Herbicidin B
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| Category | Antibiotics |
| Catalog number | BBF-01342 |
| CAS | 55353-32-7 |
| Molecular Weight | 453.40 |
| Molecular Formula | C18H23N5O9 |
| Purity | >95% |
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Description
It is produced by the strain of Streptomyces saganoensis. It has herbicidal and anti-gram-positive bacterial activity.
Specification
| Synonyms | Herbicidine B; 9-(6,10-Anhydro-5-deoxy-11-methyl-2-O-methylundec-7-ulopyranosefuranosyluronosyl)-9H-purin-6-amine; (11R)-11-C-(6-Amino-9H-purin-9-yl)-2,6:8,11-dianhydro-10-O-methyl-7-deoxy-α-L-ido-D-lyxo-5-undecoulo-5,9-pyranosonic acid methyl ester |
| IUPAC Name | methyl (1S,3S,4R,5R,7R,9R,11S,12S,13S)-5-(6-aminopurin-9-yl)-1,12,13-trihydroxy-4-methoxy-2,6,10-trioxatricyclo[7.4.0.03,7]tridecane-11-carboxylate |
| Canonical SMILES | COC1C2C(CC3C(O2)(C(C(C(O3)C(=O)OC)O)O)O)OC1N4C=NC5=C(N=CN=C54)N |
| InChI | InChI=1S/C18H23N5O9/c1-28-12-10-6(30-16(12)23-5-22-8-14(19)20-4-21-15(8)23)3-7-18(27,32-10)13(25)9(24)11(31-7)17(26)29-2/h4-7,9-13,16,24-25,27H,3H2,1-2H3,(H2,19,20,21)/t6-,7-,9-,10+,11+,12-,13+,16-,18-/m1/s1 |
| InChI Key | GZBSICLBZYSADI-DHNWSQMASA-N |
Properties
| Appearance | White Acicular Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 746.6±70.0 °C (Predicted) |
| Melting Point | 155 °C (dec.) |
| Density | 2.00±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol |
Reference Reading
1. Herbicidin congeners, undecose nucleosides from an organic extract of Streptomyces sp. L-9-10
Xingyun Chai, Ui Joung Youn, Dianqing Sun, Jingqiu Dai, Philip Williams, Tamara P Kondratyuk, Robert P Borris, Julian Davies, Ivan G Villanueva, John M Pezzuto, Leng Chee Chang J Nat Prod. 2014 Feb 28;77(2):227-33. doi: 10.1021/np4006635. Epub 2014 Feb 17.
Four new undecose nucleosides (herbicidin congeners), three known herbicidins, and 9-(β-d-arabinofuranosyl)hypoxanthine (Ara-H) were isolated from the organic extract of a fermentation culture of Streptomyces sp. L-9-10 using proton NMR-guided fractionation. Their structures were elucidated on the basis of comprehensive 1D and 2D NMR and mass spectrometry analyses. These structures included 2'-O-demethylherbicidin F (1), 9'-deoxy-8',8'-dihydroxyherbicidin B (2), 9'-deoxy-8'-oxoherbicidin B (2a), and the 8'-epimer of herbicidin B (3). This is the first detailed assignment of proton and carbon chemical shifts for herbicidins A, B, and F. The isolated compounds were evaluated for cancer chemopreventive potential based on inhibition of tumor necrosis factor alpha (TNF-α)-induced nuclear factor-kappa B (NF-κB) activity.
2. Fine synthetic nucleoside chemistry based on nucleoside natural products synthesis
Satoshi Ichikawa Chem Pharm Bull (Tokyo). 2008 Aug;56(8):1059-72. doi: 10.1248/cpb.56.1059.
Synthetic nucleoside chemistry based on nucleoside natural products synthesis were described. First, a samarium diiodide (SmI 2)-promoted aldol reaction with the use of alpha-phenylthioketone as an enolate was developed. The characteristics of this reaction are that the enolate can be regioselectively generated and the aldol reaction proceeds under near neutral condition. This reaction is proved to be a powerful reaction for the synthesis of complex nucleoside natural products, and herbicidin B and fully protected tunicaminyluracil, which were undecose nucleoside natural products, were synthesized. Next, the synthetic methodology of the caprazamycins, which are promising antibacterial nucleoside natural products, was also developed by the strategy including beta-selective ribosylation without using a neighboring group participation. Our synthetic route provided a range of key analogues with partial structures to define the pharmacophore. Simplification of the caprazamycins was further pursued to develop diketopiperazine analogs.
3. [Synthetic study of nucleoside antibiotics]
Satoshi Ichikawa Yakugaku Zasshi. 2006 Aug;126(8):579-95. doi: 10.1248/yakushi.126.579.
Some of nucleoside antibiotics include complex structures as well as sensitive functionality, which are challenging targets for organic chemists. Among complex nucleoside antibiotics, there are also good drug candidates because they possess a variety of interesting biological properties. Herbicidin B and fully protected tunicaminyluracil, which were undecose nucleoside antibiotics, were synthesized using a samarium diiodide (SmI(2)) mediated aldol reaction with the use of alpha-phenylthioketones as enolate sources. The characteristics of the SmI(2)-mediated aldol reaction are that the enolate can be regioselectively generated and the aldol reaction proceeds under near neutral condition. This reaction is proved to be a powerful reaction for the synthesis of complex nucleoside antibiotics. The synthesis of caprazol, the core structure of caprazamycins, was conducted by the strategy including beta-selective ribosylation without using a neighboring group participation and the construction of a diazepanone by a modified reductive amination. Our synthetic route would provide a range of key analogues with partial structures to define the pharmacophore, which can be a lead for the development of more effective anti-bacterial agents.
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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 ╳
