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MedKoo Cat#: 540047 | Name: Biopterin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Biopterin plays an essential role in nitric oxide synthase catalysis, not only as an allosteric modulator but also as a cofactor involved in electron flow through the enzyme. In absence of biopterin, all isoforms of nitric oxide synthases are virtually inactive.

Chemical Structure

Biopterin
Biopterin
CAS#22150-76-1

Theoretical Analysis

MedKoo Cat#: 540047

Name: Biopterin

CAS#: 22150-76-1

Chemical Formula: C9H11N5O3

Exact Mass: 237.0862

Molecular Weight: 237.21

Elemental Analysis: C, 45.57; H, 4.67; N, 29.52; O, 20.23

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 Weeks
250mg USD 550.00 2 Weeks
1g USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
L-Biopterin; 6-Biopterin; NSC 339699; NSC-339699; NSC339699; AR 1D8544; AR-1D8544; AR1D8544; LS126316; LS-126316; LS 126316; tetrahybiopterin
IUPAC/Chemical Name
2-amino-6-((1S,2R)-1,2-dihydroxypropyl)pteridin-4(1H)-one
InChi Key
LHQIJBMDNUYRAM-AWFVSMACSA-N
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-/m1/s1
SMILES Code
O=C1N=C(N)NC2=NC=C([C@H](O)[C@H](O)C)N=C12
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 237.21 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Guibal P, Lévêque N, Doummar D, Giraud N, Roze E, Rodriguez D, Couderc R, Billette De Villemeur T, Moussa F. Simultaneous determination of all forms of biopterin and neopterin in cerebrospinal fluid. ACS Chem Neurosci. 2014 Jul 16;5(7):533-41. doi: 10.1021/cn4001928. Epub 2014 Apr 8. PubMed PMID: 24650440; PubMed Central PMCID: PMC4102970. 2: Lifshits M, Kovalerchik D, Carmeli S. Microcystbiopterins A-E, five O-methylated biopterin glycosides from two Microcystis spp. bloom biomasses. Phytochemistry. 2016 Mar;123:69-74. doi: 10.1016/j.phytochem.2016.01.010. Epub 2016 Jan 21. PubMed PMID: 26804212. 3: Kim HL, Kim DH, Lee YK, Park SO, Lee YW, Kwon OS, Park YS. An enzymatic method to distinguish tetrahydrobiopterin from oxidized biopterins using UDP-glucose:tetrahydrobiopterin glucosyltransferase. Anal Biochem. 2010 Feb 1;397(1):79-83. doi: 10.1016/j.ab.2009.10.007. Epub 2009 Oct 9. PubMed PMID: 19819217. 4: Marsálek P, Svoboda M, Smutná M, Blahová J, Vecerek V. Neopterin and biopterin as biomarkers of immune system activation associated with castration in piglets. J Anim Sci. 2011 Jun;89(6):1758-62. doi: 10.2527/jas.2010-3157. Epub 2011 Feb 4. PubMed PMID: 21297064. 5: Ziegler I, Hültner L. Tetrahydro-6-biopterin is associated with tetrahydro-7-biopterin in primary murine mast cells. FEBS Lett. 1992 Jul 28;307(2):147-50. PubMed PMID: 1644167. 6: Longo N, Arnold GL, Pridjian G, Enns GM, Ficicioglu C, Parker S, Cohen-Pfeffer JL; Phenylketonuria Demographics, Outcomes and Safety Registry.. Long-term safety and efficacy of sapropterin: the PKUDOS registry experience. Mol Genet Metab. 2015 Apr;114(4):557-63. doi: 10.1016/j.ymgme.2015.02.003. Epub 2015 Feb 16. PubMed PMID: 25724073. 