Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-05-15 05:08:47 UTC
Update Date2025-10-07 16:06:13 UTC
Metabolite IDMMDBc0013980
Metabolite Identification
Common NameLysodektose
DescriptionLysodektose is a trisaccharide belonging to the chemical class of hydroxylamine derivatives. It is characterized as 6-O-(2-deoxy-2-[N-methyl]hydroxylamino-beta-D-glucopyranosyl)-alpha-alpha-trehalose and has been isolated from the bacterium Micrococcus lysodeikticus. The compound has been purified through ion-exchange and gel-filtration chromatography, with its structure confirmed by mass spectroscopy, 2D NMR, and EPR techniques (PMID:2059316 ). Lysodektose undergoes oxidation in the presence of K3Fe(CN)6, leading to the formation of a nitroxyl radical and a nitrone, with the potential for reduction back to its original hydroxylamine form (PMID:2059316 ). Additionally, it can be specifically labeled with deuterium or tritium in the methyl group for further studies (PMID:2059316 ). In biological contexts, lysodektose can be transformed into an aminoxyl free radical upon oxidation, particularly in cells treated with vitamin K analogues (PMID:1648021 ). This transformation highlights its potential role in radical chemistry and its interactions within biological systems (PMID:2560374 ). Overall, lysodektose represents a significant metabolite with unique properties and biological implications.
Structure
Synonyms
ValueSource
6-O-(2-Deoxy-2-(N-methyl)hydroxylamino-beta-glucopyranosyl)alpha,alpha-trehaloseMeSH
Molecular FormulaC19H35NO16
Average Mass533.48
Monoisotopic Mass533.195584051
IUPAC Name2-({6-[({4,5-dihydroxy-3-[hydroxy(methyl)amino]-6-(hydroxymethyl)oxan-2-yl}oxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Name2-({6-[({4,5-dihydroxy-3-[hydroxy(methyl)amino]-6-(hydroxymethyl)oxan-2-yl}oxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol
CAS Registry NumberNot Available
SMILES
CN(O)C1C(O)C(O)C(CO)OC1OCC1OC(OC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O
InChI Identifier
InChI=1S/C19H35NO16/c1-20(31)8-12(26)9(23)5(2-21)33-17(8)32-4-7-11(25)14(28)16(30)19(35-7)36-18-15(29)13(27)10(24)6(3-22)34-18/h5-19,21-31H,2-4H2,1H3
InChI KeyLZVSAEWUJVJOLT-UHFFFAOYSA-N