Tubercidin
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| Category | Antibiotics |
| Catalog number | BBF-03427 |
| CAS | 69-33-0 |
| Molecular Weight | 266.25 |
| Molecular Formula | C11H14N4O4 |
| Purity | ≥98% by HPLC |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-03427 | 500 mg | $439 | In stock |
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Add to cartDescription
Tubercidin is an adenosine analog with antiviral, antitrypanosomal, and antifungal properties. It inhibits DNA/RNA synthesis and other metabolic processes.
Specification
| Synonyms | 7-Deazaadenosine; Antibiotic XK 101-1; BRN 0038498; 4-Amino-7-(beta-D-ribofuranosyl)-pyrrolo(2,3-d)pyrimidine |
| Shelf Life | As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly |
| Storage | Store at-20°C |
| IUPAC Name | (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol |
| Canonical SMILES | C1=CN(C2=NC=NC(=C21)N)C3C(C(C(O3)CO)O)O |
| InChI | InChI=1S/C11H14N4O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2,(H2,12,13,14)/t6-,7-,8-,11-/m1/s1 |
| InChI Key | HDZZVAMISRMYHH-KCGFPETGSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White Crystalline Powder |
| Application | 7-Deaza-adenosine is an adenosine analog. |
| Antibiotic Activity Spectrum | neoplastics (Tumor); fungi |
| Boiling Point | 648.8°C at 760 mmHg |
| Melting Point | >209°C |
| Density | 1.9 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1.Synthesis of 7-Deaza-cyclic Adenosine-5'-diphosphate-carbocyclic-ribose and Its 7-Bromo Derivative as Intracellular Ca(2+)-Mobilizing Agents.
Takano S, Tsuzuki T, Murayama T1, Sakurai T1, Fukuda H, Arisawa M, Shuto S. J Org Chem. 2015 Jul 2;80(13):6619-27. doi: 10.1021/acs.joc.5b00723. Epub 2015 Jun 23.
Cyclic ADP-carbocyclic-ribose (cADPcR, 3) is a biologically and chemically stable equivalent of cyclic ADP-ribose (cADPR, 1), a Ca(2+)-mobilizing second messenger. We became interested in the biological activity of the 7-deaza analogues of cADPcR, i.e., 7-deaza-cADPcR (7) and its 7-bromo derivative, i.e., 7-deaza-7-Br-cADPcR (8), because 7-deazaadenosine is an efficient bioisostere of adenosine. The synthesis of 7 and 8 required us to construct the key N1-carbocyclic-ribosyl-7-deazaadenosine structure. Therefore, we developed a general method for preparing N1-substituted 7-deazaadenosines by condensing a 2,3-disubstituted pyrrole nucleoside with amines. Using this method, we prepared the N1-carbocyclic ribosyl 7-deazaadenosine derivative 10a, from which we then synthesized the target 7-deaza-cADPcR (7) via an Ag(+)-promoted intramolecular condensation to construct the 18-membered pyrophosphate ring structure. The corresponding 7-bromo derivative 8, which was the first analogue of cADPR with a substitution at the 7-position, was similarly synthesized.
2.Design and synthesis of fluorescent 7-deazaadenosine nucleosides containing π-extended diarylacetylene motifs.
De Ornellas S1, Slattery JM, Edkins RM, Beeby A, Baumann CG, Fairlamb IJ. Org Biomol Chem. 2015 Jan 7;13(1):68-72. doi: 10.1039/c4ob02081b.
C-modified 7-deazaadenosines containing a diphenylacetylene moiety have been synthesised using cross-coupling approaches. The C-modified nucleosides exhibit remarkable fluorescence properties, including high quantum yields. Solvatochromic studies show a near linear correlation between the Stokes shift and solvent polarity which is indicative of intramolecular charge transfer. DFT calculations have allowed us to correlate the experimentally observed photophysical properties with the calculated HOMO-LUMO energy gaps within a series of real and model compounds.
3.Molecular design of an environmentally sensitive fluorescent nucleoside, 3-deaza-2'-deoxyadenosine derivative: distinguishing thymine by probing the DNA minor groove.
Suzuki A1, Yanaba T, Saito I, Saito Y. Chembiochem. 2014 Jul 21;15(11):1638-44. doi: 10.1002/cbic.201402078. Epub 2014 Jul 8.
An environmentally sensitive fluorescent nucleoside containing a 3-deazaadenine skeleton has been developed, and its photophysical properties were investigated. Newly developed C3-naphthylethynylated 3-deaza-2'-deoxyadenosine ((3nz) A, 1) exhibited dual fluorescence emission from an intramolecular charge-transfer state and a locally excited state, depending upon molecular coplanarity. DNA probes containing 1 clearly discriminated a perfectly matched thymine base on the complementary strand by a distinct change in emission wavelength.
4.7-Cyclopropyl-2'-deoxytubercidin: a carbocyclic side-chain derivative of 7-deaza-2'-deoxyadenosine.
Yang H1, Budow-Busse S2, Eickmeier H3, Reuter H3, Seela F1. Acta Crystallogr C Struct Chem. 2014 Dec;70(Pt 12):1116-20. doi: 10.1107/S205322961402378X. Epub 2014 Nov 6.
The title compound {systematic name: 4-amino-5-cyclopropyl-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine}, C14H18N4O3, exhibits an anti glycosylic bond conformation, with the torsion angle χ = -108.7 (2)°. The furanose group shows a twisted C1'-exo sugar pucker (S-type), with P = 120.0 (2)° and τm = 40.4 (1)°. The orientation of the exocyclic C4'-C5' bond is -ap (trans), with the torsion angle γ = -167.1 (2)°. The cyclopropyl substituent points away from the nucleobase (anti orientation). Within the three-dimensional extended crystal structure, the individual molecules are stacked and arranged into layers, which are highly ordered and stabilized by hydrogen bonding. The O atom of the exocyclic 5'-hydroxy group of the sugar residue acts as an acceptor, forming a bifurcated hydrogen bond to the amino groups of two different neighbouring molecules. By this means, four neighbouring molecules form a rhomboidal arrangement of two bifurcated hydrogen bonds involving two amino groups and two O5' atoms of the sugar residues.
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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
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
