Allolactose

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Allolactose
Skeletal formula of allolactose
Ball-and-stick model of the allolactose molecule
Names
IUPAC name
(3R,4S,5S,6R)-6-[[(2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol
Other names
6-O-β-D-Galactopyranosyl-D-glucose; β-D-Galactopyranosyl (1→6)-D-glucose
Identifiers
28447-39-4 N
ChEBI CHEBI:36229 YesY
ChemSpider 4957195 YesY
Jmol-3D images Image
PubChem 6454902
Properties
C12H22O11
Molar mass 342.296 g/mol
Density 1.768 g/mL
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Allolactose is a disaccharide similar to lactose. It consists of the monosaccharides D-galactose and D-glucose linked through a β1-6 glycosidic linkage instead of the β1-4 linkage of lactose. It may arise from the occasional transglycosylation of lactose by β-galactosidase.

It is an inducer of the lac operon in Escherichia coli. It binds to a subunit of the tetrameric lac repressor, which results in conformational changes and reduces the binding affinity of the lac repressor to the lac operator, thereby dissociating it from the lac operator. The absence of the repressor allows the transcription of the lac operon to proceed. A non-hydrolyzable analog of allolactose, isopropyl β-D-1-thiogalactopyranoside (IPTG), is normally used in molecular biology to induce the lac operon.

See also[edit]

External links[edit]