Phosphopantetheine

Phosphopantetheine
Skeletal formula of
Space-filling model of the phosphopantetheine molecule as an anion (2- charge)
Identifiers
CAS Number
  • 2226-71-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:4222 checkY
ChemSpider
  • 103123 checkY
DrugBank
  • DB03912 checkY
MeSH phosphopantetheine
PubChem CID
  • 115254
UNII
  • NM39WU8OFM checkY
CompTox Dashboard (EPA)
  • DTXSID30897420 Edit this at Wikidata
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)/t9-/m0/s1 checkY
    Key: JDMUPRLRUUMCTL-VIFPVBQESA-N checkY
  • InChI=1/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)/t9-/m0/s1
    Key: JDMUPRLRUUMCTL-VIFPVBQEBX
  • O=C(NCCS)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)O
Properties
Chemical formula
 C11H23N2O7PS
Molar mass 358.349 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound

Phosphopantetheine, also known as 4'-phosphopantetheine, is a prosthetic group of several acyl carrier proteins including the acyl carrier proteins (ACP) of fatty acid synthases, ACPs of polyketide synthases, the peptidyl carrier proteins (PCP), as well as aryl carrier proteins (ArCP) of nonribosomal peptide synthetases (NRPS).[1] It is also present in formyltetrahydrofolate dehydrogenase.[2]

Subsequent to the expression of the apo acyl carrier protein, 4'-phosphopantetheine moiety is attached to a serine residue. The coupling involves formation of a phosphodiester linkage. This coupling is mediated by acyl carrier protein synthase (ACPS), a 4'-phosphopantetheinyl transferase.[3]

Phosphopantetheine prosthetic group covalently links to the acyl group via a high energy thioester bond. The flexibility and length of the phosphopantetheine chain (approximately 2 nm) allows the covalently tethered intermediates to access spatially distinct enzyme-active sites. This accessibility increases the effective molarity of the intermediate and allows an assembly line-like process.

See also

References

  1. ^ Elovson J, Vagelos PR (July 1968). "Acyl carrier protein. X. Acyl carrier protein synthetase". J. Biol. Chem. 243 (13): 3603–11. doi:10.1016/S0021-9258(19)34183-3. PMID 4872726.
  2. ^ Strickland KC, Hoeferlin LA, Oleinik NV, Krupenko NI, Krupenko SA (January 2010). "Acyl carrier protein-specific 4'-phosphopantetheinyl transferase activates 10-formyltetrahydrofolate dehydrogenase". J. Biol. Chem. 285 (3): 1627–33. doi:10.1074/jbc.M109.080556. PMC 2804320. PMID 19933275.
  3. ^ Beld, Joris; Sonnenschein, Eva C.; Vickery, Christopher R.; Noel, Joseph P.; Burkart, Michael D. (January 2014). "The Phosphopantetheinyl Transferases: Catalysis of a Posttranslational Modification Crucial for Life". Natural Product Reports. 31 (1): 61–108. doi:10.1039/c3np70054b. ISSN 0265-0568. PMC 3918677. PMID 24292120.


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