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Issue 48, 2018

Homoallylglycine residues are superior precursors to orthogonally modified thioether containing polypeptides

Author affiliations

Abstract

Homoallylglycine N-carboxyanhydride, Hag NCA, monomers were synthesized and used to prepare polypeptides containing Hag segments with controllable lengths of up to 245 repeats. Poly(L-homoallylglycine), GHA, was found to adopt an α-helical conformation, which provided good solubility in organic solvents and allowed high yield functionalization of its alkene side-chains via radical promoted addition of thiols. The conformations of these derivatives were shown to be switchable between α-helical and disordered states in aqueous media using thioether alkylation or oxidation reactions. Incorporation of GHA segments into block copolymers with poly(L-methionine), M, segments provided a means to orthogonally modify thioether side-chains different ways in separate copolypeptide domains. This approach allows preparation of functional polypeptides containing discrete domains of oxidized and alkylated thioether containing residues, where chain conformation and functionality of each domain can be independently modified.

Graphical abstract: Homoallylglycine residues are superior precursors to orthogonally modified thioether containing polypeptides

Supplementary files

Article information


Submitted
16 Apr 2018
Accepted
25 May 2018
First published
25 May 2018

Chem. Commun., 2018,54, 6196-6199
Article type
Communication
Author version available

Homoallylglycine residues are superior precursors to orthogonally modified thioether containing polypeptides

P. Perlin, E. G. Gharakhanian and T. J. Deming, Chem. Commun., 2018, 54, 6196 DOI: 10.1039/C8CC03048K

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