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Confirmation of the absolute configuration of Stachybotrin C using single-crystal X-ray diffraction analysis of its 4-bromobenzyl ether derivative
- Source :
- The Journal of Antibiotics. 71:584-591
- Publication Year :
- 2018
- Publisher :
- Springer Science and Business Media LLC, 2018.
-
Abstract
- The absolute configuration of Stachybotrin C was confirmed in this study. After synthesizing the dimethyl ethers of Stachybotrin C, the C-8 epimer was analyzed by 1D NOESY. However, the stereochemistry determination was difficult through the NOE correlations. Instead, the di(4-bromobenzyl) ether of Stachybotrin C was derived and used for X-ray diffraction analysis, because its single crystal was easier to obtain than that of the original Stachybotrin C. The stereochemistry of Stachybotrin C was determined to be (8S, 9R). This derivatization approach may also be used to prepare single crystals of the analogues.
- Subjects :
- Models, Molecular
Indoles
Magnetic Resonance Spectroscopy
Materials science
Molecular Conformation
Ether
010402 general chemistry
01 natural sciences
chemistry.chemical_compound
X-Ray Diffraction
Drug Discovery
Benzopyrans
Nerve Growth Factors
Derivatization
Pharmacology
Molecular Structure
010405 organic chemistry
Absolute configuration
Stereoisomerism
Nuclear magnetic resonance spectroscopy
0104 chemical sciences
Crystallography
chemistry
X-ray crystallography
Epimer
Crystallization
Single crystal
Derivative (chemistry)
Subjects
Details
- ISSN :
- 18811469 and 00218820
- Volume :
- 71
- Database :
- OpenAIRE
- Journal :
- The Journal of Antibiotics
- Accession number :
- edsair.doi.dedup.....8aa0ee0ac2da730aa08c9f2dbbf49eb5