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13368

Sigma-Aldrich

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)
Beilstein:
8367371
MDL number:
UNSPSC Code:
12352201
NACRES:
NA.25

Quality Level

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

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

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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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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. &
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
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
B M Lange et al.
Proceedings of the National Academy of Sciences of the United States of America, 95(5), 2100-2104 (1998-04-16)
Isopentenyl diphosphate, the common precursor of all isoprenoids, has been widely assumed to be synthesized by the acetate/mevalonate pathway in all organisms. However, based on in vivo feeding experiments, isopentenyl diphosphate formation in several eubacteria, a green alga, and plant

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