4.8 Article

Switchable Proline Derivatives: Tuning the Conformational Stability of the Collagen Triple Helix by pH Changes

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 39, Pages 10340-10344

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201404935

Keywords

collagen; PPII helix; proline; ring pucker; stereoelectronic effects

Funding

  1. NCCR NANO
  2. Bachem
  3. SSCI fellowship

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(4S)-Aminoproline is introduced as a pH-sensitive probe for tuning the conformational properties of peptides and proteins. The pH-triggered flip of the ring puckering and the formation/release of a transannular H bond were used to switch the formation of collagen triple helices on and off reversibly.

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