Bamicetin
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| Category | Antibiotics |
| Catalog number | BBF-00265 |
| CAS | 43043-14-7 |
| Molecular Weight | 604.65 |
| Molecular Formula | C28H40N6O9 |
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Description
Bamicetin is produced by the strain of Streptomyces licatus. Mainly resistant to gram-positive bacteria and Mycobacteria, acute toxicity is lower than Amicetin (dog, subcutaneous).
Specification
| Synonyms | Benzamide, 4-((2-amino-3-hydroxy-2-methyl-1-oxopropyl)amino)-N-(1,2-dihydro-2-oxo-1-(2,3,6-trideoxy-4-O-(4,6-dideoxy-4-(methylamino)-alpha-D-glucopyranosyl)-beta-D-erythro-hexopyranosyl)-4-pyrimidinyl)-, (S)- |
| IUPAC Name | 4-[(2-amino-3-hydroxy-2-methylpropanoyl)amino]-N-[1-[5-[3,4-dihydroxy-6-methyl-5-(methylamino)oxan-2-yl]oxy-6-methyloxan-2-yl]-2-oxopyrimidin-5-yl]benzamide |
| Canonical SMILES | CC1C(CCC(O1)N2C=C(C=NC2=O)NC(=O)C3=CC=C(C=C3)NC(=O)C(C)(CO)N)OC4C(C(C(C(O4)C)NC)O)O |
| InChI | InChI=1S/C28H40N6O9/c1-14-19(43-25-23(37)22(36)21(30-4)15(2)42-25)9-10-20(41-14)34-12-18(11-31-27(34)40)32-24(38)16-5-7-17(8-6-16)33-26(39)28(3,29)13-35/h5-8,11-12,14-15,19-23,25,30,35-37H,9-10,13,29H2,1-4H3,(H,32,38)(H,33,39) |
| InChI Key | RYBQPRIRVSUQBG-UHFFFAOYSA-N |
Properties
| Appearance | Colorless Crystallineline |
| Antibiotic Activity Spectrum | gram-positive bacteria; mycobacteria |
| Melting Point | 240-241 °C |
| Solubility | Soluble in methanol, hot ethanol. |
Reference Reading
1. 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.
2. Inhibition of translation in bacterial and eukaryotic systems by the antibiotic anthelmycin (hikizimycin)
A González, D Vázquez, A Jiménez Biochim Biophys Acta. 1979 Feb 27;561(2):403-9. doi: 10.1016/0005-2787(79)90148-5.
Anthelmycin inhibits protein synthesis on both pro- and eukaryotic ribosomes by preventing the peptide bond-forming reaction. The drug is structurally similar to certain other 4-aminohexosyl cytosine antibiotics including blasticidin S, gougerotin, amicetin and bamicetin although unlike these compounds anthelmycin lacks an aminoacyl moiety. It is proposed that anthelmycin inhibits the ribosomal peptidyl transferase centre by associating with a site that overlaps the (related) ribosomal receptor site(s) for the other four inhibitors.
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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 ╳
