An intermediate for tetrahydro-L-biopterin
Related Products
Enantiomer(s)
34201D-Biopterin
Isomer(s)
298197-Biopterin
Technical Support & Resources

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Product Type

Biochemicals

Research Area

L-Biopterin

Item No. 10007662

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-4(1H)-pteridinone
CAS Number
22150-76-1
Synonyms
  • L-erythro-Biopterin
  • NSC 339699
Molecular Formula
C9H11N5O3
Formula Weight
237.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 0.3 mg/mlDMSO: 1 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml
λmax
276, 348 nm
SMILES
NC(N=C1C2=NC([C@@H](O)[C@@H](O)C)=CN1[H])=NC2=O
InChi Code
InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6-/m0/s1
InChi Key
LHQIJBMDNUYRAM-DZSWIPIPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    10 mg

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    25 mg

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    50 mg

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    Product Description

    L-Biopterin is the oxidized form of tetrahydro-L-biopterin (BH4), a nitric oxide synthase (NOS) cofactor. L-Biopterin can be reduced to BH4 via thioredoxin reductase followed by dihydropteridine reductase or reduced glutathione. It is extremely toxic to human melanocytes in culture (IC50 = 0.2 µM after 48 hrs).1 L-Biopterin is rarely found under physiological conditions except in the epidermis of patients with the depigmentation disorder Vitiligo.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Schallreuter, K.U., Büttner, G., Pittelkow, M.R., et al. Cytotoxicity of 6-biopterin to human melanocytes. Biochem. Biophys. Res. Commun. 204(1), 43-48 (1994).

    2. Moore, J., Wood, J.M., and Schallreuter, K.U. Evidence for specific complex formation between α-melanocyte stimulating hormone and 6(R)-L-erythro-5,6,7,8-tetrahydrobiopterin using near infared fourier transform raman spectroscopy. Biochemistry 38(46), 15317-15324 (1999).