Chemical transformation of seldomycin 5 into 3'-episeldomycin 5 and its antibacterial activity.

概要

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3′-Episeldomycin 5 (7) was synthesized from seldomycin 5. Reaction of hexa-N-ethoxycarbonylseldomycin 5 (2) with o-nitrobenzenesulfonyl chloride gave penta-N-ethoxycarbonylseldomycin 5-2′,3′-epicyclic carbamate (3) in one step. Hexa-N-ethoxycarbonyl-3′-O-tosylseldomycin 5 or hexa-N-ethoxycarbonyl-3′-O-mesylseldomycin 5, prepared from 2, was also converted into 3 by being heated in weakly basic solvents such as N,N-dimethylformamide or pyridine. Compound 3 was hydrolyzed to give 7. Structure of 7 was confirmed by PMR, CMR, MS, and Δ[M] values. Compound 7 was found to be active against resistant bacteria which carry 3′-O-phosphorylating enzymes. Δ[M] values for vicinal amino groups were shortly discussed.
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