Stabilization of an alpha helix by beta-sheet-mediated self-assembly of a macrocyclic peptide.

Abstract

Protein roll call: Peptide-based building blocks, in which both an alpha-helix-forming segment and a beta-sheet segment are located within a single macrocyclic structure, self-assemble into alpha-helix-decorated artificial proteins. This approach provides a starting point for developing artificial proteins that can modulate alpha-helix-mediated interactions occurring in a multivalent fashion.

Full text

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Supporting Information
© Wiley-VCH 2009
69451 Weinheim, Germany

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Supporting Information

Stabilization of α α-Helix by β β-Sheet-mediated Self-Assembly of
Macrocyclic Peptide
Yong-beom Lim, Kyung-Soo Moon & Myongsoo Lee*
Center for Supramolecular Nano-Assembly and Department of Chemistry, Yonsei
University, Seoul 120-749, Korea

H
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NH2
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H2N
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NH
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HO
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NH2
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Peptide 4
Boc
tBu
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i
ii


Figure S1. Synthesis of macrocyclic peptide. (i) 1% DIPEA in NMP; (ii) 95% TFA, 2.5% 1,2-
ethanedithiol, 2.5% thioanisole.

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H2N
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NH2
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NH2
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OH
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OH
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NH2
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H2N
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NH2
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Peptide 1
Peptide 2
Peptide 4
Peptide 3
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NH2
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H2N
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HO
N
H
HO
O


Figure S2. Structures of peptide 1, 2, 3, and 4.

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Figure S3. MALDI-TOF MS spectra of a) peptide 1, b) peptide 2, c) peptide 3, and d) peptide 4.
Matrix: α-cyano-4-hydroxycinnamic acid.

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Figure S4. CD spectra of peptide 2 at various temperatures.