Phosphopantetheine

Phosphopantetheine

Identifiers
CAS number	2226-71-3
PubChem	115254
ChemSpider	103123^Y
DrugBank	DB03912
MeSH	phosphopantetheine
ChEBI	CHEBI:4222^Y
Jmol-3D images	Image 1
SMILES O=C(NCCS)CCNC(=O)[C@H](O)C(C)(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)/t9-/m0/s1^Y Key: JDMUPRLRUUMCTL-VIFPVBQESA-N^Y 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
Properties
Molecular formula	C₁₁H₂₃N₂O₇PS
Molar mass	358.349 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2804320.