purification and properties of D-mannonate hydrolyase from Escherichia coli K12]." Biochim Biophys Acta 1973;309(2);473-85. PMID: 4581499


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 19.0 on Fri Aug 28, 2015, biocyc11.