13368
1-Deoxy-D-xylulose-5-phosphate sodium salt
≥99.0% (TLC)
Synonym(s):
DXP sodium salt
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About This Item
Empirical Formula (Hill Notation):
C5H11O7P · xNa+
CAS Number:
Molecular Weight:
214.11 (free acid basis)
MDL number:
UNSPSC Code:
12352201
NACRES:
NA.25
Beilstein/REAXYS Number:
8367371
Product Name
1-Deoxy-D-xylulose-5-phosphate sodium salt, ≥99.0% (TLC)
SMILES string
[P](=O)(OC[C@@H](O)[C@H](O)C(=O)C)(O)O
InChI
1S/C5H11O7P/c1-3(6)5(8)4(7)2-12-13(9,10)11/h4-5,7-8H,2H2,1H3,(H2,9,10,11)/t4-,5-/m1/s1
InChI key
AJPADPZSRRUGHI-RFZPGFLSSA-N
assay
≥99.0% (TLC)
form
powder
optical activity
[α]/D 37.0±3.0°, c = 0.1 in 0.1 M HCl
color
white
storage temp.
−20°C
Quality Level
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Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Application
1-Deoxy-D-xylulose-5-phosphate is used as a substrate for the identification, differentiation and characterization of procaryotic 1-Deoxy-D-xylulose-5-phosphate reductoisomerase(s) (Dxr) which catalyze the first committed step of the nonmevalonate pathway (NMP) for isoprenoid biosynthesis.
Biochem/physiol Actions
Metabolite of the non-mevalonate pathway, generally found in prokaryotes, as precursor to isoprenoids as well asnon-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
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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B M Lange et al.
Proceedings of the National Academy of Sciences of the United States of America, 97(24), 13172-13177 (2000-11-15)
Isopentenyl diphosphate (IPP) is the central intermediate in the biosynthesis of isoprenoids, the most ancient and diverse class of natural products. Two distinct routes of IPP biosynthesis occur in nature: the mevalonate pathway and the recently discovered deoxyxylulose 5-phosphate (DXP)
G A Sprenger et al.
Proceedings of the National Academy of Sciences of the United States of America, 94(24), 12857-12862 (1997-12-16)
In Escherichia coli, 1-deoxy-D-xylulose (or its 5-phosphate, DXP) is the biosynthetic precursor to isopentenyl diphosphate [Broers, S. T. J. (1994) Dissertation (Eidgenössische Technische Hochschule, Zürich)], thiamin, and pyridoxol [Himmeldirk, K., Kennedy, I. A., Hill, R. E., Sayer, B. G. &
Hartmut K. Lichtenthaler
Annual review of plant physiology and plant molecular biology, 50, 47-65 (2004-03-12)
In plants the biosynthesis of prenyllipids and isoprenoids proceeds via two independent pathways: (a) the cytosolic classical acetate/mevalonate pathway for the biosynthesis of sterols, sesquiterpenes, triterpenoids; and (b) the alternative, non-mevalonate 1-deoxy-d-xylulose-5-phosphate (DOXP) pathway for the biosynthesis of plastidic isoprenoids
J Schwender et al.
FEBS letters, 414(1), 129-134 (1997-09-26)
In further substantiating the novel mevalonate-independent pathway for isoprenoid biosynthesis, which generates isopentenyl diphosphate (IPP) via 1-deoxy-D-xylulose-5-phosphate, labeling experiments with 1-[2H(1)]deoxy-D-xylulose were performed with various higher plants and algae: efficient incorporation was observed into isoprene emitted by Populus, Chelidonium, and
H Jomaa et al.
Science (New York, N.Y.), 285(5433), 1573-1576 (1999-09-08)
A mevalonate-independent pathway of isoprenoid biosynthesis present in Plasmodium falciparum was shown to represent an effective target for chemotherapy of malaria. This pathway includes 1-deoxy-D-xylulose 5-phosphate (DOXP) as a key metabolite. The presence of two genes encoding the enzymes DOXP
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