Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 23, Pages 9228-9234Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo8012429
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Funding
- Victoria S. and Bradley L. Geist Foundation [20070461]
- National Science Foundation [OCE04-32479, CH E9974921]
- National Institute of Environmental Health Sciences [P50 ES012740]
- Elsa Pardee Foundation
- Department of Defense [W911NF-04-1-0344]
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A simple method to determine the relative stereochemistry of statine amino acids (gamma-amino-beta-hydroxyacids) by using H-1 NMR spectroscopy is described. Configurational assignment of statine units within complex natural products is possible without degradation or derivatization as the syn and anti diastereomers can be distinguished by using a combination of chemical shift and coupling constant information derived from the a-methylene ABX system. Seventy-three examples are provided, demonstrating the scope and limitations of the methodology. These examples range in complexity from simple statine units to cyclic depsipeptides, such as tamandarin B.
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