Feglymycin, a novel inhibitor of the replication of the human immunodeficiency virus. Fermentation, isolation and structure elucidation.
The novel peptide feglymycin has been isolated from cultures of Streptomyces sp. DSM 11171 by solid phase extraction, size exclusion chromatography and repeated reversed-phase chromatography. The molecular weight was found to be 1900.90 g/mol and the molecular formula is C95H97Nl3O30. Feglymycin contains 13 amino acids of which four are 3-hydroxyphenylglycine and five are 3,5-dihydroxyphenylglycine residues. The structure of the linear peptide has been determined by 1H and 13C NMR spectroscopy. The sequence was confirmed by the observed mass spectroscopic fragmentation pattern. As well as having weak antibacterial activity, feglymycin inhibits the replication of the human immunodeficiency virus (HIV) in vitro.
Hoechst Marion Roussel Deutschland GmbH, Drug Innovation & Approval, Frankfurt, Germany.
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Vértesy
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Aretz
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Knauf
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Markus
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Vogel
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Wink
D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002850:Chromatography, Gel; D004926:Escherichia coli / Q000187:drug effects; D005285:Fermentation; D008401:Gas Chromatography-Mass Spectrometry; D015726:Giant Cells / Q000187:drug effects; D006678:HIV / Q000187:drug effects* / Q000502:physiology; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008970:Molecular Weight; D010455:Peptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011506:Proteins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects; D013212:Staphylococcus epidermidis / Q000187:drug effects; D013297:Streptococcus pyogenes / Q000187:drug effects; D013302:Streptomyces / Q000737:chemistry* / Q000378:metabolism; D014779:Virus Replication / Q000187:drug effects*
D000998:Antiviral Agents; D010455:Peptides; D011506:Proteins; C120179:feglymycin