7: Duch DS, Bowers SW, Woolf JH, Nichol CA. Biopterin cofactor biosynthesis: GTP cyclohydrolase, neopterin and biopterin in tissues and body fluids of mammalian species. Life Sci. 1984 Oct 29;35(18):1895-901. PubMed PMID: 6492998. 8: Longo N. Disorders of biopterin metabolism. J Inherit Metab Dis. 2009 Jun;32(3):333-42. doi: 10.1007/s10545-009-1067-2. Epub 2009 Feb 9. Review. Erratum in: J Inherit Metab Dis. 2009 Jun;32(3):457. PubMed PMID: 19234759. 9: Bayat A, Møller LB, Lund AM. [Diagnostics and treatment of phenylketonuria]. Ugeskr Laeger. 2015 Feb 16;177(8). pii: V07140383. Review. Danish. PubMed PMID: 25697170. 10: Fink JK, Barton N, Cohen W, Lovenberg W, Burns RS, Hallett M. Dystonia with marked diurnal variation associated with biopterin deficiency. Neurology. 1988 May;38(5):707-11. PubMed PMID: 2452381. 11: Takeda J, Nakata R, Ueno H, Murakami A, Iseki M, Watanabe M. Possible involvement of a tetrahydrobiopterin in photoreception for UV-B-induced anthocyanin synthesis in carrot. Photochem Photobiol. 2014 Sep-Oct;90(5):1043-9. doi: 10.1111/php.12302. Epub 2014 Jul 16. PubMed PMID: 24943195. 12: Trefz F, Lichtenberger O, Blau N, Muntau AC, Feillet F, Bélanger-Quintana A, van Spronsen F, Munafo A. Tetrahydrobiopterin (BH4) responsiveness in neonates with hyperphenylalaninemia: a semi-mechanistically-based, nonlinear mixed-effect modeling. Mol Genet Metab. 2015 Apr;114(4):564-9. doi: 10.1016/j.ymgme.2015.01.013. Epub 2015 Feb 7. PubMed PMID: 25726095. 13: Fujishiro K, Hagihara M, Takahashi A, Nagatsu T. Concentrations of neopterin and biopterin in the cerebrospinal fluid of patients with Parkinson's disease. Biochem Med Metab Biol. 1990 Oct;44(2):97-100. PubMed PMID: 2252621. 14: Slazyk WE, Spierto FW. Liquid-chromatographic measurement of biopterin and neopterin in serum and urine. Clin Chem. 1990 Jul;36(7):1364-8. PubMed PMID: 2372953. 15: Garbutt JC, Duch DS, Nichol CA, Woolf JH. Urinary biopterin and neopterin excretion and pituitary-adrenal activity in psychiatric patients. Psychiatry Res. 1985 Nov;16(3):181-7. PubMed PMID: 4089052. 16: Duch DS, Woolf JH, Nichol CA, Davidson JR, Garbutt JC. Urinary excretion of biopterin and neopterin in psychiatric disorders. Psychiatry Res. 1984 Feb;11(2):83-9. PubMed PMID: 6584938. 17: Katoh S, Sueoka T, Matsuura S, Sugimoto T. Biopterin and neopterin in human saliva. Life Sci. 1989;45(26):2561-8. PubMed PMID: 2615555. 18: Nixon JC, Lee CL, Milstien S, Kaufman S, Bartholomé K. Neopterin and biopterin levels in patients with atypical forms of phenylketonuria. J Neurochem. 1980 Oct;35(4):898-904. PubMed PMID: 7452296. 19: Lindsay A, Healy J, Mills W, Lewis J, Gill N, Draper N, Gieseg SP. Impact-induced muscle damage and urinary pterins in professional rugby: 7,8-dihydroneopterin oxidation by myoglobin. Scand J Med Sci Sports. 2016 Mar;26(3):329-37. doi: 10.1111/sms.12436. Epub 2015 Mar 13. PubMed PMID: 25772829. 20: Shintaku H. [Biopterin and child neurologic disease]. No To Hattatsu. 2009 Jan;41(1):5-10. Review. Japanese. PubMed PMID: 19172809.