Issue 23, 2011

Design and synthesis of trans-3-aminopyran-2-carboxylic acid (APyC) and α/β-peptides with 9/11-helix

Abstract

A new β-amino acid, trans-3-aminopyran-2-carboxylic acid (APyC), was designed and synthesized from (R)-glyceraldehyde derivative and used in the synthesis of α/β-peptides in a 1 : 1 alternating pattern with D-Ala. The presence of oxygen atom at the Cβ2-position in APyC was envisaged to provide opportunity for additional interaction. These hybrid peptides have shown the presence of 9/11-helix through extensive NMR and MD studies. The amide protons of D-Ala, in addition to participating in 9-mr H-bonding with CO of succeeding β-residue, were also involved in additional electrostatic interaction with pyran ring oxygen of preceding β-residue, which facilitated further stabilization to the 9/11-mixed helix. The study thus results in a new ‘motif’ for a 9/11-helix, and the first example from a cyclic β-amino acid.

Graphical abstract: Design and synthesis of trans-3-aminopyran-2-carboxylic acid (APyC) and α/β-peptides with 9/11-helix

Supplementary files

Article information

Article type
Paper
Submitted
28 Jul 2011
Accepted
01 Sep 2011
First published
19 Oct 2011

Org. Biomol. Chem., 2011,9, 8102-8111

Design and synthesis of trans-3-aminopyran-2-carboxylic acid (APyC) and α/β-peptides with 9/11-helix

G. V. M. Sharma, K. S. Reddy, S. J. Basha, K. R. Reddy and A. V. S. Sarma, Org. Biomol. Chem., 2011, 9, 8102 DOI: 10.1039/C1OB06279D

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