Impact of Dehydroamino Acids on the Structure and Stability of Incipient 310-Helical Peptides

• Published in: Journal of organic chemistry Vol. 85; no. 3; pp. 1601 - 1613
• Main Authors: Joaquin, Daniel, Lee, Michael A, Kastner, David W, Singh, Jatinder, Morrill, Shardon T, Damstedt, Gracie, Castle, Steven L
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 07.02.2020; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; DESIGN; CONFORMATIONAL PROPERTIES; CRYSTAL-STRUCTURE; AMINO-ACIDS; NMR STRUCTURE CALCULATION; GAMMA-AAPEPTIDES; ALPHA,BETA-DEHYDRO RESIDUES; ENZYME STABILITY; LINEAR PEPTIDES; STEREOSPECIFIC DEHYDRATION

A comparative study of the impact of small, medium-sized, and bulky α,β-dehydroamino acids (ΔAAs) on the structure and stability of Balaram’s incipient 310-helical peptide (1) is reported. Replacement of the N-terminal Aib residue of 1 with a ΔAA afforded peptides 2a–c that maintained the 310-helica...