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Phleomycin

Phleomycin is a glycopeptide antibiotic that binds DNA but does not intercalate. Phleomycin is mutagenic and requires metal ions to induce double-stranded DNA breaks. This compound displays some antibacterial and antifungal activities.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18953674

Cas No.

11006-33-0

Purity

≥97%

Formula

C51H75N17O21S2

Formula Wt.

1326.38

IUPAC Name

2-[2-[2-[[2-[[4-[[2-[[6-amino-2-[3-amino-1-[(2,3-diamino-3-oxopropyl)amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[(2R,3S,4S,5S,6S)-3-[(2S,3R,4R,5S)-4-carbamoyl-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)-3-methyloxan-2-yl]oxy-3-(1H-imidazol-5-yl)propanoyl]amino]-3-hydroxy-2-methylpentanoyl]amino]-3-oxobutanoyl]amino]ethyl]-4,5-dihydro-1,3-thiazol-4-yl]-1,3-thiazole-4-carboxamide

Synonym

NSC 61586; NSC 616586.

Solubility

Soluble in water (10mg/mL); slightly sol in methanol.

Appearance

Blue powder

van Peer AF, de Bekker C, Vinck A, et al. Phleomycin increases transformation efficiency and promotes single integrations in Schizophyllum commune. Appl Environ Microbiol. 2009 Mar;75(5):1243-7. PMID: 19114524.

Povirk LF, Hogan M, Dattagupta N, et al. Copper(II).bleomycin, iron(III).bleomycin, and copper(II).phleomycin: comparative study of deoxyribonucleic acid binding. Biochemistry. 1981 Feb 3;20(3):665-71. PMID: 6163448.

Sleigh MJ. The mechanism of DNA breakage by phleomycin in vitro. Nucleic Acids Res. 1976 Apr;3(4):891-901. PMID: 818624.

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