Issue 19, 2005
From the journal:

Organic & Biomolecular Chemistry

The role of the disulfide bond in amyloid-like fibrillogenesis in a model peptide system

Apurba Kumar Das,a   Michael G. B. Drew,b   Debasish Haldara  and  Arindam Banerjee*a  

* Corresponding authors

a Department of Biological Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700 032, India
E-mail: bcab@mahendra.iacs.res.in
Fax: +91-33-2473-2805

b School of Chemistry, The University of Reading, Whiteknights, Reading, UK

Abstract

Three terminally protected short peptides Bis[Boc–D-Leu(1)–Cys(2)–OMe] 1, Bis[Boc–Leu(1)–Cys(2)–OMe] 2 and Bis[Boc–Val(1)–Cys(2)–OMe] 3 exhibit amyloid-like fibrillar morphology. Single crystal X-ray diffraction analysis of peptide 1 clearly demonstrates that it adopts an overall extended backbone molecular conformation that self-assembles to form an intermolecular hydrogen-bonded antiparallel supramolecular β-sheet structure in crystals. Scanning electron microscopic (SEM) images, transmission electron microscopic (TEM) images and Congo red binding studies vividly demonstrate the amyloid-like fibril formation of peptides 1, 2 and 3. However, after reduction of the disulfide bridge of peptides 1, 2 and 3, three newly generated peptides Boc–D-Leu(1)–Cys(2)–OMe 4, Boc–Leu(1)–Cys(2)–OMe 5 and Boc–Val(1)–Cys(2)–OMe 6 are formed and all of them failed to form any kind of fibril under the same conditions, indicating the important role of the disulfide bond in amyloid-like fibrillogenesis in a peptide model system.

Graphical abstract: The role of the disulfide bond in amyloid-like fibrillogenesis in a model peptide system

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Article information

DOI
https://doi.org/10.1039/B509083K
Article type
Paper
Submitted
28 Jun 2005
Accepted
20 Jul 2005
First published
11 Aug 2005

Org. Biomol. Chem., 2005,3, 3502-3507

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The role of the disulfide bond in amyloid-like fibrillogenesis in a model peptide system

A. Kumar Das, M. G. B. Drew, D. Haldar and A. Banerjee, Org. Biomol. Chem., 2005, 3, 3502 DOI: 10.1039/B509083K

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