Alkoxyamino glycoside acceptors for the regioselective synthesis of oligosaccharides using glycosynthases and transglycosidases

Bioorganic & Medicinal Chemistry Letters
David TezeCharles Tellier

Abstract

Alkoxyamino derivatives of oligosaccharides have been synthesized by enzymatic synthesis using a glycosynthase and a transglycosidase. The chemoselective assembly of unprotected oligosaccharides bearing glucose at the reducing end with N-alkyl-O-benzylhydroxylamine provides sugar derivatives that are good acceptors for enzymatic synthesis using either glycosynthase or transglycosidase. Furthermore, this method affords the possibility of controlling the regioselectivity of coupling depending on the nature of the alkoxyamino substituent and provides high-yield coupling of sugars without the need for complex protecting group chemistry.

References

Sep 5, 2002·Chembiochem : a European Journal of Chemical Biology·Jon K FairweatherAntoni Planas

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Citations

Nov 30, 2013·Protein Engineering, Design & Selection : PEDS·David TezeMichel Dion
Jan 10, 2017·Chembiochem : a European Journal of Chemical Biology·Klaus VilladsenMikkel B Thygesen
Nov 2, 2016·Organic & Biomolecular Chemistry·N Chen, J Xie
May 31, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Birgitte ZeunerAnne S Meyer
Oct 25, 2016·Chemistry : a European Journal·Oliver R BaudendistelValentin Wittmann
Nov 18, 2020·The Journal of Organic Chemistry·Christophe DussouyCyrille Grandjean
Mar 8, 2018·Organic Letters·Tommi ÖsterlundPasi Virta
Jan 4, 2017·Organic Letters·Mohammed K Abd El-GaberChisato Mukai

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