1-Deoxy-D-xylulose 5-phosphate

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1-Deoxy-d-xylulose 5-phosphate
DOXP.png
Names
IUPAC name
1-Deoxy-D-xylulose 5-(dihydrogen phosphate)
Systematic IUPAC name
(2R,3S)-2,3-Dihydroxy-4-oxopentyl dihydrogen phosphate
Other names
DOXP
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
KEGG
MeSH 1-deoxy-D-xylulose+5-phosphate
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: AJPADPZSRRUGHI-RFZPGFLSSA-N Yes check.svgY
  • 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/s1
    Key: AJPADPZSRRUGHI-RFZPGFLSBQ
  • O=P(O)(O)OC[C@@H](O)[C@H](O)C(=O)C
Properties
C5H11O7P
Molar mass 214.11
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1-Deoxy-d-xylulose 5-phosphate is a biosynthetic intermediate in the non-mevalonate pathway. [1]

Function

The enzyme involved in making 1-deoxy-d-xylulose 5-phosphate (DXP) is DXP synthase. [2] The mechanism follows a catalysis of decarboxylative condensation of pyruvate and d-glyceraldehyde 3-phosphate to produce DXP. [2] [3] In addition, the molecule is involved in making thiamine (vitamin B1) and pyridoxol (vitamin B6). [2]

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. [1]

See also

References

  1. 1 2 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.
  2. 1 2 3 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 .
  3. ↑ 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.
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