Molbank (Mar 2020)

Unexpected Seven-Membered Ring Formation for Muraymycin-Type Nucleoside-Peptide Antibiotics

  • Kristin Leyerer,
  • Stefan Koppermann,
  • Christian Ducho

DOI
https://doi.org/10.3390/M1122
Journal volume & issue
Vol. 2020, no. 2
p. M1122

Abstract

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Naturally occurring nucleoside-peptide antibiotics such as muraymycins or caprazamycins are of major interest for the development of novel antibacterial agents. However, the synthesis of new analogues of these natural products for structure−activity relationship (SAR) studies is challenging. In our synthetic efforts towards a muraymycin-derived nucleoside building block suitable for attachment to a solid support, we came across an interesting side product. This compound resulted from an undesired Fmoc deprotection with subsequent cyclization, thus furnishing a remarkable caprazamycin-like seven-membered diazepanone ring.

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