Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-05 23:13:58 UTC
Update Date2025-10-07 16:08:32 UTC
Metabolite IDMMDBc0054466
Metabolite Identification
Common NamedTDP-4-amino-4,6-dideoxy-alpha-D-glucose
DescriptiondTDP-4-amino-4,6-dideoxy-alpha-D-glucose is a nucleotide sugar belonging to the class of deoxynucleotides. It features a unique structure characterized by an amino group at the 4-position and the absence of hydroxyl groups at the 4 and 6 positions of the glucose moiety, which classifies it as a dideoxy sugar. The compound plays a crucial role in various biosynthetic pathways, particularly in the synthesis of glycoproteins and polysaccharides. Notably, it is a precursor in the biosynthesis of the alpha-glucosidase inhibitor acarbose, where it is synthesized from galactose through a complex series of reactions involving 16 steps (PMID:11841810 ). The synthesis process includes the removal of benzyl protecting groups, reduction of an azide, and subsequent coupling with an activated nucleoside phosphate to yield dTDP-4-amino-4,6-dideoxy-alpha-D-glucose (PMID:11841810 ). This metabolite exemplifies the intricate biochemical pathways that contribute to the formation of carbohydrate structures critical for various biological functions.
Structure
Synonyms
ValueSource
dTDP-4-Amino-4,6-dideoxy-alpha-D-glucopyranoseChEBI
dTDP-4-Amino-4,6-dideoxy-D-glucoseChEBI
dTDP-ViosamineKegg
dTDP-4-Amino-4,6-dideoxy-a-D-glucopyranoseGenerator
dTDP-4-Amino-4,6-dideoxy-α-D-glucopyranoseGenerator
dTDP-4-Amino-4,6-dideoxy-a-D-glucoseGenerator
dTDP-4-Amino-4,6-dideoxy-α-D-glucoseGenerator
dTDP-4-a-DDGMeSH
dTDP-4-amino-4,6-Dideoxy-glucoseMeSH
Molecular FormulaC16H27N3O14P2
Average Mass547.3448
Monoisotopic Mass547.096825611
IUPAC Name[({[(2R,3R,4S,5S,6R)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid
Traditional Name{[(2R,3R,4S,5S,6R)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy(hydroxy)phosphoryl}oxy[(2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@]1(O)C[C@@]([H])(O[C@]1([H])COP(O)(=O)OP(O)(=O)O[C@@]1([H])O[C@]([H])(C)[C@@]([H])(N)[C@]([H])(O)[C@@]1([H])O)N1C=C(C)C(O)=NC1=O
InChI Identifier
InChI=1S/C16H27N3O14P2/c1-6-4-19(16(24)18-14(6)23)10-3-8(20)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(17)7(2)30-15/h4,7-13,15,20-22H,3,5,17H2,1-2H3,(H,25,26)(H,27,28)(H,18,23,24)/t7-,8+,9-,10-,11-,12+,13-,15-/m1/s1
InChI KeyUIVJXHWSIFBBCY-LPGAPTBISA-N