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Borohydride Reduction of EstroneAnimesh Aditya, David E. Nichols, and G. Marc Loudon This experiment presents a guided-inquiry approach to the demonstration of diastereoselectivity using chiral hindered ketones that undergo facile reduction with sodium borohydride. The resulting diastereomeric estradiols can be analyzed and differentiated by thin-layer chromatography and melting point. Aditya, Animesh; Nichols, David E.; Loudon, G. Marc. J. Chem. Educ.2008, 85, 1535.
Aldehydes / Ketones |
Diastereomers |
IR Spectroscopy |
Microscale Lab |
Stereochemistry |
Steroids |
Thin Layer Chromatography
Isolation of Betulin and Rearrangement to AllobetulinBrian Green, Michael D. Bentley, Bong Y. Chung, Nicholas G. Lynch, and Bruce L. Jensen Betulin is obtained by extraction from birch bark and converted to allobetulin. Both compounds display 1H NMR spectra that include axialequatorial coupling characteristic of a C3-alcohol, conformational analysis by the use of dihedral angles and the Karplus equation, coupling patterns caused by diastereotopic protons and long-range interactions, and chemical shift values that are influenced by electronegativity and stereochemistry. Green, Brian; Bentley, Michael D.; Chung, Bong Y.; Lynch, Nicholas G.; Jensen, Bruce L. J. Chem. Educ.2007, 84, 1985.
Biosynthesis |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Natural Products
Nature's Way To Make the LantibioticsHeather A. Relyea and Wilfred A. van der Donk This article focuses on one class of antimicrobial compounds, the lantibiotics, and discusses their biosynthetic pathways as well as their molecular mode of action. In the course of the review, the meaning of the terms regio-, chemo-, and stereoselectivity are discussed. Relyea, Heather A.; van der Donk, Wilfred A. J. Chem. Educ.2006, 83, 1769.
The Building Blocks of BiochemistryEd Vitz, John W. Moore A section of ChemPrime, the Chemical Educations Digital Library's free General Chemistry textbook.
Biosynthesis
Transcription and TranslationEd Vitz, John W. Moore A section of ChemPrime, the Chemical Educations Digital Library's free General Chemistry textbook.
