Assignment of the Liposidomycin Diazepanone Stereochemistry

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 reg...

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Bibliographic Details
Published in:Journal of organic chemistry 2001-08, Vol.66 (17), p.5822-5831
Main Authors: Knapp, Spencer, Morriello, Gregori J, Nandan, Santosh R, Emge, Thomas J, Doss, George A, Mosley, Ralph T, Chen, Lijian
Format: Article
Language:English
Subjects:
Amination
Aminoglycosides
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Models, Molecular
Molecular Conformation
Oxidation-Reduction
Stereoisomerism
Valine - analogs & derivatives
Valine - chemistry
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Summary: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)].
ISSN:0022-3263
1520-6904
DOI:10.1021/jo010355g