Deoxythymidine diphosphate-L-rhamnose

[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl]methyl (2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl dihydrogen diphosphate (non-preferred name)

Formula: C16H26N2O15P2 (548.0808)
Chinese Name: 脱氧胸苷二磷酸-L-鼠李糖
BioDeep ID: BioDeep_00000000817 ( View LC/MS Profile)
SMILES: [C@@H]1([C@@H]([C@@H]([C@H]([C@H](O1)O[P@@](=O)(O[P@](=O)(OC[C@@H]1[C@@H](C[C@@H](O1)n1cc(c(=O)[nH]c1=O)C)O)O)O)O)O)O)C



Found 8 Sample Hits

m/z Adducts Species Organ Scanning Sample
513.0588 [M+H-2H2O]+
PPM:16
Mytilus edulis mantle MALDI (DHB)
20190201_MS38_Crassostrea_Mantle_350-1500_DHB_pos_A28_10um_270x210 - MTBLS2960
Resolution: 10μm, 270x210

Description

549.0796 [M+H]+
PPM:15.5
Mytilus edulis mantle MALDI (DHB)
20190201_MS38_Crassostrea_Mantle_350-1500_DHB_pos_A28_10um_270x210 - MTBLS2960
Resolution: 10μm, 270x210

Description

571.0643 [M+Na]+
PPM:10.1
Mytilus edulis mantle MALDI (DHB)
20190201_MS38_Crassostrea_Mantle_350-1500_DHB_pos_A28_10um_270x210 - MTBLS2960
Resolution: 10μm, 270x210

Description

513.0583 [M+H-2H2O]+
PPM:16.9
Mytilus edulis gill MALDI (DHB)
20190202_MS38_Crassostrea_Gill_350-1500_DHB_pos_A25_11um_305x210 - MTBLS2960
Resolution: 11μm, 305x210

Description

single cell layer class_4 is the gill structure cells, metabolite ion 534.2956 is the top representive ion of this type of cell

571.0638 [M+Na]+
PPM:11
Mytilus edulis gill MALDI (DHB)
20190202_MS38_Crassostrea_Gill_350-1500_DHB_pos_A25_11um_305x210 - MTBLS2960
Resolution: 11μm, 305x210

Description

single cell layer class_4 is the gill structure cells, metabolite ion 534.2956 is the top representive ion of this type of cell

513.0584 [M+H-2H2O]+
PPM:16.7
Mytilus edulis mantle MALDI (DHB)
20190216_MS38_Mytilus_mantle_350-1500_DHB_pos_A26_10um_275x210 - MTBLS2960
Resolution: 10μm, 275x210

Description

549.0791 [M+H]+
PPM:16.4
Mytilus edulis mantle MALDI (DHB)
20190216_MS38_Mytilus_mantle_350-1500_DHB_pos_A26_10um_275x210 - MTBLS2960
Resolution: 10μm, 275x210

Description

571.0639 [M+Na]+
PPM:10.8
Mytilus edulis mantle MALDI (DHB)
20190216_MS38_Mytilus_mantle_350-1500_DHB_pos_A26_10um_275x210 - MTBLS2960
Resolution: 10μm, 275x210

Description


Deoxythymidine diphosphate-L-rhamnose (dTDP-L-rhamnose) is the precursor of L-rhamnose, a saccharide required for the virulence of some pathogenic bacteria. In gram-negative bacteria such as Salmonella enterica, Vibrio cholerae, or Escherichia coli 075:K5, L-rhamnose is an important residue in the O-antigen of lipopolysaccharides, which are essential for resistance to serum killing and colonization. In gram-positive bacteria such as streptococci, the capsule is a recognized virulence factor. For example, L-rhamnose is known to be present in the capsule of Streptococcus suis, a causative agent of meningitis in humans. In Streptococcus mutans, L-rhamnose containing polysaccharides have been implicated in tooth surface colonization and adherence to kidney, muscle, and heart tissues. In mycobacteria, L-rhamnose is fundamental to the structural integrity of the cell wall since it connects the inner peptidoglycan layer to the arabinogalactan polysaccharides. dTDP-L-rhamnose is synthesized from glucose-1-phosphate and deoxythymidine triphosphate (dTTP) via a pathway involving four distinct enzymes. Whereas common sugars such as glucose, fructose, and mannose are all D-configured, bacteria commonly utilize the L-configured carbohydrates in pharmacologically active compounds and their cell-wall structures. The bacterial cell wall is unique to bacteria; neither the cell wall nor the enzymes and chemical intermediates in its formation have analogues in humans. The enzymes involved in dTDP-L-rhamnose synthesis are potential targets for the design of new therapeutic agents (PMID: 10802738, 12773151). 2-deoxy-thymidine-beta-l-rhamnose, also known as dtdp-6-deoxy-L-mannose or thymidine diphosphate-L-rhamnose, is a member of the class of compounds known as pyrimidine nucleotide sugars. Pyrimidine nucleotide sugars are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. 2-deoxy-thymidine-beta-l-rhamnose is soluble (in water) and a moderately acidic compound (based on its pKa). 2-deoxy-thymidine-beta-l-rhamnose can be found in a number of food items such as black salsify, dill, roman camomile, and tea leaf willow, which makes 2-deoxy-thymidine-beta-l-rhamnose a potential biomarker for the consumption of these food products. DTDP-beta-L-rhamnose is the beta-anomer of dTDP-L-rhamnose. It has a role as an Escherichia coli metabolite. It is functionally related to a dTDP-L-mannose. It is a conjugate acid of a dTDP-6-deoxy-beta-L-mannose(2-). Deoxythymidine diphosphate-L-rhamnose is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). The beta-anomer of dTDP-L-rhamnose.