14764
1-Deoxy-D-xylulose
≥80% (TLC)
Synonym(s):
(3S,4R)-3,4,5-Trihydroxy-2-pentanone, 1-Deoxy-D-threo-2-pentulose
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About This Item
Empirical Formula (Hill Notation):
C5H10O4
CAS Number:
Molecular Weight:
134.13
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25
Recommended Products
assay
≥80% (TLC)
form
liquid
optical activity
[α]/D +31.0±3.0°, c = 1 in H2O
storage temp.
−20°C
SMILES string
CC(=O)[C@@H](O)[C@H](O)CO
InChI
1S/C5H10O4/c1-3(7)5(9)4(8)2-6/h4-6,8-9H,2H2,1H3/t4-,5-/m1/s1
InChI key
IGUZJYCAXLYZEE-RFZPGFLSSA-N
Biochem/physiol Actions
Metabolite of the non-mevalonate pathway, generally found in prokaryotes, as precursor to isoprenoids as well as non-isoprenoids like vitamins. As this pathway is not present in humans, it is of interest for the development of bacterium-specific drugs in the search for treatments of infectious diseases.
Linkage
In E. coli, 1-deoxy-D-xylulose is converted into 1-deoxy-D-xylulose 5-phosphate by phosphorylation of the C-5 hydroxy group by D-xylulokinase.
Other Notes
To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.
Storage Class
13 - Non Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Certificates of Analysis (COA)
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Andréa Hemmerlin et al.
The Journal of biological chemistry, 278(29), 26666-26676 (2003-05-09)
In plants, two pathways are utilized for the synthesis of isopentenyl diphosphate, the universal precursor for isoprenoid biosynthesis. The key enzyme of the cytoplasmic mevalonic acid (MVA) pathway is 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGR). Treatment of Tobacco Bright Yellow-2 (TBY-2) cells
Ines Neundorf et al.
Chembiochem : a European journal of chemical biology, 4(11), 1201-1205 (2003-11-13)
Upon feeding of [2-(13)C,4-(2)H]-1-deoxy-D-xylulose to Streptomyces ghanaensis, the deuterium label was retained exclusively at positions C-7 and C-17 in the moenocinol part of the moenomycin antibiotics. This result vindicates the hypothesis that the C(25) structure of moenocinol is assembled from
Phosphorylation of 1-deoxy-D-xylulose by D-xylulokinase of Escherichia coli.
Wungsintaweekul, J.
European Journal of Biochemistry, 268, 310?316-310?316 (2001)
J Schwender et al.
Planta, 212(3), 416-423 (2001-04-06)
The biosynthesis of the C5 building block of isoprenoids, isopentenyl diphosphate (IPP), proceeds in higher plants via two basically different pathways; in the cytosolic compartment sterols are formed via mevalonate (MVA), whereas in the plastids the isoprenoids are formed via
Jiaqi Liu et al.
Frontiers in plant science, 8, 2082-2082 (2017-12-23)
As one type of the most important alkaloids in the world, terpenoid indole alkaloids (TIAs) show a wide range of pharmaceutical activities that are beneficial for clinical treatments.
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