Efficient synthesis of protein mimics by sequential native chemical ligation

Helmus van de Langemheen; H Linda C Quarles van Ufford; John A W Kruijtzer; Rob M J Liskamp

doi:10.1021/ol500604h

Efficient synthesis of protein mimics by sequential native chemical ligation

Helmus van de Langemheen, H Linda C Quarles van Ufford, John A W Kruijtzer, Rob M J Liskamp

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

Synthetic mimics of protein surfaces have the potential to become inhibitors of protein-protein interactions or even synthetic vaccines. However, the synthesis of these complicated molecular constructs is still difficult. Here we describe an efficient and versatile synthesis of protein mimics containing up to three different cyclic peptides. Using a sequential native chemical ligation strategy, peptide loops containing a thioester handle were introduced onto a triazacyclophane scaffold bearing orthogonal protected cysteine residues.

Original language	English
Pages (from-to)	2138-41
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	8
DOIs	https://doi.org/10.1021/ol500604h
Publication status	Published - 18 Apr 2014

Keywords

Aza Compounds
Cysteine
Heterocyclic Compounds, 2-Ring
Molecular Structure
Peptides, Cyclic

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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Cite this

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AU - van de Langemheen, Helmus

AU - Quarles van Ufford, H Linda C

AU - Kruijtzer, John A W

AU - Liskamp, Rob M J

PY - 2014/4/18

Y1 - 2014/4/18

N2 - Synthetic mimics of protein surfaces have the potential to become inhibitors of protein-protein interactions or even synthetic vaccines. However, the synthesis of these complicated molecular constructs is still difficult. Here we describe an efficient and versatile synthesis of protein mimics containing up to three different cyclic peptides. Using a sequential native chemical ligation strategy, peptide loops containing a thioester handle were introduced onto a triazacyclophane scaffold bearing orthogonal protected cysteine residues.

AB - Synthetic mimics of protein surfaces have the potential to become inhibitors of protein-protein interactions or even synthetic vaccines. However, the synthesis of these complicated molecular constructs is still difficult. Here we describe an efficient and versatile synthesis of protein mimics containing up to three different cyclic peptides. Using a sequential native chemical ligation strategy, peptide loops containing a thioester handle were introduced onto a triazacyclophane scaffold bearing orthogonal protected cysteine residues.

KW - Aza Compounds

KW - Cysteine

KW - Heterocyclic Compounds, 2-Ring

KW - Molecular Structure

KW - Peptides, Cyclic

U2 - 10.1021/ol500604h

DO - 10.1021/ol500604h

M3 - Article

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JO - Organic Letters

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ER -

Efficient synthesis of protein mimics by sequential native chemical ligation

Abstract

Keywords

UN SDGs

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