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Journal Article
Research Support, Non-U.S. Gov't
Crystal-to-Crystal Synthesis of Triazole-Linked Pseudo-proteins via Topochemical Azide-Alkyne Cycloaddition Reaction.
Journal of the American Chemical Society 2016 November 17
Isosteric replacement of amide bond(s) of peptides with surrogate groups is an important strategy for the synthesis of peptidomimetics (pseudo-peptides). Triazole is a well-recognized bio-isostere for peptide bonds, and peptides with one or more triazole units are of great interest for different applications. We have used a catalyst-free and solvent-free method, viz., topochemical azide-alkyne cycloaddition (TAAC) reaction, to synthesize pseudo-proteins with repeating sequences. A designed β-sheet-forming l-Ala-l-Val dipeptide containing azide and alkyne at its termini (N3 -Ala-Val-NHCH2 C≡CH, 1) was synthesized. Single-crystal XRD analysis of the dipeptide 1 showed parallel β-sheet arrangement along the b-direction and head-to-tail arrangement of such β-sheets along the c-direction. This head-to-tail arrangement along the c-direction places the complementary reacting motifs, viz., azide and alkyne, of adjacent molecules in proximity. The crystals of dipeptide 1, upon heating at 85 °C, underwent crystal-to-crystal polymerization, giving 1,4-triazole-linked pseudo-proteins. This TAAC polymerization was investigated by various time-dependent techniques, such as NMR, IR, DSC, and PXRD. The crystal-to-crystal nature of this transformation was revealed from polarizing microscopy and PXRD experiments, and the regiospecificity of triazole formation was evidenced from various NMR techniques. The MALDI-TOF spectrum showed the presence of pseudo-proteins >7 kDa.
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