Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:24:48 UTC
Update Date2024-04-30 19:30:51 UTC
Metabolite IDMMDBc0000014
Metabolite Identification
Common NameMelibiose
DescriptionMelibiose (CAS: 585-99-9) is a disaccharide consisting of one galactose and one glucose moiety in an alpha (1-6) glycosidic linkage. This sugar is produced and metabolized only by enteric and lactic acid bacteria and other microbes, such as Dickeya dadantii, Escherichia, Leuconostoc, and Saccharomyces (PMID: 19734309 , 28453942 ). It is not an endogenous metabolite but may be obtained from the consumption of partially fermented molasses, brown sugar, or honey. Antibodies to melibiose will appear in individuals affected by Chagas' disease (Trypanosoma cruzi infection). Melibiose is not metabolized by humans but can be broken down by gut microflora, such as E. coli. In fact, E. coli is able to utilize melibiose as a sole source of carbon. Melibiose is first imported by the melibiose permease, MelB and then converted into β-D-glucose and β-D-galactose by the α-galactosidase encoded by melA. Because of its poor digestibility, melibiose (along with rhamnose) can be used together for noninvasive intestinal mucosa barrier testing. This test can be used to assess malabsorption or impairment of intestinal permeability. Recent studies with dietary melibiose have shown that it can strongly affect the Th cell responses to an ingested antigen. It has been suggested that melibiose could be used to enhance the induction of oral tolerance (PMID: 17986780 ).
Structure
SynonymsNot Available
Molecular FormulaC12H22O11
Average Mass342.2965
Monoisotopic Mass342.116211546
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number13299-20-2
SMILESNot Available
InChI Identifier
InChI=1S/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5+,6-,7+,8+,9-,10-,11+,12+/m1/s1
InChI KeyDLRVVLDZNNYCBX-CQHUIXDMSA-N