Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-05-16 21:17:26 UTC
Update Date2025-10-07 16:08:18 UTC
Metabolite IDMMDBc0053209
Metabolite Identification
Common NamedTDP-L-dihydrostreptose
DescriptiondTDP-L-dihydrostreptose is a nucleotide sugar belonging to the class of glycosyl donors, specifically a derivative of dTDP (deoxythymidine diphosphate). Its chemical structure features a deoxythymidine moiety linked to a L-dihydrostreptose sugar, which plays a crucial role in various biosynthetic pathways. Notably, dTDP-L-dihydrostreptose serves as a substrate for the enzyme dihydrostreptosyltransferase, which catalyzes the transfer of L-dihydrostreptose to streptidine-6-phosphate, a key step in the biosynthesis of the antibiotic streptomycin (PMID:6157663 , PMID:6768553 ). The purification of this enzyme from Streptomyces griseus has been achieved through a multi-step chromatography process (PMID:6768553 ). Additionally, two distinct enzymes in Streptomyces griseus are involved in the synthesis of dTDP-L-dihydrostreptose from dTDP-6-deoxy-D-xylo-4-hexosulose, highlighting its importance in the metabolic pathways leading to antibiotic production (PMID:238519 ). Overall, dTDP-L-dihydrostreptose is integral to the biosynthetic machinery of certain actinomycetes, facilitating the formation of clinically relevant compounds.
Structure
SynonymsNot Available
Molecular FormulaC16H26N2O15P2
Average Mass548.331
Monoisotopic Mass548.080842141
IUPAC Name{[(2R,3R,4S,5S)-3,4-dihydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy}({[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphinic acid
Traditional Name[(2R,3R,4S,5S)-3,4-dihydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy([hydroxy([(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3H-pyrimidin-1-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
C[C@@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H](C[C@@H]2O)N2C=C(C)C(=O)NC2=O)[C@H](O)[C@@]1(O)CO
InChI Identifier
InChI=1S/C16H26N2O15P2/c1-7-4-18(15(23)17-13(7)22)11-3-9(20)10(31-11)5-29-34(25,26)33-35(27,28)32-14-12(21)16(24,6-19)8(2)30-14/h4,8-12,14,19-21,24H,3,5-6H2,1-2H3,(H,25,26)(H,27,28)(H,17,22,23)/t8-,9-,10+,11+,12-,14+,16+/m0/s1
InChI KeyLOULRGSWJAXPFN-JHJMUWKLSA-N