Department of Chemistry, Toho University, Funabashi, Chiba 274-8510, Japan.
Org Biomol Chem. 2010 Apr 21;8(8):1791-7. doi: 10.1039/b922159j.
Antimicrobially active cycloundecapeptides related to gramicidin S, cyclo(-Val1-Orn2-Leu3-X4-D-Phe5-Pro6-Val7-Orn8- Leu9-D-Phe10-Pro11-) (X= Leu (1), Ala (2), Orn (3), Lys (4) and Arg (5)), were synthesized. From the CD and NMR studies, 1-5 possess antiparallel -sheet conformation linked by a type II -turn around D-Phe10-Pro11 and a novel turn structure around X4-D-Phe5-Pro6 sequence with cis D-Phe-Pro peptide bond. The structural modifications at position 4 of 1-5 are beneficial to identification of novel antibiotic candidates without hemolytic activity.
抗菌环十一肽与短杆菌肽 S 相关，环(-缬氨酰基-鸟氨酰基-亮氨酰基-X4-D-苯丙氨酰基-脯氨酰基-缬氨酰基-鸟氨酰基-亮氨酰基-D-苯丙氨酰基-脯氨酰基-)-（X=亮氨酸（1）、丙氨酸（2）、鸟氨酸（3）、赖氨酸（4）和精氨酸（5））被合成。通过 CD 和 NMR 研究，1-5 具有通过 D-Phe10-Pro11 处的 II 型 -转角连接的反平行 -折叠构象，以及在 X4-D-Phe5-Pro6 序列周围的新型转角结构，脯氨酰基-顺式 D-苯丙氨酸肽键。1-5 中 4 位的结构修饰有利于鉴定无溶血活性的新型抗生素候选物。
