The Design and Synthesis of Alanine-Rich α-Helical Peptides Constrained by an S,S-Tetrazine Photochemical Trigger: A Fragment Union Approach

详细信息    查看全文

• 作者：Joel R. Courter ; Mohannad Abdo ; Stephen P. Brown ; Matthew J. Tucker ; Robin M. Hochstrasser ; Amos B. Smith ; III
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：January 17, 2014
• 年：2014
• 卷：79
• 期：2
• 页码：759-768
• 全文大小：541K
• ISSN：1520-6904

文摘

The design and synthesis of alanine-rich 伪-helical peptides constrained in a partially unfolded state by incorporation of the S,S-tetrazine phototrigger has been achieved, permitting, upon photochemical release, observation by 2D-IR spectroscopy of the subnanosecond conformational dynamics that govern the early steps associated with 伪-helix formation. Solid-phase peptide synthesis was employed to elaborate the requisite fragments, with full peptide construction via solution-phase fragment condensation. The fragment union tactic was also employed to construct ¹³C鈺?sup>18O isotopically edited amides to permit direct observation of conformational motion at or near specific peptide bonds.