Lecture34outline

Lecture34outline - Conducting the Strecker synthesis with a...

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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 carboncarbon bond formation Chiral enolates can react with notrogen electrophiles like DEAD to form amino acid derivatives through carbonnitrogen 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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Lecture34outline - Conducting the Strecker synthesis with a...

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