Issue 6, 2006
From the journal:

Organic & Biomolecular Chemistry

Aggregation modes in sheets formed by protected β-amino acids and β-peptides

Anindita Sengupta,a   Rituparna S. Roy,b   Varatharajan Sabareesh,b   Narayanaswamy Shamala*a  and  Padmanabhan Balaram*b  

* Corresponding authors

a Department of Physics, Indian Institute of Science, Bangalore, India
E-mail: shamala@physics.iisc.ernet.in
Fax: +91 80 23602602/+91 80 23600683

b Molecular Biophysics Unit, Indian Institute of Science, Bangalore, India
E-mail: pb@mbu.iisc.ernet.in
Fax: +91 80 23600683/+91 80 23600535

Abstract

The crystal structures of four protected β-amino acid residues, Boc-(S)-β3-HAla-NHMe (1); Boc-(R)-β3-HVal-NHMe (2); Boc-(S)-β3-HPhe-NHMe (3); Boc-(S)-β3-HPro-OH (6) and two β-dipeptides, Boc-(R)-β3-HVal-(R)-β3-HVal-OMe (4); Boc-(R)-β3-HVal-(S)-β3-HVal-OMe (5) have been determined. Gauche conformations about the Cβ–Cα bonds (θ ∼ ±60°) are observed for the β3-HPhe residues in 3 and all four β3-HVal residues in the dipeptides 4 and 5. Trans conformations (θ ∼ 180°) are observed for β3-HAla residues in both independent molecules in 1 and for the β3-HVal and β3-HPro residues in 2 and 6, respectively. In the cases of compounds 1–5, molecules associate in the crystals via intermolecular backbone hydrogen bonds leading to the formation of sheets. The polar strands formed by β3-residues aggregate in both parallel (1, 3, 5) and antiparallel (2, 4) fashion. Sheet formation accommodates both the trans and gauche conformations about the Cβ–Cα bonds.

Graphical abstract: Aggregation modes in sheets formed by protected β-amino acids and β-peptides

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Article information

DOI
https://doi.org/10.1039/B516088J
Article type
Paper
Submitted
14 Nov 2005
Accepted
13 Jan 2006
First published
30 Jan 2006

Org. Biomol. Chem., 2006,4, 1166-1173

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Aggregation modes in sheets formed by protected β-amino acids and β-peptides

A. Sengupta, R. S. Roy, V. Sabareesh, N. Shamala and P. Balaram, Org. Biomol. Chem., 2006, 4, 1166 DOI: 10.1039/B516088J

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