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Disaccharide Mimetics by Enzymatic Tandem Aldol Additions
Author(s) -
Eyrisch Oliver,
Fessner WolfDieter
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199516391
Subject(s) - chemistry , aldolase a , disaccharide , aldol reaction , stereocenter , dihydroxyacetone phosphate , biocatalysis , dihydroxyacetone , enzyme catalysis , tandem , stereochemistry , combinatorial chemistry , fructose bisphosphate aldolase , organic chemistry , catalysis , enzyme , reaction mechanism , enantioselective synthesis , materials science , composite material , glycerol
Tail‐to‐tail C,C ‐coupled pyranoses or furanoses like 2 with a disaccharide‐like structure were obtained from hydroxylated dialdehydes like 1 under aldolase catalysis. The key step is the twofold addition of dihydroxyacetone phosphate. As many as six stereocenters in the products can be controlled by a thermodynamically selective reaction mode.
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