Crystallomycin revisited after 60 years: aspartocins B and C

MedChemComm
2018.0

Abstract

The study of an archived sample of crystallomycin complex using HPLC, ESI HRMS, and 2D NMR showed that two major components of the antibiotic, compounds <b>1</b> and <b>2</b>, are lipopeptides having the same peptide core, Asp1-cyclo(Dab2-Pip3-MeAsp4-Asp5-Gly6-Asp7-Gly8-Dab9-Val10-Pro11-), <i>N</i>-acylated either with Δ<sup>3</sup>-iso-tetradecenoyl or Δ<sup>3</sup>-anteiso-pentadecenoyl that are identical to aspartocins C and B, respectively. According to the 2D NMR study, compound <b>2</b> in DMSO solution exists as a mixture of four conformers. The producing strain was identified as <i>Streptomyces griseorubens</i>. Compounds <b>1</b> and <b>2</b> have considerable Ca<sup>2+</sup>-dependent activity against Gram-positive bacteria including five MRSA strains.

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