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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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MetaCyc Compound: 4'-phosphopantetheine

Synonyms: phosphopantotheine, pantetheine 4'-phosphate, phosphopantetheine

Summary:
4'-phosphopantetheine is an essential prosthetic group of several acyl carrier proteins involved in pathways of primary and secondary metabolism. These include acyl carrier proteins (ACPs) of fatty acid synthases (FASs), ACPs of polyketide synthases (PKSs) and peptidyl carrier proteins (PCPs), and aryl carrier proteins of non-ribosomal peptide synthetases.

The free thiol moiety of 4'-phosphopantetheine serves to covalently bind the acyl reaction intermediates as thioesters during the multistep assembly of the monomeric precursors, typically acetyl, malonyl, and aminoacyl groups [Mootz01].

The 4'-phosphopantetheine moiety is derived from coenzyme A (CoA) and posttranslationally transferred onto an invariant serine side chain, as described in EC 2.7.8.7:

an apo-[acp] + coenzyme A → adenosine 3',5'-bisphosphate + a holo-[acyl-carrier protein]

This Mg2+-dependent conversion of the apoproteins to the holoproteins is catalyzed by the 4'-phosphopantetheine transferases. Organisms often have several such enzymes; for example, Escherichia coli have three enzyes, encoded by acpS, entD and acpT.

Chemical Formula: C11H21N2O7PS

Molecular Weight: 356.33 Daltons

Monoisotopic Molecular Weight: 358.0963583034 Daltons

SMILES: CC(C(O)C(=O)NCCC(NCCS)=O)(C)COP([O-])(=O)[O-]

InChI: InChI=1S/C11H23N2O7PS/c1-11(2,7-20-21(17,18)19)9(15)10(16)13-4-3-8(14)12-5-6-22/h9,15,22H,3-7H2,1-2H3,(H,12,14)(H,13,16)(H2,17,18,19)/p-2/t9-/m0/s1

InChIKey: InChIKey=JDMUPRLRUUMCTL-VIFPVBQESA-L

Unification Links: ChEBI:61723 , HMDB:HMDB01416 , IAF1260:36886 , KEGG:C01134 , MetaboLights:MTBLC61723 , PubChem:25245905

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -133.19473 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

coenzyme A biosynthesis I , coenzyme A biosynthesis II (mammalian) :
4'-phosphopantetheine + ATP + H+ → 3'-dephospho-CoA + diphosphate

Reactions known to produce the compound:

acyl carrier protein metabolism I :
a holo-[acyl-carrier protein] + H2O → 4'-phosphopantetheine + an apo-[acp]

citrate lyase activation :
[a holo citrate lyase acyl-carrier protein] + S-acetyl phosphopantetheine → an acetyl-[holo citrate lyase acyl-carrier protein] + 4'-phosphopantetheine

coenzyme A biosynthesis I , coenzyme A biosynthesis II (mammalian) :
R-4'-phosphopantothenoyl-L-cysteine + H+4'-phosphopantetheine + CO2

In Reactions of unknown directionality:

Not in pathways:
pantetheine + ATP = 4'-phosphopantetheine + ADP + H+
coenzyme A + H2O = adenosine 3',5'-bisphosphate + 4'-phosphopantetheine + 2 H+

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: L-seryl-AMP synthase , 6-deoxyerythronolide B synthase , acyl-CoA:malonyl-CoA C-acyltransferase , gramicidin S synthase , D-phenylalanyl-L-prolyl-L-valyl-L-ornithyl-L-leucyl-[NRPS-pcp] synthetase , D-phenylalanyl-[NRPS-pcp] synthetase , 3-amino-5,7-dihydroxy-6-methyl-8-[(2E,13E,15E)-5,7,9,11-tetrahydroxy-2,4,6,8,10,12,16-heptamethyl-17-oxooctadeca-2,13,15-trienoyl]-1,4,5,6-tetrahydronaphthalene-1,4-dione-[PKS-acp] synthase , 8-(3-amino-5-hydroxyphenyl)-8-hydroxy-3,7-dimethyloctane-2,4,6-trione -[PKS-acp] synthase , 1-(3-amino-5-hydroxyphenyl)ethan-1-one -[PKS-acp] synthase , acyl-CoA:malonyl-CoA C-acyltransferase , δ-(L-α-aminoadipyl)-L-cysteinyl-D-valine synthetase

Credits:
Revised 18-Feb-2011 by Caspi R , SRI International


References

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Mootz01: Mootz HD, Finking R, Marahiel MA (2001). "4'-phosphopantetheine transfer in primary and secondary metabolism of Bacillus subtilis." J Biol Chem 276(40);37289-98. PMID: 11489886


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Sun Dec 21, 2014, BIOCYC14A.