Nebularine
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| Category | Antibiotics |
| Catalog number | BBF-02595 |
| CAS | 550-33-4 |
| Molecular Weight | 252.23 |
| Molecular Formula | C10H12N4O4 |
| Purity | ≥ 95% by HPLC |
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Description
Nebularine is originally isolated from Agaricus nebularis. Shown to have inhibitory effects against mouse Sarcoma 180 and mycobacteria.
Specification
| Synonyms | Purine-9-ß-D-ribofuranoside; 9-β-D-Ribofuranosyl-9H-purine; Ribosyl-isopurine; N-D-Ribosylpurine; Purinosine; NSC 65423 |
| Storage | Store at -20°C |
| IUPAC Name | (2R,3S,4R,5R)-2-(hydroxymethyl)-5-purin-9-yloxolane-3,4-diol |
| Canonical SMILES | C1=C2C(=NC=N1)N(C=N2)C3C(C(C(O3)CO)O)O |
| InChI | InChI=1S/C10H12N4O4/c15-2-6-7(16)8(17)10(18-6)14-4-13-5-1-11-3-12-9(5)14/h1,3-4,6-8,10,15-17H,2H2/t6-,7-,8-,10-/m1/s1 |
| InChI Key | MRWXACSTFXYYMV-FDDDBJFASA-N |
Properties
| Appearance | Off-white to Beige Solid |
| Antibiotic Activity Spectrum | neoplastics (Tumor); mycobacteria |
| Boiling Point | 591.56°C at 760 mmHg |
| Melting Point | 180-181°C |
| Density | 1.92 g/cm3 |
| Solubility | Soluble in DMSO (Slightly), Ethanol, Methanol (Slightly) |
Reference Reading
1. Synthesis of Azido and Triazolyl Purine Ribonucleosides
Dāgs Dāvis Līpiņš, Andris Jeminejs, Irina Novosjolova, Ērika Bizdēna, Māris Turks Curr Protoc. 2021 Sep;1(9):e241. doi: 10.1002/cpz1.241.
Here, we describe detailed synthetic protocols for preparation of 6-amino/thio-2-triazolylpurine ribonucleosides. First, 9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2,6-diazido-9H-purine, to be used as a key starting material, is synthesized in an SN Ar reaction with NaN3 starting from commercially available 9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine. Next, 2,6-bis-triazolylpurine ribonucleoside is obtained in a CuAAC reaction between diazidopurine derivative and phenyl acetylene, and used in SN Ar reactions with N- and S-nucleophiles. In these reactions, the triazolyl ring at the purine C6 position acts as a good leaving group. Cleavage of acetyl protecting groups from the ribosyl moiety is achieved in presence of piperidine. In the SN Ar reaction with amino acid derivatives, the acetyl groups remain intact. Moreover, 9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2,6-diazido-9H-purine is selectively reduced at the C6 position using a CuSO4 ·5H2 O/sodium ascorbate system. This provides a straightforward approach for synthesis of 9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-6-amino-2-azido-9H-purine. © 2021 Wiley Periodicals LLC Basic Protocol 1: Synthesis of 6-amino-2-triazolylpurine ribonucleosides Basic Protocol 2: Synthesis of 6-thio-2-triazolylpurine ribonucleosides Basic Protocol 3: Synthesis of 6-amino-2-azidopurine ribonucleoside.
2. Synthesis of new nebularine analogues and their inhibitory activity against adenosine deaminase
Nikolaos Lougiakis, Panagiotis Marakos, Nicole Pouli, Elisabeth Fragopoulou, Roxane Tenta Chem Pharm Bull (Tokyo). 2015;63(2):134-42. doi: 10.1248/cpb.c14-00731.
A number of new 2,6-disubstituted-1-deazanebularine analogues as well as two structurally related pyrazole-fused tricyclic nucleosides were prepared. Their synthesis was carried out by the conversion of 6-amino-2-picoline to a suitable 1-deazapurine, followed by a Vorbrüggen type glycosylation and subsequent elaboration of the condensed pyrazole ring. The synthesized nebularine analogues proved to be weak adenosine deaminase inhibitors.
3. Nebularine (9-2'-deoxy-beta-D-ribofuranosylpurine) has the template characteristics of adenine in vivo and in vitro
M S Rahman, M Z Humayun Mutat Res. 1997 Jul 3;377(2):263-8. doi: 10.1016/s0027-5107(97)00084-5.
Nebularine (9-beta-D-ribofuranosylpurine; Nb) is a naturally occurring nucleoside with structural features suggestive of a universal base. However, previous observations based on thermal melting characteristics of oligonucleotides suggested that Nb formed stable pairs only with thymine. To determine the template characteristics of Nb, we constructed M13 viral single-stranded DNA (ssDNA) molecules bearing a single site-specific deoxynebularine (9-2'-deoxy-beta-D-ribofuranosylpurine) residue. The ssDNA constructs were transfected into Escherichia coli cells to determine the specificity of base insertion opposite Nb, as well as to determine the effect of Nb on the replicability of the transfected DNA. Base insertion opposite Nb, analyzed by a multiplex sequencing technology, suggests that Nb has the template characteristics of adenine. Analysis of DNA replicability, measured as transfection efficiency, indicates that Nb does not block DNA replication. UV irradiation of host cells before transfection did not significantly affect survival or base insertion specificity within the limits of multiplex sequencing technology employed, suggesting that inducible mutagenic phenomena appear to have only minor effects on translesion synthesis across Nb. In addition, in vitro DNA elongation experiments on oligonucleotide templates using E. coli DNA polymerase I (Klenow fragment) as the model polymerase showed that Nb templates for T, but not for other bases under the tested conditions. The data reported in this communication underscore the importance of base-pair geometry as a specificity-determinant during base insertion by replicative polymerases.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
