Lecture34outline - • Conducting the Strecker synthesis...

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I. Review • The central dogma of molecular biology states that DNA directs the formation of messenger RNA (mRNA) that provides a template for transfer RNA (tRNA) organization en route to protein synthesis • Proteins are polymers of α -amino acids that are linked together by amide bonds • The substituent (side chain) at the α -position of the amino acid can have several properties, including hydrophobicity, acidity, basicity, aromaticity, and nucleophilicity • The sequence of amino acids and the properties of the side chains control the overall structure of the protein and confer its function • Chemical synthesis of amino acids is necessary when preparing peptides or proteins that have subunits that aren't available in nature • The Strecker synthesis forms racemic amino acids, but natural amino acids are formed as single enantiomers
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Unformatted text preview: • Conducting the Strecker synthesis with a chiral Lewis acid rather than HOAc leads to the formation of enantiomerically enriched amino nitriles that can be converted to single enantiomers of amino acids • Chiral derivatives of glycine can be converted to enolates for diastereoselective addition to electrophiles to form amino acid derivatives through carbon–carbon bond formation • Chiral enolates can react with notrogen electrophiles like DEAD to form amino acid derivatives through carbon–nitrogen bond formation • Amino acids cannot be coupled efficiently in the absence of protecting groups II. More amino acid chemistry • Peptide synthesis • Automated synthesis • Coupling large peptide fragments Problem Set 26-4, 26-5, 26-7, 26-8, 26-14, 26-16, 26-17, 26-18, 26-19, 26-20, 26-22, 26-31, 26-32, 26-38, 26-48, 26-52...
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This note was uploaded on 05/17/2010 for the course CHEM 0740 taught by Professor Professor during the Spring '10 term at Pittsburgh.

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Lecture34outline - • Conducting the Strecker synthesis...

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