Aminopolyols from Carbohydrates: Amination of Sugars and Sugar‐Derived Tetrahydrofurans with Transaminases

Abstract

Scheme 1. Previous approach to sugar-derived THFsfrom sugars (e.g., 2a). This work using:a)T Ams to generate amine-THFs(e.g. 3a). b) TAms to generate acyclic aminopolyols.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.org/10.

Biocatalytic cascades towards iminosugar scaffolds reveals promiscuous activity of shikimate dehydrogenases

“…Applying biocatalytic retrosynthesis, we proposed an enzymatic cascade for the conversion of sugar aminopolyols, readily available through recently reported transamination methods 15,16 or chemical synthesis 17 (Scheme 1), into iminosugars via primary alcohol oxidation and imine reduction without the need of protection steps. This route was particularly attractive to us owing to the recent success of a similar methodology used to access 3-aminopiperidines and azepanes.…”

Regioselective Dehydration of Sugar Thioacetals under Mild Conditions

“…There have been recent reports on selective transformations of unprotected sugars and their derivatives using both biocatalytic 5,6,7,8 and chemical approaches 9,10,11 . De-oxygenation/dehydration of sugars is of particular interest and only a few approaches have been described.…”

Regioselective Dehydration of Sugar Thioacetals under Mild Conditions

“…There have been recent reports of selective transformations of unprotected sugars and their derivatives using both biocatalytic 5 − 8 and chemical approaches. 9 − 11 Deoxygenation/dehydration of sugars is of particular interest, and only a few approaches have been described.…”