Thymidine diphosphate glucose
Names
IUPAC name
Thymidine 5′-(α-D -glucopyranosyl trihydrogen diphosphate)
Systematic IUPAC name
O 1 -{[(2R ,3S ,5R )-3-Hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(3H )-yl)oxolan-2-yl]methyl} O 3 -[(2R ,3R ,4S ,5S ,6R )-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] dihydrogen diphosphate
Other names
TDP-glucose; dTDP-glucose
Identifiers
ChEBI
ChEMBL
ChemSpider
InChI=1S/C16H26N2O16P2/c1-6-3-18(16(25)17-14(6)24)10-2-7(20)9(31-10)5-30-35(26,27)34-36(28,29)33-15-13(23)12(22)11(21)8(4-19)32-15/h3,7-13,15,19-23H,2,4-5H2,1H3,(H,26,27)(H,28,29)(H,17,24,25)/t7-,8+,9+,10+,11+,12-,13+,15+/m0/s1
Y Key: YSYKRGRSMLTJNL-URARBOGNSA-N
Y
CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)COP(=O)(O)OP(=O)(O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
O=C1\C(=C/N(C(=O)N1)[C@@H]2O[C@@H]([C@@H](O)C2)COP(=O)(O)OP(=O)(O)O[C@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)CO)C
Properties
C 16 H 26 N 2 O 16 P 2
Molar mass
−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Thymidine diphosphate glucose (often abbreviated dTDP-glucose or TDP-glucose ) is a nucleotide-linked sugar consisting of deoxythymidine diphosphate linked to glucose . It is the starting compound for the syntheses of many deoxysugars .[ 1]
Biosynthesis
DTDP-glucose is produced by the enzyme glucose-1-phosphate thymidylyltransferase and is synthesized from dTTP and glucose-1-phosphate . Pyrophosphate is a byproduct of the reaction.
Uses within the cell
DTDP-glucose goes on to form a variety of compounds in nucleotide sugars metabolism . Many bacteria utilize dTDP-glucose to form exotic sugars that are incorporated into their lipopolysaccharides or into secondary metabolites such as antibiotics . During the syntheses of many of these exotic sugars, dTDP-glucose undergoes a combined oxidation/reduction reaction via the enzyme dTDP-glucose 4,6-dehydratase , producing dTDP-4-keto-6-deoxy-glucose.[ 1] [ 2]
References
