Studies on Chemical Modification of Streptothricin-group Antibiotics. I. : On Citromycin Derivatives (Organic)

Citromycin (I) is converted into inactive citromycinic acid (II) by treatment with 3N hydrochloric acid and toxicity of II was less than one-half of that of I. Deformiminocitromycin (III) obtained by treatment with methanolic ammonia and deformiminocitromycin N-acetate (V) obtained by treatment with...

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Published inYAKUGAKU ZASSHI Vol. 92; no. 2; pp. 182 - 186
Main Authors TANIYAMA, HYOZO, SAWADA, YOSUKE, HASIMOTO, KEIZO
Format Journal Article
LanguageEnglish
Japanese
Published Japan The Pharmaceutical Society of Japan 01.02.1972
Subjects
Bacteria - drug effects
Benzopyrans - pharmacology
Chemical Phenomena
Chemistry
Fungi - drug effects
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Summary:Citromycin (I) is converted into inactive citromycinic acid (II) by treatment with 3N hydrochloric acid and toxicity of II was less than one-half of that of I. Deformiminocitromycin (III) obtained by treatment with methanolic ammonia and deformiminocitromycin N-acetate (V) obtained by treatment with N-acetoxysuccinimide no longer had the original antibacterial activity. These facts indicate that antibacterial activity of citromycin requires the partial structure of (i) formation of a lactam ring in the streptolidine moiety and (ii) protection of the terminal amino group in glycine by a basic group like formimino, and that deformimination and N-acetylation results in the loss of its antibacterial activity.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0031-6903
1347-5231
DOI:10.1248/yakushi1947.92.2_182