A cofactor for production of aromatic amino acids, neurotransmitters, and nitric oxide
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(6R)-5,6,7,8-tetrahydro-L-Biopterin (hydrochloride)

Item No. 81880

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-amino-6R-(1R,2S-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinone, dihydrochloride
CAS Number
69056-38-8
Synonyms
  • BH4
Molecular Formula
C9H15N5O3 • 2HCl
Formula Weight
314.2
Purity
≥99%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: >3 mg/mlDMSO: >5 mg/mlPBS (pH 7.2): >10 mg/ml
λmax
220, 268 nm
SMILES
C[C@H](O)[C@H](O)[C@@](N1[H])([H])CN([H])C(N([H])C(N)=N2)=C1C2=O.Cl.Cl
InChi Code
InChI=1S/C9H15N5O3.2ClH/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7;;/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17);2*1H/t3-,4+,6-;;/m0../s1
InChi Key
RKSUYBCOVNCALL-NTVURLEBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $44

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    10 mg

    $84

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    50 mg

    $154

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    100 mg

    $220

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    Product Description

    (6R)-5,6,7,8-tetrahydro-L-Biopterin (hydrochloride) (BH4) is a cofactor that, in the presence of enzyme site iron, binds to phenylalanine hydroxylase, tryptophan or tyrosine hydroxylase, and nitric oxide synthase (NOS), to facilitate the production of aromatic amino acids, neurotransmitters, and nitric oxide (NO), respectively.1,2,3 It is formed de novo from GTP with GTP cyclohydrolase-1 (GCH1) catalyzing the rate limiting conversion of GTP to 7,8-dihydroneopterin (NH2TP) followed by subsequent processing by TS and SPR to convert NH2TP to BH4.4,3 BH4 acts as a radical-trapping antioxidant that inhibits phospholipid oxidation in lipid membranes.4 It inhibits IKE- or RSL3-induced ferroptosis in HT-1080 cells (EC50s = 21 and 69 µM), as well as ferroptosis induced by knockout of glutathione peroxidase (Gpx4-/-) in immortalized mouse fibroblasts.3 BH4 also reduces RLS3-induced lipid peroxidation in murine fibroblasts and HT-1080 cells when used at a concentration of 50 µM.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kappock, T.J., and Caradonna, J.P. Pterin-dependent amino acid hydroxylases. Chem. Rev. 96(7), 2659-2756 (1996).

    2. Mayer, B., and Werner, E.R. In search of a function for tetrahydrobiopterin in the biosynthesis of nitric oxide. N.-S. Arch. Pharmacol. 351(5), 453-463 (1995).

    3. Kraft, V.A.N., Bezjian, C.T., Pfeiffer, S., et al. GTP cyclohydrolase 1/tetrahydrobiopterin counteract ferroptosis through lipid remodeling. ACS Cent. Sci. 6(1), 41-53 (2020).

    4. Soula, M., Weber, R.A., Zilka, O., et al. Metabolic determinants of cancer cell sensitivity to canonical ferroptosis inducers. Nat. Chem. Biol. 16(12), 1351-1360 (2020).

    Product Citations

    Woldman, Y.Y., Sun, J.Z., J.L., and Khramtsov, V.V. Direct chemiluminescence detection of nitric oxide in aqueous solutions using the natural nitric oxide target soluble guanylyl cyclase. Free Radic. Biol. Med. 47(10), 1339-1345 (2009).