Identification of a cyclase gene dictating the C-9 stereochemistry of anthracyclines from Streptomyces nogalater.
Nogalamycin is an anthracycline antibiotic produced by Streptomyces nogalater. Its aglycone has a unique stereochemistry (7S, 9S, 10R) compared to that of most other anthracyclines (7S, 9R, 10R). The gene snoaL, encoding a nogalonic acid methyl ester cyclase for nogalamycin, was used to generate nogalamycinone, demonstrating that the single cyclase dictates the C-9 stereochemistry of anthracyclines.
Torkkell
S
S
Department of Biochemistry, University of Turku, FIN-20014 Turku, Finland.
Kunnari
T
T
Palmu
K
K
Hakala
J
J
Mäntsälä
P
P
Ylihonko
K
K
D000595:Amino Acid Sequence; D000903:Antibiotics, Antineoplastic / Q000096:biosynthesis* / Q000737:chemistry; D001426:Bacterial Proteins; D003001:Cloning, Molecular; D003470:Culture Media; D004271:DNA, Fungal / Q000032:analysis; D005656:Fungal Proteins / Q000235:genetics / Q000302:isolation & purification / Q000378:metabolism; D007535:Isomerases / Q000096:biosynthesis / Q000235:genetics* / Q000378:metabolism; D008969:Molecular Sequence Data; D009621:Nogalamycin / Q000096:biosynthesis* / Q000737:chemistry; D017386:Sequence Homology, Amino Acid; D013237:Stereoisomerism; D013302:Streptomyces / Q000201:enzymology / Q000235:genetics* / Q000378:metabolism
D000903:Antibiotics, Antineoplastic; D001426:Bacterial Proteins; D003470:Culture Media; D004271:DNA, Fungal; D005656:Fungal Proteins; D007535:Isomerases; C405498:nogalonic acid methyl ester cyclase; D009621:Nogalamycin