Topological Study of the Structures of Heterochiral Peptides Containing Equal Amounts of l-Leu and d-Leu

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• 作者：Yosuke Demizu ; Hiroko Yamashita ; Mitsunobu Doi ; Takashi Misawa ; Makoto Oba ; Masakazu Tanaka ; Masaaki Kurihara
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：September 4, 2015
• 年：2015
• 卷：80
• 期：17
• 页码：8597-8603
• 全文大小：501K
• ISSN：1520-6904

文摘

We designed and synthesized two dodecapeptides, Boc-(l-Leu-l-Leu-Aib-d-Leu-d-Leu-Aib)₂-OMe (5) and Boc-l-Leu-l-Leu-Aib-(d-Leu-d-Leu-Aib)₂-l-Leu-l-Leu-Aib-OMe (6), that contain equal amounts of l-Leu, d-Leu, and achiral Aib residues. The conformations of peptides 5 and 6 in the crystalline state were studied using X-ray crystallographic analysis. Peptide 5 formed a left-handed (M) 伪-helical structure, whereas peptide 6 was composed of a combination of fused (M) 伪-helical and right-handed (P) 3₁₀-helical structures. In solution, roughly equivalent amounts of (P) and (M) helices were present in 5, whereas the (M) 伪-helix was present in 6 as its dominant conformation.