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Issue 8, 2012
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Peptide and glycopeptide dendrimer apple trees as enzyme models and for biomedical applications

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Abstract

Solid phase peptide synthesis (SPPS) provides peptides with a dendritic topology when diamino acids are introduced in the sequences. Peptide dendrimers with one to three amino acids between branches can be prepared with up to 38 amino acids (MW ∼ 5,000 Da). Larger peptide dendrimers (MW ∼ 30,000) were obtained by a multivalent chloroacetyl cysteine (ClAc) ligation. Structural studies of peptide dendrimers by CD, FT-IR, NMR and molecular dynamics reveal molten globule states containing up to 50% of α-helix. Esterase and aldolase peptide dendrimers displaying dendritic effects and enzyme kinetics (kcat/kuncat ∼ 105) were designed or discovered by screening large combinatorial libraries. Strong ligands for Pseudomonas aeruginosa lectins LecA and LecB able to inhibit biofilm formation were obtained with glycopeptide dendrimers. Efficient ligands for cobalamin, cytotoxic colchicine conjugates and antimicrobial peptide dendrimers were also developed showing the versatility of dendritic peptides. Complementing the multivalency, the amino acid composition of the dendrimers strongly influenced the catalytic or biological activity obtained demonstrating the importance of the “apple tree” configuration for protein-like function in peptide dendrimers.

Graphical abstract: Peptide and glycopeptide dendrimer apple trees as enzyme models and for biomedical applications

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Publication details

The article was received on 18 Nov 2011, accepted on 19 Dec 2011 and first published on 20 Dec 2011


Article type: Perspective
DOI: 10.1039/C2OB06938E
Citation: Org. Biomol. Chem., 2012,10, 1483-1492
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    Peptide and glycopeptide dendrimer apple trees as enzyme models and for biomedical applications

    J. Reymond and T. Darbre, Org. Biomol. Chem., 2012, 10, 1483
    DOI: 10.1039/C2OB06938E

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