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Phosphopantetheine

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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]

Phosphopantetheine
Skeletal formula of
Space-filling model of the phosphopantetheine molecule as an anion (2- charge)
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
MeSH phosphopantetheine
UNII
  • 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
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).
☒N verify (what is checkY☒N ?)

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

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References

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  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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