4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Chloride as an Enantioseparation Enhancer for Chiral Derivatization-LC Analysis of D- and L-Amino acids

Kenichiro TODOROKI; Misuzu NAKAMURA; Yuhi SATO; Kanoko GOTO; Tatsuki NAKANO; Yasuhiro ISHII; Jun Zhe MIN; Koichi INOUE; Toshimasa TOYO’OKA

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4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Chloride as an Enantioseparation Enhancer for Chiral Derivatization-LC Analysis of D- and L-Amino acids

机译：4-（4,6-二甲氧基-1,3,5-三嗪-2-基）-4-甲基吗啉鎓盐作为对映体分离增强剂，用于D-和L-氨基酸的手性衍生化-LC分析

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We have developed a high-resolution chiral derivatization-LC method for the determination of D- and L-amino acids using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as an enantioseparation enhancer. In this method, D- and L-amino acids were derivatized with (S )-(-)-1-(naphthyl)ethylamine (NEA) in the presence of DMT-MM as a condensing agent. These conditions resulted in the amino group of the D- and L-amino acid-NEA derivative being introduced in the triazine unit of DMT-MM, producing sterically bulky diastereoisomers. The resulting derivatives of the D- and L-amino acids could be discriminated and successfully enantioseparated through reversed-phase LC. This enantioseparation enhancement effect was demonstrated when using six other commercially available chiral amines as derivatization reagents. Since triazine modification possesses high ESI-responsivity, they showed higher sensitivities than non-triazine derivatives. The developed derivatization method was successfully applied to highly sensitive quantification of D- and L-amino acids by combining LC-MS/MS analysis.

机译：我们已经开发了一种高分辨率的手性衍生化LC方法，用于使用4-（4,6-二甲氧基-1,3,5-三嗪-2-基）-4-甲基吗啉鎓氯化物测定D-和L-氨基酸（DMT-MM）作为对映体分离增强剂。在该方法中，在作为缩合剂的DMT-MM的存在下，将（-S）-（-）-1-（萘基）乙胺（NEA）衍生化D-和L-氨基酸。这些条件导致D-和L-氨基酸-NEA衍生物的氨基被引入DMT-MM的三嗪单元中，产生空间上庞大的非对映异构体。 D-和L-氨基酸的衍生物可以通过反相LC进行区分并成功地对映分离。当使用其他六种可商购的手性胺作为衍生试剂时，证明了这种对映异构体增强作用。由于三嗪改性具有高ESI响应性，因此与非三嗪衍生物相比，它们显示出更高的灵敏度。通过结合LC-MS / MS分析，开发的衍生化方法成功地应用于D-和L-氨基酸的高灵敏度定量。

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《CHROMATOGRAPHY》 |2016年第1期|共6页
作者
Kenichiro TODOROKI; Misuzu NAKAMURA; Yuhi SATO; Kanoko GOTO; Tatsuki NAKANO; Yasuhiro ISHII; Jun Zhe MIN; Koichi INOUE; Toshimasa TOYO’OKA;
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中图分类化学;
关键词
DMT-MMD- and L-Amino acidChiral derivatizationEnantioseparation enhancer;

机译：DMT-MMD-和L-氨基酸手性衍生对映体分离增强剂;

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1. 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride as an enantioseparation enhancer for fluorescence chiral derivatization-liquid chromatographic analysis of DL-lactic acid [J] . Kenichiro Todoroki, Kanoko Goto, Tatsuki Nakano, Journal of chromatography, A: Including electrophoresis and other separation methods . 2014,第Null期

机译：4-（4,6-二甲氧基-1,3,5-三嗪-2-基）-4-甲基吗啉鎓氯化物作为对映体分离增强剂，用于DL-乳酸的荧光手性衍生化-液相色谱分析
2. An Easy and Convenient Synthesis of beta-Lactams via a One-Pot Staudinger Reaction with 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Chloride Starting from Substituted Carboxylic Acids [J] . Zarei Maaroof Letters in organic chemistry . 2015,第1期

机译：通过一锅Staudinger反应与取代的羧酸开始的4-（4,6-二甲氧基-1,3,5-三嗪-2-基）-4-甲基吗啉鎓盐的一锅Staudinger反应轻松合成β-内酰胺
3. Enhancing hyaluronan pseudoplasticity via 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride-mediated conjugation with short alkyl moieties [J] . Petta Dalila, Eglin David, Grijpma Dirk W., Carbohydrate Polymers: Scientific and Technological Aspects of Industrially Important Polysaccharides . 2016,第Null期

机译：通过4-（4,6-二甲氧基-1,3,5-三嗪-2-基）-4-甲基吗啉氯化物介导的短烷基部分缀合增强透明质酸假塑性
4. Enantioseparation of acidic chiral compounds on cellulosetris(3,5-dimethylphenylcarbamate) chiral stationary phase by HPLC [C] . (missing) International Beijing conference and exhibition on instrumental analysis . 2003

机译：HPLC对纤维素骨（3,5-二甲基苯胺酸盐）手性固定相的酸性手性化合物的映对分析
5. Distribution of water around L-amino acid side chains: Computational and statistical analysis. [D] . Lai, Ricky Hai. 2008

机译：L-氨基酸侧链周围的水分布：计算和统计分析。
6. Demonstration of Imino Acids as Products of the Reactions Catalyzed by D- and L-Amino Acid Oxidases [O] . Edmund W. Hafner, Daniel Wellner 1971

机译：展示作为D-和L-氨基酸氧化酶催化反应产物的氨基酸
7. 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Chloride as an Enantioseparation Enhancer for Chiral Derivatization-LC Analysis of D- and L-Amino acids [O] . Kenichiro TODOROKI, Misuzu NAKAMURA, Yuhi SATO, 2016

机译：4-（4,6-二甲氧基-1,3,5-三嗪-2-基）-4-甲基卟啉氯化物作为对映衍生化-LC分析的映对增强剂，对D-和L-氨基酸分析
8. Results of a Guinea Pig Sensitization Study and a Human Repeat Insult Patch Test with Sandospace S: Benzenesulfonic Acid, 4-((4-chloro-6-(1-methylethoxy)- l,3,5-triazin-2-yl)amino)-, sodium salt (1:1). [R] . 2009

机译：豚鼠致敏试验结果和人类重复损伤试验用sandospace s：苯磺酸，4 - （（4-氯-6-（1-甲基乙氧基）-1,3,5-三嗪-2-基）氨基） - ，钠盐（1：1）。

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Chloride as an Enantioseparation Enhancer for Chiral Derivatization-LC Analysis of D- and L-Amino acids

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