Assignment of the liposidomycin diazepanone stereochemistry

S. Knapp, G. J. Morriello, S. R. Nandan, T. J. Emge, G. A. Doss, R. T. Mosley, L. Chen

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38 Scopus citations

Abstract

The liposidomycins comprise a family of complex nucleoside antibiotics that inhibit bacterial peptidoglycan synthesis. Their structures (1, 2) feature nucleoside, ribofuranoside, diazepanone, and lipid regions. Several stereogenic centers remain unassigned, including three within the diazepanone region: C-6′, C-2‴, and C-3‴. An intramolecular reductive amination reaction has been used to prepare model diazepanones. Analysis of 40 and two of its diastereomers by NMR spectroscopy, X-ray crystallography, and molecular modeling indicates a close relative configurational and conformational match between 40 and the liposidomycin diazepanone degradation product 43 and allows the assignment of stereochemistry of the natural products as either [C-6′(R), C-2‴(R), C-3‴(R)] or [C-6′(S), C-2‴(S), C-3‴(S)].

Original languageEnglish (US)
Pages (from-to)5822-5831
Number of pages10
JournalJournal of Organic Chemistry
Volume66
Issue number17
DOIs
StatePublished - Aug 24 2001

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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