Structure via PubChem · Public domain (PubChem)
melibiose
Sign in to saveMelibiose is a reducing disaccharide formed by an α-1,6 linkage between galactose and glucose (D-Gal-(α1→6)-D-Glc). It differs from lactose in the chirality of the carbon where the galactose ring is closed and that the galactose is linked to a different point on the glucose moiety. It can be formed by invertase-mediated hydrolysis of raffinose, which produces melibiose and fructose. Melibiose can be broken down into its component saccharides, glucose and galactose, by the enzyme alpha-galactosidase, such as MEL1 from Saccharomyces pastorianus (lager yeast).
In the Vinony graph
Within Vinony's link graph, melibiose is referenced by 40 other articles, and connects out to International Standard Book Number, glucose and chemical formula.
It sits within the topics Chembox image size set, Disaccharides and ECHA InfoCard ID from Wikidata.
Its subject is documented across 14 Wikipedia language editions.
Chemical data
- Formula
- C12H22O11
- Molecular weight
- 342.3 g/mol
- IUPAC name
- (3R,4S,5S,6R)-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol
- SMILES
- C([C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H](C(O2)O)O)O)O)O)O)O)O
- InChIKey
- DLRVVLDZNNYCBX-ABXHMFFYSA-N
- XLogP
- -4.7
- Polar surface area
- 190 Ų
- H-bond donors
- 8
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,291 papers- The melibiose carrier of Escherichia coli.Research in microbiology · 1990
- The melibiose-derived glycation product mimics a unique epitope present in human and animal tissues.Scientific reports · 2021
- The melibiose/Na+ symporter of Escherichia coli: kinetic and molecular properties.Philosophical transactions of the Royal Society of London. Series B, Biological sciences · 1990
- Indium-mediated C-allylation of melibiose.Beilstein journal of organic chemistry · 2019
- Substrate-binding guides individual melibiose permeases MelB to structurally soften and to destabilize cytoplasmic middle-loop C3.Structure (London, England : 1993) · 2023
via PubMed
Wikidata facts
- Part of
- royal jelly
- Has part
- hydrogen
- Mass
- 342.116211524
Show 5 more facts
- isomeric SMILES
- OC[C@H]1O[C@H](OC[C@H]2OC(O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1O
- chemical formula
- C₁₂H₂₂O₁₁
- canonical SMILES
- OCC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1O
- found in taxon
- Escherichia coli
- Commons category
- Melibiose
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Melibiose is a reducing disaccharide formed by an α-1,6 linkage between galactose and glucose (D-Gal-(α1→6)-D-Glc). It differs from lactose in the chirality of the carbon where the galactose ring is closed and that the galactose is linked to a different point on the glucose moiety. It can be formed by invertase-mediated hydrolysis of raffinose, which produces melibiose and fructose. Melibiose can be broken down into its component saccharides, glucose and galactose, by the enzyme alpha-galactosidase, such as MEL1 from Saccharomyces pastorianus (lager yeast).
Melibiose cannot be used by Saccharomyces cerevisiae (ale yeast), so this is one test to differentiate between the two yeast species.
Excerpted from Wikipedia’s “melibiose” article, available under the CC BY-SA 4.0 licence.