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Two Diastereomeric Artificial Enzymes with Different Catalytic Activity
Author(s) -
Lindbäck Emil,
Zhou You,
Pedersen Christian Marcus,
Bols Mikael
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200699
Subject(s) - chemistry , diastereomer , hydrogen peroxide , aldehyde , dihydroxylation , catalysis , aryl , hydrolysis , cyclodextrin , organic chemistry , alcohol , biocatalysis , glycoside , enantioselective synthesis , reaction mechanism , alkyl
Two epimeric cyclodextrin‐6‐ C ‐aldehydes were synthesised in 10 steps from β‐cyclodextrin. The synthesis involved protection/partial deprotection, oxidation to a 6‐aldehyde, olefination, dihydroxylation, selective protection of the secondary alcohol and oxidation. The two isomers catalysed theoxidation of aromatic amines by hydrogen peroxide but predominantly outside the cavity. Hydrolysis of aryl glycosides on the other hand was catalysed in a reaction followingMichaelis–Menten kinetics. The S isomer was a 5–20 times better catalyst than the R isomer, which was explained from models.