Chapter 10 - Nitrogen and Phosphorus containing compounds

all amino acids have a chiral center except

glycine

orientation of amino acids

all are S except cysteine

peptide bonds

form by condensation reactions and can be cleaved hydrolytically

resonance of the peptide bond restricts

motion about the C-N bond which takes on partial double bond character

what is needed to cleave a peptide

strong acid or base

strecker synthesis

generates an amino acid from an aldehyde

process of strecker synthesis

an aldehyde is mixed with ammonium chloride and potassium cyanide, the ammonia attacks the carbonyl generating an imine, the imine is attacked by the cyanide generating an aminonitrile, the aminonitrile is hydrolyzed by 2 equivalents of water

gabriel synthesis

generates an amino acid from potassium phthalimide diethyl bromomalonate and an alkyl halide

process of gabriel synthesis

phthalimide attacks the bromomalonate generating an ester, the ester attacks an alkyl halide adding an alkyl group to the ester, the product is hydrolyzed creating phthalic acid and converting the ester into carb acids, one carb acid of the resulting 1,3-dicarbonyl is removed by decarboxylation