2009-64-5 Usage
Description
Neopterin is a pyrazino-pyrimidine compound derived from GTP that represents an intermediate product in the synthetic pathway of biopterin and is an essential cofactor in neurotransmitter synthesis. Neopterin is released from macrophages upon immune stimulation with interferon-γ from activated T cells. It is routinely used as a biochemical tool to screen for and monitor the progression of certain diseases accompanied by hyperimmune stimulation.
Chemical Properties
off-white to yellow solid
Uses
Different sources of media describe the Uses of 2009-64-5 differently. You can refer to the following data:
1. Precursor in the biosynthesis of Biopterin. First isolated from the pupae of bees.
2. D-(+)-Neopterin has been used as a NADPH oxidase inhibitor while assessing the ability of NADPH oxidases in breast cancer cells to produce reactive oxygen species (ROS). [NADPH= nicotinamide adenine dinucleotide phosphate]
General Description
D-(+)-Neopterin is a pteridine derivative, naturally found in Dictyostelium discoideum. It is found in significant amounts in the urine of cancer patients.
Biochem/physiol Actions
Pterin cofactor; precursor of BH4 (tetrahydrobiopterin).
Purification Methods
Purification is as for biopterin. Also purify it on a Dowex-1 x 8 (formate form) column and elute with 0.03M ammonium formate buffer pH 8.0 then pH 7.2. The fluorescent neopterin fraction is evaporated under reduced pressure, leaving neopterin and ammonium formate (the latter sublimes out at high vacuum) behind. Stir the residue for 24hours with EtOH, collect the solid and recrystallise it from H2O. [Viscontini et al. Helv Chim Acta 53 1202 1970, cf Wachter et al. Eds Neopterin W de Gruyter, Berlin 1992, ISBN 9783110117905, Beilstein 26 IV 4038.]
Check Digit Verification of cas no
The CAS Registry Mumber 2009-64-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,0,0 and 9 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 2009-64:
(6*2)+(5*0)+(4*0)+(3*9)+(2*6)+(1*4)=55
55 % 10 = 5
So 2009-64-5 is a valid CAS Registry Number.
InChI:InChI=1/C9H11N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h1,4,6,15-17H,2H2,(H3,10,11,13,14,18)/t4-,6?/m1/s1
2009-64-5Relevant articles and documents
Studies on biologically active pteridines. IV. Synthesis of several biopterin derivatives as an antigen in radioimmunoassay for biopterin
Sugimoto,Matsuura,Nagatsu
, p. 2344 - 2347 (1980)
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Efficient total syntheses of natural neopterin glycosides: Neopterin glucronide and solfapterin
Hanaya, Tadashi,Iwasaki, Katsuya,Saeki, Kaori,Hattori, Takafumi
, p. 390 - 409 (2019/05/21)
1,2-Di-O-acetyl-N2-(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl) ethyl]neopterin (11a) and its 1,2-di-O-benzoyl analog (11b) were prepared from neopterin in 5 steps, respectively. Glycosylation of 11a with methyl 2,3,4-tri-O-benzoylD-glucopyranosyluronate bromide (15b) in the presence of silver triflate afforded the corresponding 3'-O-(β-D-glucopyranosyl) neopterin derivative (18) in 64% yield. The similar treatment of 11b with 2-azido-3,4,6-tri-O-benzoyl-2-deoxy-a-D-glucopyranosyl bromide (21b) provided the corresponding 3'-O-(α-D-glucopyranosyl)neopterin derivative (23a) in 58% yield. The first syntheses of neopterin glucronide (5) and solfapterin (6) were achieved by successive removal of the protecting groups of 18 and 23a, respectively.
