title: Microbial transformation of 6-O-methylerythromycin derivatives.
abstract: Mucor circinelloides f. griseo-cyanus IFO 4563 was found to convert 6-O-methylerythromycin A (TE-031, A-56268) to (14R)-14-hydroxy-6-O-methylerythromycin A [14R)-14-hydroxy TE-031). The TLC and spectral data of the conversion product were perfectly identical with those of an active major metabolite of TE-031 in humans (M-5). A related antibiotic, 6-O-methylerythromycin B (TB-010), was able to be similarly transformed to its C-14 hydroxy analogue [14R)-14-hydroxy-6-O-methylerythromycin B, (14R)-14-hydroxy TB-010). The MICs of (14R)-14-hydroxy-6-O-methylerythromycin B against some Gram-positive bacteria were almost equal to those of 6-O-methylerythromycin B. It is suggested that the hydroxylation at C-14 of 6-O-methylerythromycins A and B scarcely reduces their in vitro activity.
authors.affiliation: Research Center, Taisho Pharmaceutical Co., Ltd., Saitama, Japan.
authors.forename: J
authors.initials: J
authors.lastname: Sasaki
authors.forename: K
authors.initials: K
authors.lastname: Mizoue
authors.forename: S
authors.initials: S
authors.lastname: Morimoto
authors.forename: T
authors.initials: T
authors.lastname: Adachi
authors.forename: S
authors.initials: S
authors.lastname: Omura
mesh_terms: D055598:Chemical Phenomena; D002621:Chemistry; D017291:Clarithromycin; D004917:Erythromycin / Q000031:analogs & derivatives* / Q000378:metabolism; D006900:Hydroxylation; D008968:Molecular Conformation; D009089:Mucor / Q000378:metabolism*
chemical_list: D004917:Erythromycin; D017291:Clarithromycin