Streptothricin group antibiotic

In contrast to the streptomycin-neomycin group of antibiotics, the members of the streptothricin group are not composed solely of carbohydrate moieties. In addition to the 2-amino-2-deoxy-D-guIose, the molecules contain one or more units of the unusual amino acid 3,6-diamino-hexanoic acid (jS-lysine) (10) together with a heterocyclic guanidine... 

Antibiotics of the streptothricine group are unstable in acid and especially in alkali. Their salts with mineral acids are insoluble in organic solvents, their IR spectra are identical, and the melting points of their salts are very similar (65KPS42). 

The streptolidine lactam (1), a component of the streptothricin group of antibiotics, has been synthesized as outlined in Scheme 1 o-Glucose has been used as an optically active source material for the synthesis of a-multistriatin (2), a beetle hormone, which is summarized in Scheme 2, and of (- )-c/j-rose oxide (3), shown in Scheme 3. ... 

Streptolidine (473), a guanidinoamino-acid that occurs as a component of the streptothricin group of antibiotics, has been synthesized by way of the lactam form (472) of (2S, 35,4i )-2,3,5-triamino-4-hydroxypentanoic acid (Scheme 154) 936 2R, 35, 45)-4-Amino-3-hydroxy-2-methyl-5-(pyrid-3-yl)pentanoic acid (474), a component of the antibiotic pyridomycin, has been derived from 3-deoxy-l,2 5,6-di-0-isopropylidene-3-C-methyl-a-D-allofuranose by the sequence of reactions outlined in Scheme 155. ... 

A group of soil actinomycete Streptomyces nojiriertsis have been identified as producing derivatives of streptothricin antibiotics of the general structure (654) which incorporates a hexahydro imidazo[4,5-c]pyridine system into the molecule <87JAN1140>. The total synthesis of streptothricin F has been reported <82TL296i>. 

Cyanogen bromide ring closure of (417) was used to prepare streptolidine lactam (418), a guanidine-containing amino acid lactam moiety of the streptothricin antibiotic group (77BCJ2375), that moiety being a 4,5,6,7-tetrahydroimidazo[4,5-c]pyridine. 

Some strains of Streptomyces are able to produce a series of antibiotics of similar activity they are designated streptothricines (StTs) (54JA566). Six substances with a similar behaviour were separated from different antibiotics of streptothridne group and were indexed as A-Fourth varying repeating units. The structure and properties of these antibiotics were extensively studied. 

Three years later the discovery of a second chemotherapeutic antibiotic, streptomycin, was reported by Schatz, Bugie and Waksman . Streptomycin was encountered in the course of a search for antibiotics among the acti-nomycetes. Members of this group of micro-organisms had been the subject of extensive study by Waksman and his colleagues. One of them had previously yielded the antibiotic streptothricin, which was too toxic to be clinically useful. 

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