1-Deoxy-D-xylulose 5-phosphate

(Redirected from 1-deoxy-D-xylulose 5-phosphate)

1-Deoxy-d-xylulose 5-phosphate
Names

IUPAC name (2,3-dihydroxy-4-oxopentyl) dihydrogen phosphate
Other names DOXP
Identifiers
CAS Number	190079-18-6
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16493
ChemSpider	391473
DrugBank	DB02496
KEGG	C11437
MeSH	1-deoxy-D-xylulose+5-phosphate
PubChem CID	443201
UNII	I4C288B3TN
CompTox Dashboard (EPA)	DTXSID90940547
InChI 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/s1Key: AJPADPZSRRUGHI-RFZPGFLSSA-N InChI=1/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/s1Key: AJPADPZSRRUGHI-RFZPGFLSBQ
SMILES O=P(O)(O)OC(O)(O)C(=O)C
Properties
Chemical formula	C₅H₁₁O₇P
Molar mass	214.11
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

1-Deoxy-d-xylulose 5-phosphate is a biosynthetic intermediate in the non-mevalonate pathway.

Function

The enzyme involved in making 1-deoxy-d-xylulose 5-phosphate (DXP) is DXP synthase. The mechanism follows a catalysis of decarboxylative condensation of pyruvate and d-glyceraldehyde 3-phosphate to produce DXP. In addition, the molecule is involved in making thiamine (vitamin B₁) and pyridoxol (vitamin B₆).

The non-mevalonate pathway intermediate 1-deoxy-d-xylulose 5-phosphate (DXP) also acts as a precursor in making isoprenoids in many species such as bacteria, plants, and apicomplexan parasites, contributing to biological diversity.

References

^ Bartee D, Freel Meyers CL (October 2018). "Toward Understanding the Chemistry and Biology of 1-Deoxy-d-xylulose 5-Phosphate (DXP) Synthase: A Unique Antimicrobial Target at the Heart of Bacterial Metabolism". Accounts of Chemical Research. 51 (10): 2546–2555. doi:10.1021/acs.accounts.8b00321. PMC 6309272. PMID 30203647.
^ Xiang S, Usunow G, Lange G, Busch M, Tong L (January 2007). "Crystal Structure of 1-Deoxy-d-xylulose 5-Phosphate Synthase, a Crucial Enzyme for Isoprenoids Biosynthesis". Journal of Biological Chemistry. 282 (4): 2676–2682. doi:10.1074/jbc.M610235200.
Bartee D, Freel Meyers CL (2018-07-24). "Targeting the Unique Mechanism of Bacterial 1-Deoxy- d -xylulose-5-phosphate Synthase". Biochemistry. 57 (29): 4349–4356. doi:10.1021/acs.biochem.8b00548. ISSN 0006-2960. PMC 6057799. PMID 29944345.

Cholesterol and steroid metabolic intermediates

Mevalonate pathway

to HMG-CoA	Acetyl-CoA Acetoacetyl-CoA HMB HMB-CoA HMG-CoA
Ketone bodies	Acetone Acetoacetic acid β-Hydroxybutyric acid
to DMAPP	Mevalonic acid Phosphomevalonic acid 5-Diphosphomevalonic acid Isopentenyl pyrophosphate Dimethylallyl pyrophosphate
Geranyl-	Geranyl pyrophosphate Geranylgeranyl pyrophosphate
Carotenoid	Prephytoene diphosphate Phytoene

Non-mevalonate pathway

To Cholesterol

From Cholesterol
to Steroid hormones

Nonhuman

To Sitosterol	Cycloartenol Cycloeucalenol Obtusifoliol 4α-methylfecosterol Isofucosterol 24-Methylenelophenol Sitosterol More Phytosterols see here instead.
To Ergocalciferol	Fecosterol Episterol Ergostatrienol Ergostatetraenol Ergosterol Ergocalciferol

Categories:

Misplaced Pages