Deepoxidation of 16-membered epoxyenone macrolide antibiotics. I. Microbial deepoxidation and subsequent isomerization of deltamycins A1, A2, A3, A4 (carbomycin A) and X.

FUKAGAWA YASUO, MUTOH YOSHIFUMI, ISHIKURA TOMOYUKI, LEIN JOSEPH

doi:10.7164/antibiotics.37.118

Deepoxidation of 16-membered epoxyenone macrolide antibiotics. I. Microbial deepoxidation and subsequent isomerization of deltamycins A1, A2, A3, A4 (carbomycin A) and X.

DOI PubMed

FUKAGAWA YASUO

Sanraku-Ocean Co., Ltd., Central Research Laboratories
MUTOH YOSHIFUMI

Sanraku-Ocean Co., Ltd., Central Research Laboratories
ISHIKURA TOMOYUKI

Sanraku-Ocean Co., Ltd., Central Research Laboratories
LEIN JOSEPH

Panlabs, Inc.

書誌事項

タイトル別名

I. MICROBIAL DEEPOXIDATION AND SUBSEQUENT ISOMERIZATION OF DELTAMYCINS A1, A2, A3, A4 (CARBOMYCIN A) AND X

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説明

Carbomycin A (deltamycin A₄) was deepoxidized to carbomycin A P1 by Streptomyces halstedii subsp. deltae (a deltamycins producer), favorably under anaerobic conditions. Carbomycin A P1 was spontaneously converted to geometric isomers designated carbomycins A P2 and A P3. This type of deepoxidation and subsequent isomerization was not limited to carbomycin A, but generally occurrable in other 16-membered epoxyenone macrolide compounds. Many bacteria and actinomycetes were also found to have an ability to deepoxidize deltamycins reductively. The chemical structures of carbomycins A P1, A P2 and A P3 were elucidated as shown in Fig. 3.