Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-05-15 18:30:16 UTC
Update Date2025-10-07 16:07:51 UTC
Metabolite IDMMDBc0028735
Metabolite Identification
Common NameKanosamine
DescriptionKanosamine is a carbohydrate derivative belonging to the class of amino sugars. Chemically, it is synthesized from glucose 6-phosphate (G6P) in Bacillus subtilis through a series of enzymatic reactions involving NtdC, which catalyzes the NAD-dependent oxidation of the C3-hydroxyl group, NtdA, a pyridoxal phosphate-dependent aminotransferase, and NtdB, a phosphatase. This biosynthetic pathway yields kanosamine 6-phosphonate analogues from 3-keto products, highlighting its structural complexity, including a sugar ring that replaces garosamine in gentamicin derivatives (PMID:40342992 ). The C1 and C6O positions of kanosamine are modified by a cytosine base and a 3-amino-3-deoxyglucose moiety, respectively (PMID:34569228 ). Kanosamine is implicated in the production of antimicrobial compounds, as evidenced by gene clusters identified in the complete genome sequence of Bacillus subtilis AMFE023/7 (PMID:40718143 ). Additionally, it plays a role in the ASA pathway, with intermediates such as kanosamine, AHAB, and ASA being relevant for overproduction strategies (PMID:34374768 ). The biosynthesis of kanosamine also demonstrates substrate substitution capabilities, as shown by phosphonates and phosphite rescue experiments (PMID:34096710 ).
Structure
SynonymsNot Available
Molecular FormulaC6H13NO5
Average Mass179.172
Monoisotopic Mass179.079372523
IUPAC Name4-amino-6-(hydroxymethyl)oxane-2,3,5-triol
Traditional Name4-amino-6-(hydroxymethyl)oxane-2,3,5-triol
CAS Registry NumberNot Available
SMILES
NC1C(O)C(O)OC(CO)C1O
InChI Identifier
InChI=1S/C6H13NO5/c7-3-4(9)2(1-8)12-6(11)5(3)10/h2-6,8-11H,1,7H2
InChI KeyBQCCAEOLPYCBAE-UHFFFAOYSA-N