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New preorganized ?-amino acids as foldamer building blocks.

ABSTRACT: An asymmetric synthesis of two new diastereomeric ?-amino acids is described. Both molecules contain a cyclohexyl ring to limit conformational flexibility about the C?-C? bond; they differ in having cis vs trans stereochemistry on the ring. Residues derived from the cis ? isomer are shown to support helical secondary structures in ?/?-peptide oligomers.

SUBMITTER: Guo L 

PROVIDER: S-EPMC3445736 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature

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New preorganized γ-amino acids as foldamer building blocks.

Guo Li L   Zhang Weicheng W   Guzei Ilia A IA   Spencer Lara C LC   Gellman Samuel H SH  

Organic letters 20120508 10

An asymmetric synthesis of two new diastereomeric γ-amino acids is described. Both molecules contain a cyclohexyl ring to limit conformational flexibility about the Cα-Cβ bond; they differ in having cis vs trans stereochemistry on the ring. Residues derived from the cis γ isomer are shown to support helical secondary structures in α/γ-peptide oligomers. ...[more]

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