65(P33) 一級アミノ化合物の絶対配置決定のためのキラル異方性試薬の開発(ポスター発表の部)

概要

論文の詳細を見る
The advanced Marfey's method including DL-FDLA derivatization is non-empirical method for determination of the absolute configuration of primary aminno compounds including amino acids using LC/MS (Fig. 1(A)). In this method, their absolute configuration can then be determined based on their elution order under reversed phase conditions. We have proposed a separation mechanism for the resolution of both resulting diastereomers, which includes a stable and fixed conformation assisted by the intramolecular hydrogen bondings between the nitro groups and α-amino groups of the target compound and the leucinamide moiety. This conformation can be readily confirmed by UV spectral analysis and an NOE experiment. If this fixed conformation can also be formed in the case of (R, S)-FDPEA, it is expected to be available as a chiral anisotropic reagent for the determination of absolute configuration of primary amino compounds including amino acids (Fig. 1 (B)). We tried to confirm the absolute configuration of several primary amino compounds and C-3 of Ahda in microginin from cyanobacteria by (R, S)-FDPEA method (Figs. 3 and 4). Through these experiments, we established another non-empirical method for the determination of the absolute configuration of a primary amino compound using NMR spectroscopy (Fig. 2), which has the following advantages over conventional methods: (1) Derivatization with (R, S)-FDPEA is much easier than with a conventional reagent. (2) The conformation of the resulting FDPEA derivative is definitely fixed by the characteristic hydrogen bonding and arrangement of related functional groups, so that the Δδ values determined by (R, S)-FDPEA method are larger than those obtained by conventional method. (3) The fixed conformation can be easily confirmed using UV and NOE difference spectra. In addition, the obtained results can also support the fact that a primary amino compound derivatized with FDLA or FDPEA has the definite conformation shown in Fig. 1.
天然有機化合物討論会の論文
1998-08-31

65(P33) 一級アミノ化合物の絶対配置決定のためのキラル異方性試薬の開発(ポスター発表の部)

スポンサーリンク

概要

著者

関連論文

スポンサーリンク