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B2517

Sigma-Aldrich

6-Biopterin

≥97%

Sinónimos:

(1’R,2’S)-Biopterin, 2-Amino-4-hydroxy-6-(1,2-dihydroxypropyl)pteridine, L-erythro-6-(1,2-Dihydroxypropyl)pterin

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About This Item

Fórmula empírica (notación de Hill):
C9H11N5O3
Número de CAS:
22150-76-1
Peso molecular:
237.22
Beilstein/REAXYS Number:
87860
EC Number:
244-807-8
MDL number:
MFCD00036787
UNSPSC Code:
41106305
PubChem Substance ID:
24891654
NACRES:
NA.51

assay

≥97%

form

powder

storage temp.

2-8°C

SMILES string

C[C@H](O)[C@H](O)c1cnc2NC(N)=NC(=O)c2n1

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

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Application

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Siew Ling Choy et al.
Scientific reports, 7(1), 9472-9472 (2017-08-27)
Intracellular pathogens belonging to the genus Leishmania have developed effective strategies that enable them to survive within host immune cells. Immunostimulatory compounds that counteract such immunological escape mechanisms represent promising treatment options for diseases. Here, we demonstrate that a lipopeptidephosphoglycan
Adrien Weingärtner et al.
PloS one, 7(8), e42070-e42070 (2012-08-08)
The protozoan parasite Leishmania is an intracellular pathogen infecting and replicating inside vertebrate host macrophages. A recent model suggests that promastigote and amastigote forms of the parasite mimic mammalian apoptotic cells by exposing phosphatidylserine (PS) at the cell surface to
Sanjeewa Gamagedara et al.
Clinica chimica acta; international journal of clinical chemistry, 412(1-2), 120-128 (2010-09-28)
Biomarkers are good potential tools for early cancer diagnosis. Here we have analyzed eight different pteridines in the urine samples of cancer patients and compared them with samples from healthy subjects. Pteridines are important cofactors in the process of cell
Abulizi Abudukadier et al.
Diabetes, 62(9), 3033-3043 (2013-05-08)
Endothelial nitric oxide synthase (eNOS) dysfunction induces insulin resistance and glucose intolerance. Tetrahydrobiopterin (BH4) is an essential cofactor of eNOS that regulates eNOS activity. In the diabetic state, BH4 is oxidized to 7,8-dihydrobiopterin, which leads to eNOS dysfunction owing to
Jarl Underhaug et al.
Current topics in medicinal chemistry, 12(22), 2534-2545 (2013-01-24)
Phenylketonuria (PKU) is a loss-of-function inborn error of metabolism. As many other inherited diseases the main pathologic mechanism in PKU is an enhanced tendency of the mutant phenylalanine hydroxylase (PAH) to misfold and undergo ubiquitin-dependent degradation. Recent alternative approaches with
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