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Gabosines L, N and O: New Carba‐Sugars from Streptomyces with DNA‐Binding Properties
Author(s) -
Tang YuanQing,
Maul Corinna,
Höfs Regina,
Sattler Isabel,
Grabley Susanne,
Feng XiaoZhang,
Zeeck Axel,
Thiericke Ralf
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200001)2000:1<149::aid-ejoc149>3.0.co;2-s
Subject(s) - chemistry , derivatization , stereochemistry , dna , streptomyces , thin layer chromatography , chromatography , mass spectrometry , biochemistry , bacteria , biology , genetics
In addition to the known gabosines A ( 4 ), B ( 5 ) and C ( 6 ), three new gabosines L ( 1 ), N ( 2 ) and O ( 3 ) were detected by chemical screening as secondary metabolites of Streptomyces (strains GT 041230, GT 051024 and S 1096). The constitutions of 1 , 2 and 3 were established by spectroscopic techniques and derivatization reactions. The absolute stereochemistry of 1 and 2 was determined by Helmchen's method and has been verified in the case of gabosine N ( 2 ) by X‐ray analysis. The DNA‐binding properties of the gabosines were investigated and analyzed by binding studies using a recently developed thin‐layer chromatography technique (bimolecular‐chemical screening).