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Extending the Scope of GTFR Glucosylation Reactions with Tosylated Substrates for Rare Sugars Synthesis
Author(s) -
Görl Julian,
Possiel Christian,
Sotriffer Christoph,
Seibel Jürgen
Publication year - 2017
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201700320
Subject(s) - regioselectivity , chemistry , isomaltose , stereochemistry , biocatalysis , organic chemistry , maltose , catalysis , enzyme , reaction mechanism
Functionalized rare sugars were synthesized with 2‐, 3‐, and 6‐tosylated glucose derivatives as acceptor substrates by transglucosylation with sucrose and the glucansucrase GTFR from Streptococcus oralis . The 2‐ and 3‐tosylated glucose derivatives yielded the corresponding 1,6‐linked disaccharides (isomaltose analogues), whereas the 6‐tosylated glucose derivatives resulted in 1,3‐linked disaccharides (nigerose analogue) with high regioselectivity in up to 95 % yield. Docking studies provided insight into the binding mode of the acceptors and suggested two different orientations that were responsible for the change in regioselectivity.