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Key Documents

14764

Sigma-Aldrich

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.

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 Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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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
Wanchai De-Eknamkul et al.
Phytochemistry, 62(3), 389-398 (2003-03-07)
A green callus culture of Croton sublyratus Kurz established from the leaf explants appeared to actively synthesize two well-known phytosterols, beta-sitosterol and stigmasterol. The phytosterol biosynthesis was highly active during the linear phase of the culture. Feeding of [1-13C]glucose into
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
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

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