Cover Picture: Application of Biocatalysis to on‐DNA Carbohydrate Library Synthesis (ChemBioChem 9/2017). (26th April 2017)

• Record Type: Journal Article
• Authors: Thomas, Baptiste; Lu, Xiaojie; Birmingham, William R.; Huang, Kun; Both, Peter; Reyes Martinez, Juana Elizabeth; Young, Robert J.; Davie, Christopher P.; Flitsch, Sabine L.
• Is Part Of: Chembiochem. Volume 18:Number 9(2017)
• Page Start: 825
• Page End: 825
• Publication Date: 2017-04-26
• Subjects: biocatalysis -- biotransformation -- carbohydrate -- DNA-encoded libraries -- glycoconjugate; Biochemistry -- Periodicals; Molecular biology -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1002/cbic.201700179
• Languages: English
• ISSNs: 1439-4227

Abstract

Abstract : The cover picture shows how DNA‐encoded libraries are becoming more widely employed by the academic, biotechnology and pharmaceutical communities for hit identification and target validation. Although significant progress has been made in expanding the toolkit of on‐DNA compatible reactions, numerous synthetic transformations are still needed to increase the chemical space covered by DNA‐encoded libraries. Biocatalysis is particularly advantageous in this area as it is highly selective and can be performed in aqueous environments. We have demonstrated that, after installing the first carbohydrate building block onto DNA by chemical methods, the glycan structure could be elongated by using several glycosyltransferase additions. Furthermore, we used GOase to introduce aldehydes by site‐specific oxidation of the sugar substrates. The aldehyde functionality was then further functionalized either by hydrazone/oxime condensation or reductive amination. Overall, we have demonstrated the application of biocatalysis for the on‐DNA synthesis of carbohydrate‐based libraries by using enzymatic oxidation and glycosylation in combination with traditional organic chemistry. More information can be found in the communication by X. Lu, S. L. Flitsch et al. onpage 858 in Issue 9, 2017 (DOI:10.1002/cbic.201600678 ).