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Escherichia coli K-12 substr. MG1655 Compound: D-arabinose 5-phosphate

Systematic Name: D-arabinose, 5-(dihydrogen phosphate)

Synonyms: D-arabinose-5-P, arabinose-5P, D-A-5-P, arabinose 5-phosphate, arabinose-5-P

Superclasses: all carbohydrates a carbohydrate a glycan a carbohydrate derivative a sugar phosphate a pentose phosphate a pentose 5-phosphate
all carbohydrates a carbohydrate a glycan a carbohydrate derivative a sugar phosphate a sugar 5-phosphate a pentose 5-phosphate

Chemical Formula: C5H9O8P

Molecular Weight: 228.1 Daltons

Monoisotopic Molecular Weight: 230.01915383989999 Daltons

D-arabinose 5-phosphate compound structure

SMILES: [CH](=O)C(C(C(COP([O-])([O-])=O)O)O)O

InChI: InChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h1,3-5,7-9H,2H2,(H2,10,11,12)/p-2/t3-,4-,5+/m1/s1

InChIKey: InChIKey=PPQRONHOSHZGFQ-WDCZJNDASA-L

Unification Links: CAS:13137-52-5 , ChEBI:57693 , ChemSpider:19951162 , HMDB:HMDB11734 , IAF1260:36837 , KEGG:C01112 , PubChem:23615240

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -392.04

Reactions known to consume the compound:

CMP-3-deoxy-D-manno-octulosonate biosynthesis I :
D-arabinose 5-phosphate + phosphoenolpyruvate + H2O → 3-deoxy-D-manno-octulosonate 8-phosphate + phosphate

Not in pathways:
a sugar phosphate + H2O → a sugar + phosphate

Reactions known to both consume and produce the compound:

CMP-3-deoxy-D-manno-octulosonate biosynthesis I :
D-arabinose 5-phosphate ↔ D-ribulose 5-phosphate

In Transport reactions:
a [PTS enzyme I]-Nπ-phospho-L-histidine + a sugar[periplasmic space] → a [PTS enzyme I]-L-histidine + a sugar phosphate[cytosol]

Enzymes inhibited by D-arabinose 5-phosphate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: transketolase [Sprenger95a] , transaldolase [Sprenger95] , fructose 6-phosphate aldolase [Schurmann01]

Inhibitor (Mechanism unknown) of: ribose-5-phosphate isomerase A [Zhang03b]


References

Schurmann01: Schurmann M, Sprenger GA (2001). "Fructose-6-phosphate aldolase is a novel class I aldolase from Escherichia coli and is related to a novel group of bacterial transaldolases." J Biol Chem 2001;276(14);11055-61. PMID: 11120740

Sprenger95: Sprenger GA, Schorken U, Sprenger G, Sahm H (1995). "Transaldolase B of Escherichia coli K-12: cloning of its gene, talB, and characterization of the enzyme from recombinant strains." J Bacteriol 1995;177(20);5930-6. PMID: 7592346

Sprenger95a: Sprenger GA, Schorken U, Sprenger G, Sahm H (1995). "Transketolase A of Escherichia coli K12. Purification and properties of the enzyme from recombinant strains." Eur J Biochem 1995;230(2);525-32. PMID: 7607225

Zhang03b: Zhang R, Andersson CE, Savchenko A, Skarina T, Evdokimova E, Beasley S, Arrowsmith CH, Edwards AM, Joachimiak A, Mowbray SL (2003). "Structure of Escherichia coli ribose-5-phosphate isomerase: a ubiquitous enzyme of the pentose phosphate pathway and the Calvin cycle." Structure 11(1);31-42. PMID: 12517338


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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