β-Sheet to Helical-Sheet Evolution Induced by Topochemical Polymerization: Cross-α-Amyloid-like Packing in a Pseudoprotein with Gly-Phe-Gly Repeats.

Angewandte Chemie
Kuntrapakam Hema, Kana M Sureshan

Abstract

Protein-mimics are of great interest for their structure, stability, and properties. We are interested in the synthesis of protein-mimics containing triazole linkages as peptide-bond surrogate by topochemical azide-alkyne cycloaddition (TAAC) polymerization of azide- and alkyne-modified peptides. The rationally designed dipeptide N3 -CH2 CO-Phe-NHCH2 CCH (1) crystallized in a parallel β-sheet arrangement and are head-to-tail aligned in a direction perpendicular to the β-sheet-direction. Upon heating, crystals of 1 underwent single-crystal-to-single-crystal polymerization forming a triazole-linked pseudoprotein with Gly-Phe-Gly repeats. During TAAC polymerization, the pseudoprotein evolved as helical chains. These helical chains are laterally assembled by backbone hydrogen bonding in a direction perpendicular to the helical axis to form helical sheets. This interesting helical-sheet orientation in the crystal resembles the cross-α-amyloids, where α-helices are arranged laterally as sheets.

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Citations

Jan 13, 2021·Proceedings of the National Academy of Sciences of the United States of America·Nir SalinasMeytal Landau
Feb 6, 2021·Chemical Society Reviews·Kuntrapakam HemaKana M Sureshan
Apr 23, 2021·The Journal of Physical Chemistry. B·Souvik MisraJayanta Nanda
Jun 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Naima AgouramAbdeslem Bentama
Aug 17, 2021·Angewandte Chemie·Mithun C MadhusudhananKana M Sureshan
Aug 12, 2021·Angewandte Chemie·Ravichandran Khazeber, Kana M Sureshan

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