Amino acid synthesis

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  • Created by: SamDavies
  • Created on: 22-04-19 18:55
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  • Amino acid synthesis
    • Strecker synthesis
      • Reagents: aldehyde amine and HCN
      • End product is racemic mixture
      • Intermediate is alpha amino nitrile
      • Reagents for hydrolysis of amino nitrile: H3O+, H2O and heat
    • Using carboxylic acid derivatives
      • Acyl chloride + amine ==> amide + HCl
        • Cl is a good leaving group
      • Carboxylic anhydride + secondary amine ==> amide + carboxylic acid
      • Ester + secondary amine ==> amide + alcohol
        • Reagents: acid or base + heat
    • Using carbodiimide agents, e.g. DCC
      • Reagents: DCC, carboxylic acid, secondary amine
      • Produces amide and stable urea product
    • Amino acid hydrolysis
      • Acidic hydrolysis
        • Amino acid + H3O+ ==> Carboxylic acid + NH4+
        • Also uses H2O and heat
          • Basic hydrolysis
            • Amino acid + OH- ==> carboxylate ion + NH3
      • Basic hydrolysis
        • Amino acid + OH- ==> carboxylate ion + NH3

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