An intermediate in CoA biosynthesis and salvage
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4’-Phosphopantetheine

Item No. 44534

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R)-2-hydroxy-N-[3-[(2-mercaptoethyl)amino]-3-oxopropyl]-3,3-dimethyl-4-(phosphonooxy)-butanamide
CAS Number
2226-71-3
Synonyms
  • 4'-PP
  • 4-PPanSH
  • PPant
Molecular Formula
C11H23N2O7PS
Formula Weight
358.3
Purity
≥95%
Formulation (Request formulation change)
A semi-solid
SMILES
SCCNC(CCNC([C@H](O)C(C)(C)COP(O)(O)=O)=O)=O
InChi Code
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
InChi Key
JDMUPRLRUUMCTL-VIFPVBQESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $68

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    5 mg

    $187

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    10 mg

    $306

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    Product Description

    4’-Phosphopantetheine is an intermediate in the coenzyme A (CoA; Item Nos. 16147 | 21722 | 21499) biosynthesis and salvage pathways.1 It is also an integral cofactor in phosphopantetheinylation, a post-translational modification to serine residues in inactive apo-synthases, such as fatty acid synthases and polyketide synthases, that converts them into active holo-synthases.2 4’-Phosphopanthetheine increases pyruvate dehydrogenase (PDH) and mitochondrial complex I activity and transferrin receptor protein 1 (TfR1) levels in the globus pallidus in a Pank2 knockout mouse model of pantothenate kinase-associated neurodegeneration (PKAN), an inborn error of CoA metabolism characterized by mutations in pantothenate kinase 2 (PanK2), the enzyme that converts pantetheine to 4’-phosphopantetheine.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. de Villiers, M., Barnard, L., Koekemoer, L., et al. Variation in pantothenate kinase type determines the pantothenamide mode of action and impacts on coenzyme A salvage biosynthesis. FEBS J. 281(20), 4731-4753 (2014).

    2. Beld, J., Sonnenschein, E.C., Vickery, C.R., et al. The phosphopantetheinyl transferases: Catalysis of a post-translational modification crucial for life. Nat. Prod. Rep. 31(1), 61-108 (2014).

    3. Jeong, S.Y., Hogarth, P., Placzek, A., et al. 4'-Phosphopantetheine corrects CoA, iron, and dopamine metabolic defects in mammalian models of PKAN. EMBO Mol. Med. 11(12), e10489 (2019).