Deepoxidation of 16-membered epoxyenone macrolide antibiotics. I. Microbial deepoxidation and subsequent isomerization of deltamycins A1, A2, A3, A4 (carbomycin A) and X.
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.
D001419:Bacteria / Q000378:metabolism*; D055598:Chemical Phenomena; D002621:Chemistry; D004852:Epoxy Compounds / Q000378:metabolism*; D004988:Ethers, Cyclic / Q000378:metabolism*; D007933:Leucomycins / Q000378:metabolism*; D010100:Oxygen / Q000494:pharmacology; D013302:Streptomyces / Q000378:metabolism; D013696:Temperature
D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D007933:Leucomycins; D010100:Oxygen