Microbial conversion of milbemycins: hydroxylation of milbemycin A4 and related compounds by Cunninghamella echinulata ATCC 9244.
Many strains of zygomycetes and actinomycetes were found to convert milbemycin A4 (1a) to 13 beta-hydroxymilbemycin A4 (1b). Among these strains, Cunninghamella echinulata ATCC 9244 had the most efficient 13 beta-hydroxylation ability on milbemycins. In the conversion of milbemycin A3 (2a), 29-hydroxymilbemycin A4 (4a), and 30-hydroxymilbemycin A4 (5a) with this strain, only 13 beta-hydroxylated products were obtained. On the other hand, starting from milbemycin A4 (1a) and 5-ketomilbemycin A4 5-oxime (6a), 13 beta,24- and 13 beta,30-dihydroxy derivatives were also isolated along with 13 beta-hydroxylated products. Similarly, conversion of milbemycin D (3a) and LL-F28249 alpha (8a) gave 13 beta- and 28-hydroxy derivatives (8b and 8c).
Nakagawa
K
K
Fermentation Research Laboratories, Sankyo Co., Ltd., Tokyo, Japan.
Miyakoshi
S
S
Torikata
A
A
Sato
K
K
Tsukamoto
Y
Y
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D006900:Hydroxylation; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009090:Mucorales / Q000378:metabolism*; D013055:Spectrophotometry, Infrared
D000900:Anti-Bacterial Agents; D018942:Macrolides; C027837:moxidectin