Issue 14, 2013

Photochemical thiol–yne functionalization of polypeptide scaffolds

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

Supplementary files

Article information

Article type
Paper
Submitted
02 Apr 2013
Accepted
01 May 2013
First published
01 May 2013

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

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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