Homoallylglycine residues are superior precursors to orthogonally modified thioether containing polypeptides

Chemical Communications : Chem Comm
Pesach PerlinTimothy J Deming

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.

References

Jun 30, 1998·FEBS Letters·J C van Hest, D A Tirrell
Nov 5, 2010·Biomacromolecules·Jessica R Kramer, Timothy J Deming
May 29, 2012·Biomacromolecules·Jessica R Kramer, Timothy J Deming
Oct 30, 2012·Journal of the American Chemical Society·Kai-Steffen Krannig, Helmut Schlaad
Aug 29, 2013·Biomacromolecules·April R RodriguezTimothy J Deming
Mar 25, 2014·Chemical Reviews·Kathrin Lang, Jason W Chin
Jul 7, 2015·Chemical Reviews·Timothy J Deming
May 11, 2016·ACS Central Science·Jessica R KramerTimothy J Deming
Jun 28, 2017·Biochemistry·Justine N deGruyterPhil S Baran

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Citations

Aug 26, 2020·Angewandte Chemie·Francisco José Aguilar TroyanoAdrián Gómez-Suárez
Mar 16, 2019·Biomacromolecules·Alexander L WollenbergTimothy J Deming

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Methods Mentioned

BETA
column chromatography
Circular dichroism

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