Design of a stabilized short helical peptide and its application to catalytic enantioselective epoxidation of (E)-chalcone

作者：Yamagata Nanako; Demizu Yosuke^*; Sato Yukiko; Doi Mitsunobu; Tanaka Masakazu; Nagasawa Kazuo; Okuda Haruhiro; Kurihara Masaaki

来源：Tetrahedron Letters, 2011, 52(7): 798-801.

DOI：10.1016/j.tetlet.2010.12.030

• Peptide
• Helix
• X-ray crystallographic analysis
• Organocatalyst
• Enantioselective epoxidation

Stabilized short helical heptapeptides containing a combination of an alpha-aminoisobutyric acid as a helical promoter and L/D-serine derivatives to produce cross-linked units were synthesized. The cyclic peptide R3,7R-(2), which had D-serine derivatives at its 3rd and 7th positions, formed a stable right-handed (P) alpha-helix in solution and the crystalline state. Furthermore, its N-terminal free helical peptide catalyzed the enantioselective epoxidation of (E)-chalcone to afford the epoxide in a high yield and moderate enantioselectivity.

• 出版日期2011-2-16