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Cover Picture: Application of Biocatalysis to on‐DNA Carbohydrate Library Synthesis (ChemBioChem 9/2017)
Author(s) -
Thomas Baptiste,
Lu Xiaojie,
Birmingham William R.,
Huang Kun,
Both Peter,
Reyes Martinez Juana Elizabeth,
Young Robert J.,
Davie Christopher P.,
Flitsch Sabine L.
Publication year - 2017
Publication title -
chembiochem
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201700179
Subject(s) - biocatalysis , reductive amination , hydrazone , chemistry , combinatorial chemistry , click chemistry , glycome , dna , oxime , glycan , organic chemistry , biochemistry , reaction mechanism , glycoprotein , catalysis
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. on page 858 in Issue 9, 2017 (DOI: 10.1002/cbic.201600678).