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Showing 1 to 2 of 2 for “"conformationally locked isostere"”.
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I. Collagen-like polypeptides. II. Helix-turn-helix peptides and turn mimetics
… steps during collagen triple helix folding. The conformationally locked alkene isosteres Fmoc-Gly-Ψ[(E)CH=C]-Pro-Hyp(tBu)-OH and Fmoc-Pro-Ψ[(E)CH=C]-Pro-OH were designed and synthesized. The synthesis of the Gly-Pro isostere had no stereo-control, and the two diastereomers of the tripeptide …
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Isomerization-Locked Alkene Analogues of Xaa–Pro Dipeptides in the Proteins Collagen and Bora
… However, eliminating isomerization with a trans-locked alkene isostere destabilizes collagen-like peptides. Collagen is stabilized by electronic interactions, namely the n→π* interaction. Halo-alkene isosteres may be used to recapture these electronic interactions and stabilize a collagen-like …