3 新抗生物質Tuberactinomycinの構成アミノ酸γ-Hydroxy-β-lysineの構造

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A new antibiotic, tuberactinomycin(TUM), has been obtained from the broth filtrate of Streptomyces griseoverticillatus var. tuberacticus which was isolated from a soil sample collected at Ohito-cho, Shizuoka-ken. TUM is a basic peptide and effective against tubercular bacilli. TUM is composed of serine, α,β-diaminopropionic acid, and two unknown amino acids A and B. Hydrolysis of 2,4-dinitrophenylated TUM gave DNP-A compound which was absorbed at 1780cm^<-1> due to γ-lactone in IR spectrum. The amino acid A was found to be a basic γ-hydroxy amino acid of a molecular formula C_6H_<14>O_3N_2. Furthermore, carbobenzoxy A compound was isolated from carbobenzoxylated product of the hydrolyzate of TUM. From the results of elementary analysis, NMR, ORD etc. of A and its carbobenzoxylated derivative, it is now concluded that the structure of the new amino acid A should be assigned to threo-γ-hydroxy-L-β-lysine. When TUM was treated with conc. H_2SO_4, and then hydrolyzed partially, erythro-γ-hydroxy-L-β-lysine was obtained. The structure determination and stereochemistry of both isomers will be discussed in detail.
天然有機化合物討論会の論文
1969-09-01