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
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.
Other Notes
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.
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Storage Class Code
13 - Non Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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C Rieder et al.
The Journal of biological chemistry, 273(29), 18099-18108 (1998-07-11)
The biosynthesis of verrucosan-2beta-ol in the green phototrophic eubacterium Chloroflexus aurantiacus was investigated by in vivo incorporation of singly or doubly 13C-labeled acetate. The 13C labeling of the isolated diterpene was analyzed by one- and two-dimensional NMR spectroscopy. The 13C-labeling
Felix Rohdich et al.
Proceedings of the National Academy of Sciences of the United States of America, 100(4), 1586-1591 (2003-02-07)
Earlier in vivo studies have shown that the sequential action of the IspG and IspH proteins is essential for the reductive transformation of 2C-methyl-d-erythritol 2,4-cyclodiphosphate into dimethylallyl diphosphate and isopentenyl diphosphate via 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate. A recombinant fusion protein comprising maltose
W Eisenreich et al.
Trends in plant science, 6(2), 78-84 (2001-02-15)
Recently, a mevalonate-independent pathway was discovered in bacteria and plants that leads to the formation of isopentenyl diphosphate and dimethylallyl diphosphate, the two basic precursors of isoprenoids. Although many details of the widely distributed pathway are unknown, some intermediates, mechanisms
Andréa Hemmerlin et al.
Plant physiology, 142(2), 441-457 (2006-08-22)
Plants are able to integrate exogenous 1-deoxy-D-xylulose (DX) into the 2C-methyl-D-erythritol 4-phosphate pathway, implicated in the biosynthesis of plastidial isoprenoids. Thus, the carbohydrate needs to be phosphorylated into 1-deoxy-D-xylulose 5-phosphate and translocated into plastids, or vice versa. An enzyme capable
W Eisenreich et al.
Cellular and molecular life sciences : CMLS, 61(12), 1401-1426 (2004-06-16)
The mevalonate pathway for the biosynthesis of the universal terpenoid precursors, isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), is known in considerable detail. Only recently, the existence of a second mevalonate-independent pathway for the biosynthesis of IPP and DMAPP was
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