Semisynthetic chemical modification of the antifungal lipopeptide echinocandin B (ECB): structure-activity studies of the lipophilic and geometric parameters of …

…, WW Turner, L LaGrandeur, FJ Burkhardt…

Index: Debono, Manuel; Turner, William W.; LaGrandeur, Lisa; Burkhadt, Fred J.; Nissen , Jeffrey S.; et al. Journal of Medicinal Chemistry, 1995 , vol. 38, # 17 p. 3271 - 3281

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Citation Number: 117

Abstract

Echinocandin B (ECB) is a lipopeptide composed of a complex cyclic peptide acylated at the N-terminus by linoleic acid. Enzymatic deacylation of ECB provided the peptide “nucleus” as a biologically inactive substrate from which novel ECB analogs were generated by chemical reacylation at the N-terminus. Varying the acyl group revealed that the structure and physical properties of the side chain, particularly its geometry and lipophilicity, played a pivotal role ...