Avidinorubicin
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| Category | Antibiotics |
| Catalog number | BBF-00232 |
| CAS | |
| Molecular Weight | 1215.34 |
| Molecular Formula | C60H86N4O22 |
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Description
Avidinorubicin is produced by the strain of Streptomyces avidinii. It has anti-gram positive and negative bacterial activity, and has cytotoxicity to tumor cells.
Specification
| IUPAC Name | 4-[(2S,3R,4S,6S)-6-[(2S,3R,4R,6R)-4-amino-6-[(2S,3R,4R,6R)-4-amino-6-[[23-(dimethylamino)-10-[(2R,4S,5S,6S)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy-8,12,15,22-tetrahydroxy-1,12-dimethyl-6,17-dioxo-20,25-dioxahexacyclo[19.3.1.02,19.05,18.07,16.09,14]pentacosa-2(19),3,5(18),7,9(14),15-hexaen-24-yl]oxy]-2,4-dimethyloxan-3-yl]oxy-2,4-dimethyloxan-3-yl]oxy-4-methoxy-2-methyloxan-3-yl]oxy-4-oxobutanoic acid |
| Canonical SMILES | CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C=CC6=C5OC7C(C(C(C6(O7)C)OC8CC(C(C(O8)C)OC9CC(C(C(O9)C)OC1CC(C(C(O1)C)OC(=O)CCC(=O)O)OC)(C)N)(C)N)N(C)C)O)O)(C)O)N(C)C)O |
| InChI | InChI=1S/C60H86N4O22/c1-24-45(68)31(63(9)10)18-36(76-24)80-33-21-57(5,74)20-29-40(33)48(71)42-43(47(29)70)49(72)41-28(46(42)69)14-15-30-52(41)85-56-50(73)44(64(11)12)55(60(30,8)86-56)84-39-23-59(7,62)54(27(4)79-39)83-38-22-58(6,61)53(26(3)78-38)82-37-19-32(75-13)51(25(2)77-37)81-35(67)17-16-34(65)66/h14-15,24-27,31-33,36-39,44-45,50-51,53-56,68,70-71,73-74H,16-23,61-62H2,1-13H3,(H,65,66)/t24-,25-,26-,27-,31-,32-,33?,36-,37-,38+,39+,44?,45+,50?,51+,53-,54-,55?,56?,57?,58+,59+,60?/m0/s1 |
| InChI Key | XMRHMVSZMLOUMS-VKSYZSCISA-N |
Properties
| Appearance | Red Powder |
| Antibiotic Activity Spectrum | gram-positive bacterial; gram-negative bacteria; neoplastics (Tumor) |
| Melting Point | 206-209 °C |
Reference Reading
1. Hydrogen-Bonding-Assisted Exogenous Nucleophilic Reagent Effect for β-Selective Glycosylation of Rare 3-Amino Sugars
Jing Zeng, Ruobin Wang, Shuxin Zhang, Jing Fang, Shanshan Liu, Guangfei Sun, Bingbing Xu, Ying Xiao, Dengxian Fu, Wenqi Zhang, Yixin Hu, Qian Wan J Am Chem Soc. 2019 May 29;141(21):8509-8515. doi: 10.1021/jacs.9b01862. Epub 2019 May 15.
Challenges for stereoselective glycosylation of deoxy sugars are notorious in carbohydrate chemistry. We herein report a novel strategy for the construction of the less investigated β-glycosidic bonds of 3,5- trans-3-amino-2,3,6-trideoxy sugars (3,5- trans-3-ADSs), which constitute the core structure of several biologically important antibiotics. Current protocol leverages a C-3 axial sulfonamide group in 3,5- trans-3-ADSs as a hydrogen-bond (H-bond) donor and repurposes substoichiometric phosphine oxide as an exogenous nucleophilic reagent (exNu) to establish an intramolecular H-bond between the former and the derived α-oxyphosphonium ion. This pivotal interaction stabilizes the α-face-covered intermediate to inhibit the formation of the more reactive β-intermediate, thereby yielding reversed β-selectivity, which is unconventional for an exNu-mediated glycosylation system. A wide range of substrates was accommodated, and good to excellent β-selectivities were ensured by this H-bonding-assisted exNu effect. The robustness of the current strategy was further attested by the architectural modification of natural products and drugs containing 3,5- trans-3-ADSs, as well as the synthesis of a trisaccharide unit in avidinorubicin.
2. Structural studies on avidinorubicin, a novel anthracycline with platelet aggregation inhibitory activity
M Aoki, H Shirai, N Nakayama, Y Itezono, M Mori, T Satoh, S Ohshima, J Watanabe, K Yokose, H Seto J Antibiot (Tokyo). 1991 Jun;44(6):635-45. doi: 10.7164/antibiotics.44.635.
Avidinorubicin (MW 1,214, C60H86N4O22) was isolated from the cultured broth of strain NR0576 (which was identified as Streptomyces avidinii Stapley et al.) by butyl alcohol extraction, Sephadex LH-20 column chromatography and preparative HPLC. Avidinorubicin inhibited thrombin-induced platelet aggregation with an IC50 being 7.9 microM and was determined to be a novel anthracycline possessing two units of a new aminosugar, avidinosamine, in place of two decilonitrose groups in decilorubicin.
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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 ╳
