The essential requirement for an oligomer to be included in the foldamer family is to possess a well defined, repetitive secondary structure, imparted by conformational restrictions of the monomeric unit. In this connection we described the preparation and the conformational analysis of pseudopeptides containing the 4-carboxy oxazolidin-2-one unit: these compounds contain a cyclic urethane moiety, so that by coupling it with a carboxylic acid derivative an imido-type function is obtained. This latter group is characterized by a nitrogen atom connected to an endocyclic and an exocyclic carbonyl which tend to adopt the trans conformation. As a consequence of this locally constrained disposition effect, these imide-type oligomers are forced to fold in an ordered conformation, that can lead, in the solid state to the formation of fibers or platelets.

Oxazolidin-2-ones Based Foldamers

TOMASINI, CLAUDIA
2009

Abstract

The essential requirement for an oligomer to be included in the foldamer family is to possess a well defined, repetitive secondary structure, imparted by conformational restrictions of the monomeric unit. In this connection we described the preparation and the conformational analysis of pseudopeptides containing the 4-carboxy oxazolidin-2-one unit: these compounds contain a cyclic urethane moiety, so that by coupling it with a carboxylic acid derivative an imido-type function is obtained. This latter group is characterized by a nitrogen atom connected to an endocyclic and an exocyclic carbonyl which tend to adopt the trans conformation. As a consequence of this locally constrained disposition effect, these imide-type oligomers are forced to fold in an ordered conformation, that can lead, in the solid state to the formation of fibers or platelets.
COST Action CM0803 meeting Foldamers: building blocks, structure and function
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Claudia Tomasini
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11585/94303
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