L-Biopterin

Product Name: L-Biopterin
CAS No. : 22150-76-1 
Synonym: NSC 339699; 6-Biopterin;L-erythro-Biopterin;(1'R,2'S)-Biopterin
Chemical Name: 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]pteridin-4(1H)-one;2-amino-7-(1,2-dihydroxypropyl)pteridin-4(1H)-one
Molecular Formula: C9H11N5O3 
Molecular Weight: 237.09 
Appearance: Colorless to pale yellow powder
Purity: >98% HPLC 
 

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). L-Biopterin is rarely found under physiological conditions except in the epidermis of patients with the depigmentation disorder Vitiligo.

L-Biopterin is an important cofactor in the production of many essential neurotransmitters, such as dopamine, seratonin and epinephrine, and plays an important role in the production of nitric oxide in the body. It is produced as an oxidation product by the melanogenesis regulating cofactor (6R)5,6,7,8 tetrahydrobiopterin (6-BH4). L-Biopterin has been shown to be cytotoxic to melanocytes in vitro, and may be a useful noninvasive biomarker.

Applications: A pteridine widely distributed in nature; naturally occurring as the L-erythro-form. Considered as a growth factor for some insects. Fluoresces with a blue color in alkaline solution. A cofactor in the production of many neurotransmitters and nitric oxide.

6-Biopterin is an oxidation product from the melanogenesis regulating cofactor (6R)5,6,7,8 tetrahydrobiopterin (6-BH4). In vitro, 6-Biopterin is cytotoxic to melanocytes. However, in vivo, 6-Biopterin is rapidly and sequentially reduced back to 6-GH4 via q-BH2. Recent studies suggest that 6-Biopterin among other pteridines may be a useful non-invasive biomarker for cancer.

Synonyms: NSC 339699; 6-Biopterin; L-Erythro-biopterin; (1'R,2'S)-Biopterin;2-Amino-4-hydroxy-6-(1,2-dihydroxypropyl)pteridine;2-amino-6-(1,2-dihydroxypropyl)pteridin-4(1H)-one;2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]pteridin-4(1H)-one;2-amino-7-(1,2-dihydroxypropyl)pteridin-4(1H)-one
CAS No: 22150-76-1
Molecular Formula: C₉H₁₁N₅O₃
Molecular Weight: 237.22
Appearance: Colorless to pale yellow powder
Storage: Store in cool dark place keep away from the sunshine light.

Biochemical functions: Biopterin has two isomers (D- and L-biopterin). We sell only L-Biopterin. The hydrogenated forms of biopterin i.e. dihydrobiopterin and tetrahydrobiopterin are involved in many important biochemical functions in the human body, among which are the hydroxylation of tyrosine, phenylalanine and tryptophan.
Solubility: Biopterin is very slightly soluble in water. The solubility of biopterin is about 0.01 g per 100 g of water (22°C ). Concentrated solutions of biopterin may be prepared using 0.05M NaOH. Ultrasonication may be used to improve dissolution.

 Analytical methods:

    HPLC conditions:  Column: Waters Spherisorb S5 ODS1

                          Eluant: 10mM Na₂HPO₄ PH 6-methanol, (19:1)

                          Flow rate: 1ml/min

                          Wavelength: 254nm

                          Solution: 2mg/ml 0.05 M NaOH

    TLC conditions:    Stationary phase: cellulose

                          Eluant: water

Specifications: Purity: HPLC >98.0%

                           TLC    one blue fluorescent spot at 366nm
Stability: Biopterin is light sensitive. Biopterin contains half a mole of water. It can be stored for several years, dry, in tightly closed bottle coloured , at - 20°C or colder.

Storage: Keep the powder dry in tightly closed bottle coloured , at - 20°C . Biopterin can be transported without the use of dry ice. In tightly closed bottle, wrapped in aluminium foil, it is stable at ambient temperature for several months.

Uses: Biopterin is an important  standard for analytical work involving tetrahydrobiopterin and dihydrobiopterin. It is not suitable for the addition to nutritional supplements .

Safety information: Biopterin is known to be safe and there are no special precautions required in handling this product.

Remarks: The information in this publication is based on our current knowledge and experience. It does not relieve users or processors from carrying out their own precautions and tests.