Amicetin B
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| Category | Antibiotics |
| Catalog number | BBF-00434 |
| CAS | 43043-15-8 |
| Molecular Weight | 517.57 |
| Molecular Formula | C25H35N5O7 |
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Description
It is produced by the strain of Streptomuces sp. R-285. The antibacterial activity was lower than that of Amicetin.
Specification
| Synonyms | Plicacetin; Benzamide, 4-amino-N-(1-(5-((4,6-dideoxy-4-(dimethylamino)-alpha-D-glucopyranosyl)oxy)tetrahydro-6-methyl-2H-pyran-2-yl)-1,2-dihydro-2-oxo-4-pyrimidinyl)-, (2R-(2-alpha,5-beta,6-alpha))-; DTXSID70962868; 4-amino-N-[1-[5-[5-(dimethylamino)-3,4-dihydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]-2-oxopyrimidin-4-yl]benzamide |
| IUPAC Name | 4-amino-N-[1-[5-[5-(dimethylamino)-3,4-dihydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]-2-oxopyrimidin-4-yl]benzamide |
| Canonical SMILES | CC1C(CCC(O1)N2C=CC(=NC2=O)NC(=O)C3=CC=C(C=C3)N)OC4C(C(C(C(O4)C)N(C)C)O)O |
| InChI | InChI=1S/C25H35N5O7/c1-13-17(37-24-22(32)21(31)20(29(3)4)14(2)36-24)9-10-19(35-13)30-12-11-18(28-25(30)34)27-23(33)15-5-7-16(26)8-6-15/h5-8,11-14,17,19-22,24,31-32H,9-10,26H2,1-4H3,(H,27,28,33,34) |
| InChI Key | NFOMJDXALJABQF-UHFFFAOYSA-N |
Properties
| Appearance | White Crystals |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria |
| Melting Point | 165-167 °C |
| Solubility | Soluble in Methanol, Hydrochloric acid, Sodium hydroxide |
Reference Reading
1. Mining Indonesian Microbial Biodiversity for Novel Natural Compounds by a Combined Genome Mining and Molecular Networking Approach
Ira Handayani, Hamada Saad, Shanti Ratnakomala, Puspita Lisdiyanti, Wien Kusharyoto, Janina Krause, Andreas Kulik, Wolfgang Wohlleben, Saefuddin Aziz, Harald Gross, Athina Gavriilidou, Nadine Ziemert, Yvonne Mast Mar Drugs. 2021 May 28;19(6):316. doi: 10.3390/md19060316.
Indonesia is one of the most biodiverse countries in the world and a promising resource for novel natural compound producers. Actinomycetes produce about two thirds of all clinically used antibiotics. Thus, exploiting Indonesia's microbial diversity for actinomycetes may lead to the discovery of novel antibiotics. A total of 422 actinomycete strains were isolated from three different unique areas in Indonesia and tested for their antimicrobial activity. Nine potent bioactive strains were prioritized for further drug screening approaches. The nine strains were cultivated in different solid and liquid media, and a combination of genome mining analysis and mass spectrometry (MS)-based molecular networking was employed to identify potential novel compounds. By correlating secondary metabolite gene cluster data with MS-based molecular networking results, we identified several gene cluster-encoded biosynthetic products from the nine strains, including naphthyridinomycin, amicetin, echinomycin, tirandamycin, antimycin, and desferrioxamine B. Moreover, 16 putative ion clusters and numerous gene clusters were detected that could not be associated with any known compound, indicating that the strains can produce novel secondary metabolites. Our results demonstrate that sampling of actinomycetes from unique and biodiversity-rich habitats, such as Indonesia, along with a combination of gene cluster networking and molecular networking approaches, accelerates natural product identification.
2. Parallel induction strategies for cat-86: separating chloramphenicol induction from protein synthesis inhibition
E J Rogers, N P Ambulos Jr, Z Gu, P S Lovett Mol Microbiol. 1993 Jun;8(6):1063-9. doi: 10.1111/j.1365-2958.1993.tb01651.x.
Induction of cat-86 translation results from the stalling of a ribosome at a discrete location in the leader region of the transcript. Stalling destabilizes an adjacent region of secondary structure that sequesters the cat-86 ribosome binding site, thereby activating cat-86 translation. Two well characterized antibiotics, chloramphenicol and erythromycin, induce cat-86 by stalling a ribosome at the appropriate leader site. Here we demonstrate differences between the two antibiotics with respect to induction. First, induction by chloramphenicol is dependent on nucleotides in the leader sequence that are different from those necessary for erythromycin induction. Second, variants of Bacillus subtilis that are chloramphenicol resistant because of chromosome mutations permit cat-86 induction by chloramphenicol, whereas erythromycin-resistance host mutations block or greatly reduce cat-86 induction by erythromycin. Third, selected strains of B. subtilis bearing alterations in proteins of the 50S ribosomal subunit interfere with cat-86 induction by chloramphenicol, yet these strains are chloramphenicol sensitive. Lastly, induction by chloramphenicol is not reversed by removal of the antibiotic whereas erythromycin induction is reversible. The data indicate that chloramphenicol induction results from an effect of the drug that is not identical to its role as a general inhibitor of ribosome elongation. Induction by erythromycin, on the other hand, could not be distinguished from its antibiotic activity.
3. Anti-mycobacterial nucleoside antibiotics from a marine-derived Streptomyces sp. TPU1236A
Ying-Yue Bu, Hiroyuki Yamazaki, Kazuyo Ukai, Michio Namikoshi Mar Drugs. 2014 Dec 17;12(12):6102-12. doi: 10.3390/md12126102.
Five new nucleoside antibiotics, named streptcytosines A-E (1-5), and six known compounds, de-amosaminyl-cytosamine (6), plicacetin (7), bamicetin (8), amicetin (9), collismycin B (10), and SF2738 C (11), were isolated from a culture broth of Streptomyces sp. TPU1236A collected in Okinawa, Japan. The structures of new compounds were elucidated on the basis of their spectroscopic data (HRFABMS, IR, UV, and 2D NMR experiments including 1H-1H COSY, HMQC, HMBC, and NOESY spectra). Streptcytosine A (1) belonged to the amicetin group antibiotics, and streptcytosines B-E (2-5) were derivatives of de-amosaminyl-cytosamine (6), 2,3,6-trideoxyglucopyranosyl cytosine. Compound 1 inhibited the growth of Mycobacterium smegmatis (MIC = 32 µg/mL), while compounds 2-5 were not active at 50 µg/disc. Bamicetin (8) and amicetin (9) showed the MICs of 16 and 8 µg/mL, respectively.
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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 ╳
