Phosphopantetheine

Phosphopantetheine

Identifiers
CAS Number	2226-71-3
3D model (Jmol)	Interactive image
ChEBI	CHEBI:4222
ChemSpider	103123
DrugBank	DB03912
MeSH	phosphopantetheine
PubChem	115254
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 Key: JDMUPRLRUUMCTL-VIFPVBQESA-N 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
SMILES 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

Phosphopantetheine, also known as 4'-Phosphopantetheine, is an essential prosthetic group of acyl carrier protein (ACP) and peptidyl carrier proteins (PCP) and aryl carrier proteins (ArCP) derived from Coenzyme A.^[1] It is also present in formyltetrahydrofolate dehydrogenase.^[2]

Functions

Phosphopantetheine fulfills two demands.

• First, the intermediates remain covalently linked to the synthases (or synthetases) in an energy-rich thiol ester linkage.
• Second, the flexibility and length of phosphopantetheine chain (approximately 2 nm) allows the covalently tethered intermediates to have access to spatially distinct enzyme active sites.

See also

• pantothenic acid
• fatty acid synthase

References

1. Elovson J, Vagelos PR (July 1968). "Acyl carrier protein. X. Acyl carrier protein synthetase". J. Biol. Chem. 243 (13): 3603–11. 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.