Synthesis of chiral monoaza-15-crown-5 ethers from a chiral amino alcohol and enantiomeric recognition of potassium and sodium salts of amino acids

The enantiomeric recognition of chiral monoaza-crown ethers for amino acids as their sodium and potassium salts has been investigated by UV–vis. The highest discrimination was observed for TrpK (d/l = 6.47). The reversed enantioselectivity of chiral monoaza-crown ether II was observed for TrpK.

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(R)-(−)-N-Benzyl-2-amino-1-butanolC11H17NO[α]D20=-25.6 (c 0.08, EtOH)Source of chirality: (R)-(−)-2-amino-1-butanolAbsolute configuration: R

(R)-(−)-N-Benzyl-4-hydroxymethyl-3-azahexane-1-olC13H21NO2[α]D20=-14.9 (c 0.08, EtOH)Source of chirality: (R)-(−)-2-amino-1-butanolAbsolute configuration: R

(R)-(−)-2-Ethyl-N-benzyl-4,7,10,13-tetraoxa-8,9-benzo-1-azacyclopentadec-8-eneC19H31NO4[α]D20=-28.8 (c 0.04, EtOH)Source of chirality: (R)-(−)-2-amino-1-butanolAbsolute configuration: R

(R)-(−)-2-Ethyl-N-benzyl-4,7,10,13-tetraoxa-8,9-benzo-1-azacyclopentadec-8-eneC23H31NO4[α]D20=-2.2 (c 0.04, EtOH)Source of chirality: (R)-(−)-2-amino-1-butanolAbsolute configuration: R