Optical Resolution of 1,2-Diamino Compounds Using Advanced Marfey's Method

概要

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Advanced Marfeys method was successfully applied to the optical resolution of 1,2-diaminoethane compounds. The elution behavior of 1,2-diphenylethylene-1,2-diamine and 1,2-bis(2-methylphenyl)ethylene-1,2-diamine derivatized with L- and D-FDLA was carefully investigated and the following regularity was found: 1) The (S,S)-isomers are eluted prior to the (R,R)-isomer; 2) The (R,R)- and meso-isomers are closely eluted; 3) There is no difference between the retention time of both the L- and D-derivatives of the meso-isomer; 4) This regularity is fundamentally consistent with that of diamino acids such as diaminopimelic acid and diaminosuccinic acid. Finally, it was confirmed that this method along with the DL-FDLA method could be applicable for the determination of the absolute configuration of 1,2-diaminoethane compounds because the method can definitely determine it by the elution order.
2009-04-01