scholarly journals Structure elucidation of colibactin and its DNA cross-links

Science ◽  
2019 ◽  
Vol 365 (6457) ◽  
pp. eaax2685 ◽  
Author(s):  
Mengzhao Xue ◽  
Chung Sub Kim ◽  
Alan R. Healy ◽  
Kevin M. Wernke ◽  
Zhixun Wang ◽  
...  
Keyword(s):  
Colorectal Cancer ◽  
Mass Spectrometry ◽  
Cell Biology ◽  
Structure Elucidation ◽  
Isotope Labeling ◽  
Tandem Mass ◽  
Physiological Effects ◽  
Human Gut ◽  
Structural Assignment ◽  
Cross Links

Colibactin is a complex secondary metabolite produced by some genotoxic gut Escherichia coli strains. The presence of colibactin-producing bacteria correlates with the frequency and severity of colorectal cancer in humans. However, because colibactin has not been isolated or structurally characterized, studying the physiological effects of colibactin-producing bacteria in the human gut has been difficult. We used a combination of genetics, isotope labeling, tandem mass spectrometry, and chemical synthesis to deduce the structure of colibactin. Our structural assignment accounts for all known biosynthetic and cell biology data and suggests roles for the final unaccounted enzymes in the colibactin gene cluster.

scholarly journals Structure elucidation of colibactin

2019 ◽  
Author(s):  
Mengzhao Xue ◽  
Chung Sub Kim ◽  
Alan R. Healy ◽  
Kevin M. Wernke ◽  
Zhixun Wang ◽  
...  
Keyword(s):  
Colorectal Cancer ◽  
Structure Prediction ◽  
Structure Elucidation ◽  
Isotope Labeling ◽  
Degradation Products ◽  
Cross Linking ◽  
Tandem Ms ◽  
Cross Link ◽  
Structural Assignment ◽  
Unknown Structure

AbstractColibactin is a gut microbiome metabolite of unknown structure that has been implicated in colorectal cancer formation. Several studies now suggest that the tumorgenicity of colibactin derives from interstrand cross-linking of host DNA. Here we use a combination of genetics, isotope labeling, tandem MS, and chemical synthesis to deduce the structure of colibactin. Our structural assignment accounts for all known biosynthetic data and suggests roles for the final unaccounted enzymes in the colibactin gene cluster. DNA cross-link degradation products derived from synthetic and natural colibactin were indistinguishable by tandem MS analysis, thereby confirming the structure prediction. This work reveals the structure of colibactin, which has remained incompletely defined for over a decade.

Ion trap multiple-stage tandem mass spectrometry as a pre-NMR tool in the structure elucidation of saponins

2000 ◽  
Vol 11 (3) ◽  
pp. 190-198 ◽  
Author(s):  
Dirk C van Setten ◽  
Gijsbert Zomer ◽  
Gerrit van de Werken ◽  
Emmanuel J H J Wiertz ◽  
Bas R Leeflang ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Tandem Mass Spectrometry ◽  
Structure Elucidation ◽  
Ion Trap ◽  
Tandem Mass

scholarly journals Gas-Phase Fragmentation of Cyclic Oligosaccharides in Tandem Mass Spectrometry

Molecules ◽  
2019 ◽  
Vol 24 (12) ◽  
pp. 2226 ◽  
Author(s):  
Alexander O. Chizhov ◽  
Yury E. Tsvetkov ◽  
Nikolay E. Nifantiev
Keyword(s):  
Mass Spectrometry ◽  
Tandem Mass Spectrometry ◽  
Gas Phase ◽  
Structure Elucidation ◽  
Mass Spectra ◽  
Food Additives ◽  
Tandem Mass ◽  
Modern Mass ◽  
Gas Phase Fragmentation ◽  
Different Sources

Modern mass spectrometry, including electrospray and MALDI, is applied for analysis and structure elucidation of carbohydrates. Cyclic oligosaccharides isolated from different sources (bacteria and plants) have been known for decades and some of them (cyclodextrins and their derivatives) are widely used in drug design, as food additives, in the construction of nanomaterials, etc. The peculiarities of the first- and second-order mass spectra of cyclic oligosaccharides (natural, synthetic and their derivatives and modifications: cyclodextrins, cycloglucans, cyclofructans, cyclooligoglucosamines, etc.) are discussed in this minireview.

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