Carbazomycin B
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| Category | Antibiotics |
| Catalog number | BBF-00222 |
| CAS | 75139-38-7 |
| Molecular Weight | 241.28 |
| Molecular Formula | C15H15NO2 |
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Description
Carbazomycin B is a nitrogen-containing heterocyclic antibiotic produced by streptomyces H-1051-MY 10. It can inhibit a variety of plant pathogenic fungi, and has weak anti-bacterial and anti-yeast activity.
Specification
| Synonyms | 1,2-Dimethyl-3-methoxy-9H-carbazol-4-ol |
| IUPAC Name | 3-methoxy-1,2-dimethyl-9H-carbazol-4-ol |
| Canonical SMILES | CC1=C(C(=C(C2=C1NC3=CC=CC=C32)O)OC)C |
| InChI | InChI=1S/C15H15NO2/c1-8-9(2)15(18-3)14(17)12-10-6-4-5-7-11(10)16-13(8)12/h4-7,16-17H,1-3H3 |
| InChI Key | OBMFXFPFPDTBHG-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
Reference Reading
1. New antibiotics, carbazomycins A and B. III. Taxonomy and biosynthesis
K Ishimaru, M Kaneda, S Nakamura, Y Ueki, R Nomi, K Yamasaki, K Watanabe, N Yoshida, T Nakajima J Antibiot (Tokyo) . 1983 May;36(5):552-8. doi: 10.7164/antibiotics.36.552.
The carbazomycin-producing microorganism, strain H 1051-MY 10, was determined to a strain of Streptoverticillium ehimense. Biosynthesis of carbazomycin B was studied using 14C-labeled and 13C-enriched precursors in combination with 13C NMR spectroscopy. The C-2 carbon of [2-13C]trytophan was shown to be involved at the C-3 carbon in carbazomycin B and both carbons of [1,2-13C]acetate at the C-1 and C-10 moiety of the antibiotic. [CH3-13C]Methionine was involved at the methoxyl group but not at the methyl group on the C-2 carbon of the antibiotic. Neither of the labeled carbons, [1-14C]tryptophan nor [2,3-13C]propionic acid, was detected in the antibiotic, and a progenitor of the C-2 and C-11 moiety of the antibiotic has not been determined.
2. Short Syntheses of 4-Deoxycarbazomycin B, Sorazolon E, and (+)-Sorazolon E2
Hiroaki Sasai, Kazuya Ichinose, Shinobu Takizawa, Makoto Sako Chem Asian J . 2017 Jun 19;12(12):1305-1308. doi: 10.1002/asia.201700471.
Short syntheses of 4-deoxycarbazomycin B and sorazolon E were established through the condensation of cyclohexanone and commercially available 4-methoxy-2,3-dimethylaniline, followed by PdII-catalyzed dehydrogenative aromatization/intramolecular C-C bond coupling and deprotection. A chiral dinuclear vanadium complex (Ra,S,S)-6 mediated the enantioselective oxidative coupling of sorazolon E, affording (+)-sorazolon E2 in good enantioselectivity.
3. Diversity oriented convergent access for collective total synthesis of bioactive multifunctional carbazole alkaloids: synthesis of carbazomycin A, carbazomycin B, hyellazole, chlorohyellazole, and clausenaline D
Shivaji B Markad, Narshinha P Argade Org Lett . 2014 Oct 17;16(20):5470-3. doi: 10.1021/ol502721r.
Facile syntheses of imperative carbazole alkaloids carbazomycin A, carbazomycin B, hyellazole, chlorohyellazole, and clausenaline D have been demonstrated starting from readily available Boc-protected 3-formylindole and dimethyl maleate. The suitably substituted aromatic rings have been designed comprising three/four significant C-C bond forming reactions. The competent Wittig reaction, selective monoalkylations, one-pot regioselective Weinreb amide formation and Boc-deprotection, well designed Grignard reactions, dehydrative intramolecular cyclizations, and Baeyer-Villiger rearrangement of aromatic aldehydes were the main features.
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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 ╳
