| Identification | Back Directory | [Name]
Amicetin-A | [CAS]
17650-86-1 | [Synonyms]
amicetin
Amicetin-A
Amomycin A
Benzamide, 4-[[(2S)-2-amino-3-hydroxy-2-methyl-1-oxopropyl]amino]-N-[1-[(2R,5S,6R)-5-[[4,6-dideoxy-4-(dimethylamino)-α-D-glucopyranosyl]oxy]tetrahydro-6-methyl-2H-pyran-2-yl]-1,2-dihydro-2-oxo-4-pyrimidinyl]- | [Molecular Formula]
C29H42N6O9 | [MDL Number]
MFCD01674585 | [MOL File]
17650-86-1.mol | [Molecular Weight]
618.68 |
| Chemical Properties | Back Directory | [Melting point ]
244-245° | [alpha ]
D24 +116.5° (c = 0.5 in 0.1N HCl) | [Boiling point ]
660.6°C (rough estimate) | [density ]
1.2721 (rough estimate) | [refractive index ]
1.6400 (estimate) | [pka]
pKa = 10.4, 7.0(at 25℃) |
| Hazard Information | Back Directory | [Uses]
Amicetin is a potent antibiotic. Amicetin shows antibiotic activities against gram-positive bacteria. Amicetin inhibits protein synthesis[1][2][3]. | [Enzyme inhibitor]
These pyrimidine-containing glycoside antibiotic (FWAmicetin-A = 617.69 g/mol (free base); CAS 17650-86-1; FWAmicetin-B = 532.59 g/mol (free base)) from Streptomyces vinaceus-drappus and S. fasciculatus inhibits protein biosynthesis, exerting its bacteriostatic most potently on Grampositive bacteria. Amicetin B, also called plicacetin, was isolated from Streptomyces plicatus and has the identical structure minus the amethylseryl residue. It is weaker in action compared to amicetin A. Target(s): peptidyltransferase; peptidyl-tRNA hydrolase, or aminoacyl-tRNA hydrolase; ribonuclease P; protein biosynthesis. | [References]
[1] HINUMA Y, et al. An amicetin (sacromycin) from Streptomyces sp. No. 5223. Studies on Streptomyces antibiotics. XXXVI. J Antibiot (Tokyo). 1955 Nov;8(5):148-52. PMID:13306673
[2] Fu, J., et al. Total Synthesis of Nucleoside Antibiotics Amicetin, Plicacetin, and Cytosaminomycin A—D. Chinese Journal of Chemistry, 2021, 39(10), 2679-2684.
[3] Ennis, H. L. et, al. Polysome Metabolism in Escherichia coli: Amicetin, an Antibiotic That Stabilizes Polysomes. Antimicrobial Agents and Chemotherapy, 1972, 1(3), 204-209. doi:10.1128/aac.1.3.204. DOI:10.1128/AAC.1.3.204 |
| Safety Data | Back Directory | [Toxicity]
LD50 of citrate complex, pH 6 (mg/kg) in mice: ~90 i.v., 600-700 s.c.; in rats: ~200 i.v., ~600 s.c. (DeBoer) |
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