Phosphopantetheine

Phosphopantetheine
Identifiers
CAS Number	2226-71-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:4222 ;
ChemSpider	103123 ;
DrugBank	DB03912 ;
MeSH	phosphopantetheine
PubChem CID	115254;
UNII	NM39WU8OFM ;
CompTox Dashboard (EPA)	DTXSID30897420 ;
	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.

Elovson J, Vagelos PR (July 1968). "Acyl carrier protein. X. Acyl carrier protein synthetase". J. Biol. Chem. 243 (13): 3603–11. PMID 4872726.
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.

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