Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-04-29 22:47:30 UTC
Update Date2025-10-07 16:08:15 UTC
Metabolite IDMMDBc0049979
Metabolite Identification
Common NameLevanbiose
DescriptionLevanbiose is a fructooligosaccharide belonging to the chemical class of oligosaccharides. Its chemical structure consists of a linear chain of fructose units linked by β(2→6) glycosidic bonds, with a terminal glucose unit, which distinguishes it from other fructans. In biochemical pathways, levanbiose is produced through the action of fructanases, particularly in certain bacterial strains, and is involved in the metabolism of carbohydrates. It has been shown to accumulate differentially in various cultivars, indicating its role in plant metabolism (PMID:38001769 ). Additionally, levanbiose is implicated in the modulation of sperm motility, as it has been found to be negatively correlated with total progressive motile sperm count (TPMSC) in bulls, suggesting its potential impact on reproductive biology (PMID:39887007 ). The structure of levanbiose has been studied in complex with levansucrase, revealing insights into its binding interactions and enzymatic processes (PMID:31877648 ). Overall, levanbiose serves as a significant metabolite in both microbial and reproductive contexts, reflecting its diverse roles in biological systems.
Structure
Synonyms
ValueSource
O-beta-D-Fructofuranosyl-(2-6)beta-D-fructofuranosideMeSH
Molecular FormulaC12H22O11
Average Mass342.2965
Monoisotopic Mass342.116211546
IUPAC Name(2R,3S,4S,5R)-5-({[(2R,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-2-(hydroxymethyl)oxolane-2,3,4-triol
Traditional Namelevanbiose
CAS Registry NumberNot Available
SMILES
[H][C@@]1(O)[C@@]([H])(CO[C@]2(CO)O[C@]([H])(CO)[C@@]([H])(O)[C@]2([H])O)O[C@](O)(CO)[C@@]1([H])O
InChI Identifier
InChI=1S/C12H22O11/c13-1-5-7(16)10(19)12(4-15,23-5)21-2-6-8(17)9(18)11(20,3-14)22-6/h5-10,13-20H,1-4H2/t5-,6-,7-,8-,9+,10+,11-,12-/m1/s1
InChI KeyFEXBYMWJVRXRSN-TWOHWVPZSA-N