Laboratorium für Organische Chemie, ETH Zürich, Wolfgang-Pauli-Strasse 10, 8093 Zürich, Switzerland.
Bioorg Med Chem. 2013 Jun 15;21(12):3565-8. doi: 10.1016/j.bmc.2013.02.046. Epub 2013 Mar 14.
Functionalized collagen is attractive for the development of synthetic biomaterials. Herein we present the functionalization of azidoproline containing collagen model peptides with various alkynes using click chemistry. The influence on the stability of the collagen triple helix of the stereochemistry of the introduced triazolyl prolines (4R or 4S), the position of their incorporation (Xaa or Yaa) and the substituents attached to them are shown. The results provide a useful guide for the optimal functionalization of collagen using click chemistry.
功能化胶原蛋白是合成生物材料的理想选择。本研究通过点击化学，将含有叠氮基脯氨酸的胶原蛋白模型肽与各种炔烃进行了功能化。结果表明，引入的三唑基脯氨酸的立体化学（4R 或 4S）、取代位置（Xaa 或 Yaa）以及取代基对胶原蛋白三螺旋稳定性的影响。该结果为利用点击化学对胶原蛋白进行最佳功能化提供了有用的指导。
