Issue 14, 2013
From the journal:

Polymer Chemistry

Photochemical thiol–yne functionalization of polypeptide scaffolds†

Kai-Steffen Krannig,a   Jin Huang,b   Andreas Heiseb  and  Helmut Schlaad*a  

* Corresponding authors

a Max Planck Institute of Colloids and Interfaces, Department of Colloid Chemistry, Research Campus Golm, Germany
E-mail: Helmut.Schlaad@mpikg.mpg.de

b Dublin City University, School of Chemical Sciences, Glasnevin, Dublin 9, Ireland

Abstract

Copolypeptides with propargyl side chains were functionalized with different thiols (1-thio-β-D-glucose tetraacetate, 7-mercapto-4-methylcoumarin, and methyl-3-mercaptopropionate) by initiator/catalyst-free thiol–yne photochemistry. No more than 1.5 instead of ideally 2 equivalents of thiol could be added to the propargyl units even when the thiol was used in excess, attributable to steric constraints (close proximity of the reaction site to the copolypeptide backbone) or conjugation (extended aromatic system). Nevertheless, this procedure enables a facile and modular synthesis of highly functionalized homo- and hetero-functional copolypeptides.

Graphical abstract: Photochemical thiol–yne functionalization of polypeptide scaffolds

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Article information

DOI
https://doi.org/10.1039/C3PY00428G
Article type
Paper
Submitted
02 Apr 2013
Accepted
01 May 2013
First published
01 May 2013

Polym. Chem., 2013,4, 3981-3986

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Photochemical thiol–yne functionalization of polypeptide scaffolds

K. Krannig, J. Huang, A. Heise and H. Schlaad, Polym. Chem., 2013, 4, 3981 DOI: 10.1039/C3PY00428G

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