Diastereoselective amplification of an induced-fit receptor from a dynamic combinatorial library.
A high-affinity, induced-fit receptor for NMe4I was discovered using dynamic combinatorial chemistry. The addition of the guest to a dynamic combinatorial library made using a racemic mixture of chiral building blocks caused the strong and highly diastereoselective amplification of the receptor at the expense of other library components. The receptor and its mode of binding were characterized by NMR, ITC, and re-equilibration experiments, from which it was deduced that the receptor probably forms a folded four-stave barrel shape on binding of the guest.
Corbett
Peter T
PT
Cambridge University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK.
Tong
Lok H
LH
Sanders
Jeremy K M
JK
Otto
Sijbren
S
D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003500:Cyclization; D004220:Disulfides / Q000138:chemical synthesis / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013816:Thermodynamics
D004220:Disulfides; D006571:Heterocyclic Compounds; D047028:Macrocyclic Compounds