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Issue 7, 2011
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Multi-functionalization of helical block copoly(α-peptide)s by orthogonal chemistry

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Abstract

Diblock copoly(α-peptide)s bearing functional side-chains (i.e., azido or allyl) that are readily derivatized by “click” chemistry have been synthesized by primary amine-initiated sequential polymerization of the corresponding N-carboxyanhydrides (NCAs). Facile derivation of the side-chains has been demonstrated, in which mannose moieties are quantitatively attached via the alkyneazide [2 + 3] Huisgen cycloaddition to form amphiphilic block copoly(α-peptide)s that retain their helical conformations in solution. Allyl side-chains residing in the hydrophobic core can be further functionalized with high efficiency by radical thiol–ene addition reactions despite the tendency of the amphiphilic precursors to aggregate.

Graphical abstract: Multi-functionalization of helical block copoly(α-peptide)s by orthogonal chemistry

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Publication details

The article was received on 13 Jan 2011, accepted on 16 Feb 2011 and first published on 11 Mar 2011


Article type: Paper
DOI: 10.1039/C1PY00015B
Polym. Chem., 2011,2, 1542-1551

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    Multi-functionalization of helical block copoly(α-peptide)s by orthogonal chemistry

    H. Tang and D. Zhang, Polym. Chem., 2011, 2, 1542
    DOI: 10.1039/C1PY00015B

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