Zelkovamycins B–E, Cyclic Octapeptides Containing Rare Amino Acid Residues from an Endophytic <i>Kitasatospora</i> sp
Xiaomeng Hao, Jiaqing Yu, Yujia Wang, Jack A. Connolly, Yufeng Liu, Yu‐Qin Zhang, Liyan Yu, Shan Cen, Rebecca J. M. Goss, Maoluo Gan
Abstract
Four unusual cyclopeptides, zelkovamycins B–E (1–4), were isolated from an endophytic Kitasatospora sp. Zelkovamycin B was featured by an unprecedented 3-methyl-5-hydroxypyrrolidine-2,4-dione ring system linked to the cyclopeptide skeleton. Their structures and full configurations were established by spectroscopic analysis, Marfey’s method, and NMR calculations. A plausible biosynthetic pathway for zelkovamycins was proposed based on gene cluster analysis. Zelkovamycin E displayed potent inhibitory activity against H1N1 influenza A virus.
Topics & Concepts
ChemistryStereochemistryCyclic peptideAmino acidSide chainRing (chemistry)Two-dimensional nuclear magnetic resonance spectroscopyGene clusterInhibitory postsynaptic potentialPeptideGeneBiochemistryBiologyOrganic chemistryPolymerNeuroscienceMicrobial Natural Products and BiosynthesisChemical Synthesis and AnalysisSynthetic Organic Chemistry Methods