Synthesis, Structure–Activity Analysis, and Biological Evaluation of Sanguinamide B Analogues

H Wahyudi, W Tantisantisom, X Liu…

Index: Wahyudi, Hendra; Tantisantisom, Worawan; Liu, Xuechao; Ramsey, Deborah M.; Singh, Erinprit K.; McAlpine, Shelli R. Journal of Organic Chemistry, 2012 , vol. 77, # 23 p. 10596 - 10616

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Citation Number: 18

Abstract

We report the first synthesis of sanguinamide B analogues. Substituting N-methylated (N- Me) amino acids, glycine (Gly), and l-or d-phenylalanine (Phe) into the backbone of sanguinamide B showed that only l-and d-Phe residues controlled the macrocycle conformation. The N-methylated and glycine analogues all had multiple conformations, whereas the l-and d-Phe derivatives only had a single conformation. Testing of all ...