Secondary Metabolites by Chemical Screening, 22. Gabosines, New Carba-sugars FromStreptomyces
| Autor: | Axel Zeeck, Peter Hammann, Ralf Thiericke, G. Bach, Sabine Breiding-Mack, Klaus Hütter, Hermann Uhr, Susanne Grabley, Joachim Wink |
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| Rok vydání: | 1993 |
| Předmět: |
chemistry.chemical_classification
Chemical transformation Ketone biology 010405 organic chemistry Stereochemistry Organic Chemistry Cyclohexanone 010402 general chemistry biology.organism_classification 01 natural sciences Streptomyces 0104 chemical sciences Chemical screening chemistry.chemical_compound chemistry Physical and Theoretical Chemistry Optical rotation Secondary metabolism Derivatization |
| Zdroj: | Liebigs Annalen der Chemie. 1993:241-250 |
| ISSN: | 1099-0690 0170-2041 |
| DOI: | 10.1002/jlac.199319930143 |
| Popis: | Chemical screening of different Streptomycetes strains resulted in the detection, isolation, and structure elucidation of a number of novel carba-sugars. The constitution of these secondary metabolites, named gabosines A to K (1 to 11), was deduced from spectroscopic data as well as chemical transformation reactions. The gabosines exhibit a basic C7 skeleton and can be characterized as hydroxylated branched cyclohexanone derivatives, which show structural similarities to carbohydrates deriving from secondary metabolism. The configuration fo the gabosines (absolute stereochemistry for 1, 4, 5, and 6; relative configuration for the remaining metabolites) was determined by derivatization with chiral acids (Helmchen's method), NMR spectral analysis, as well as by a comparison of optical rotation values with those of the already known gabosines B (2) and C (3). The new term “ketocarbasugars” is used to characterize a typical ketone containing subgroup of carba-sugars originating from microbial sources. The well available natural gabosines can be used as suitable chiral building blocks. |
| Databáze: | OpenAIRE |
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