Improved and Large-Scale Synthesis of N-methyl-D-aspartic Acid

Xi Liang; Wu Di; Zhu Hong-You; Zhang Cong-Hai; Jin Yi; Lin Jun

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Improved and Large-Scale Synthesis of N-methyl-D-aspartic Acid

机译：改善和大规模合成N-甲基-D-天冬氨酸

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N-Methyl-D-aspartic acid (NMDA) has significant potential as a drug to treat diabetes, Parkinson's and Alzheimer's disease. Consequently, many efforts have been made for synthesis of NMDA, but there exist some flaws yet. In this paper, we report an improved method for Large-Scale Synthesis of optically pure NMDA by Eschweiler-Clarke reaction and deprotection of benzyl by ACE-Cl reagent. The synthesis has been achieved in five steps with an overall yield of 70% and an enantiomeric excess over 99.5%, in particularly, the method avoided the use of toxic methylation reagent. This method can be scaled up to kilogram quantities, providing a solid basis for its further bioactivity studies and drug development.

机译：N-甲基-D-天冬氨酸（NMDA）具有治疗糖尿病，帕金森和阿尔茨海默病的药物的显着潜力。因此，已经为NMDA合成了许多努力，但尚未存在一些缺陷。本文通过Eschweiler-Clarke反应和Ace-Cl试剂的苄基的反应报告了大规模合成光学纯NMDA的改进方法。该合成已经在五个步骤中实现，总收率为70％，对映体过量超过99.5％，特别是该方法避免使用毒性甲基化试剂。该方法可以缩放到千克数量，为其进一步的生物活性研究和药物发育提供坚实的基础。

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来源
《Current Organic Synthesis》 |2015年第2期|共5页
作者
Xi Liang; Wu Di; Zhu Hong-You; Zhang Cong-Hai; Jin Yi; Lin Jun;
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作者单位

Yunnan Univ Sch Chem Sci &

Technol Key Lab Med Chem Nat Resource Minist Educ Kunming 650091 Peoples R China;

Yunnan Univ Sch Chem Sci &

Technol Key Lab Med Chem Nat Resource Minist Educ Kunming 650091 Peoples R China;

Yunnan Univ Sch Chem Sci &

Technol Key Lab Med Chem Nat Resource Minist Educ Kunming 650091 Peoples R China;

Yunnan Univ Sch Chem Sci &

Technol Key Lab Med Chem Nat Resource Minist Educ Kunming 650091 Peoples R China;

Yunnan Univ Sch Chem Sci &

Technol Key Lab Med Chem Nat Resource Minist Educ Kunming 650091 Peoples R China;

Yunnan Univ Sch Chem Sci &

Technol Key Lab Med Chem Nat Resource Minist Educ Kunming 650091 Peoples R China;

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原文格式 PDF
正文语种 eng
中图分类有机化学;
关键词
Eschweiler-Clarke reaction; large-scale; Methylation; reductive amination;

机译：Eschweiler-clarke反应;大规模;甲基化;还原胺化;

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专利

1. Improved and Large-Scale Synthesis of N-methyl-D-aspartic Acid [J] . Xi Liang, Wu Di, Zhu Hong-You, Current Organic Synthesis . 2015,第2期

机译：改善和大规模合成N-甲基-D-天冬氨酸
2. Dopamine D1 receptors co-distribute with N-methyl-D-aspartic acid type-1 subunits and modulate synaptically-evoked N-methyl-D-aspartic acid currents in rat basolateral amygdala. [J] . Pickel VM, Colago EE, Mania I, Neuroscience: An International Journal under the Editorial Direction of IBRO . 2006,第3期

机译：多巴胺D1受体与N-甲基-D-天冬氨酸1型亚基共分布，并在大鼠基底外侧杏仁核中调节突触诱发的N-甲基-D-天冬氨酸电流。
3. Replacement of bovine serum albumin with N-methyl-D-aspartic acid and homocysteine improves development, but not live birth [J] . Spate L. D., Redel B. K., Brown A. N., Molecular reproduction and development . 2012,第5期

机译：用N-甲基-D-天冬氨酸和高半胱氨酸替代牛血清白蛋白可改善发育，但不能活产
4. An efficient method for large-scale synthesis of stereochemically difined and conformationally constrained beta-substituted for alpha,beta-disubstituted amino acids [C] . Xuejun Tang, Vadim A.Soloshonok, Victor J.Hruby the International Peptide Symposium . 2001

机译：大规模合成立体化学差异和构象约束的α，β-二取代的氨基酸的大规模合成的有效方法
5. Differential activation of N-methyl-d-aspartic acid and kainic acid receptors in the pedunculopontine nucleus of the rat modulates both ascending and descending efferent projections related to preattentional and arousal mechanisms. [D] . Huitt, Tiffany Wallace. 2007

机译：大鼠足小神经核中N-甲基-d-天冬氨酸和海藻酸受体的差异激活调节与预注意和唤醒机制有关的上升和下降传出预测。
6. Behavioural and biochemical studies in rats with N-methyl-D-aspartic acid and kainic acid proceedings [O] . R. W. Kerwin, G. P. Luscombe, C. J. Pycock, 1980

机译：N-甲基-D-天冬氨酸和海藻酸对大鼠的行为和生化研究过程
7. Transforming growth factor-Î± attenuates N-methyl-D-aspartic acid toxicity in cortical cultures by preventing protein synthesis inhibition through an Erk1/2-dependent mechanism [O] . Petegnief, Valérie, Friguls, Bibiana, Sanfeliu, Coral, 2015

机译：通过防止蛋白质合成抑制通过Erk1 / 2依赖机制，转化生长因子-α减弱皮质文化中的N-甲基-D-天冬氨酸毒性。
8. Improved Acid Electrolytes-The Synthesis and Structure of Fluorine Containing Sulfonic Acids for Fuel Cells. Final Report July 1987-August 1988 [R] . Gard, G. L. 1988

机译：改进的酸性电解质 - 燃料电池中含氟磺酸的合成和结构。 1987年7月至1988年8月的最终报告

Improved and Large-Scale Synthesis of N-methyl-D-aspartic Acid

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