Two diastereomeric artificial enzymes with different catalytic activity

TY - JOUR

T1 - Two diastereomeric artificial enzymes with different catalytic activity

AU - Lindbäck, Emil Anders

AU - Zhou, You

AU - Pedersen, Christian Marcus

AU - Bols, Mikael

PY - 2012/9

Y1 - 2012/9

N2 - 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.

AB - 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.

U2 - 10.1002/ejoc.201200699

DO - 10.1002/ejoc.201200699

M3 - Journal article

SN - 1434-193X

VL - 2012

SP - 5366

EP - 5372

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 27

ER -