L-2-Amino-3-(oxalylamino)propanoic acid (BioDeep_00000000206)
Secondary id: BioDeep_00000024498, BioDeep_00000622090, BioDeep_00001867474
human metabolite PANOMIX_OTCML-2023 Endogenous
代谢物信息卡片
N-Oxalyl-L-alpha-beta-diaminopropionic acid (BOAA,ODAP)
化学式: C5H8N2O5 (176.0433)
中文名称: 三七素
谱图信息:
最多检出来源 Chinese Herbal Medicine(otcml) 47.2%
分子结构信息
SMILES: C(C(C(=O)O)N)NC(=O)C(=O)O
InChI: InChI=1S/C5H8N2O5/c6-2(4(9)10)1-7-3(8)5(11)12/h2H,1,6H2,(H,7,8)(H,9,10)(H,11,12)
描述信息
L-2-Amino-3-(oxalylamino)propanoic acid is found in grass pea. L-2-Amino-3-(oxalylamino)propanoic acid is isolated from Panax notoginseng (sanchi
Isolated from Panax notoginseng (sanchi). L-2-Amino-3-(oxalylamino)propanoic acid is found in tea and grass pea.
L-2-Amino-3-(oxalylamino)propanoic acid is an alpha-amino acid.
N(3)-oxalyl-L-2,3-diaminopropionic acid is an N(beta)-acyl-L-2,3-diaminopropionic acid in which the acyl group is oxalyl. It is functionally related to a propionic acid. It is a conjugate acid of a N(3)-(carboxylatoformyl)-L-2,3-diaminopropionate(1-).
Dencichin is a natural product found in Lathyrus latifolius and Lathyrus sativus with data available.
See also: Panax notoginseng root (part of).
Dencichin is a non-protein amino acid originally extracted from Panax notoginseng, and can inhibit HIF-prolyl hydroxylase-2 (PHD-2) activity.
同义名列表
78 个代谢物同义名
(S)-2-Amino-3-(carboxyformamido)propanoic acid; L-alpha-Amino-gamma-oxalylaminopropionic acid; L-alpha-Amino-beta-oxalylaminopropionic acid; oxalyldiaminopropionic acid, (L-Ala)-isomer; 2-Amino-3-(carboxyformamido)propanoic acid; 2-AMINO-3-(CARBOXYFORMAMIDO)PROPANOICACID; L-2-Amino-3-(oxalylamino)propanoic acid; (2-amino-2-carboxymethyl)-L-oxamic acid; Oxamic acid, (2-amino-2-carboxyethyl)-; 2-Amino-3-(carboxyformamido)propanoate; 3-((CARBOXYCARBONYL)AMINO)ALANINE, DL-; 3-amino-N-(carboxycarbonyl)-DL-alanine; beta-N-oxalylaminoalanine, (L)-isomer; Alanine, 3-((carboxycarbonyl)amino)-; 2-amino-3-(oxaloamino)propanoic acid; 3-oxalylamino-2-aminopropionic acid; L-2-Amino-3-(oxalylamino)propanoate; 2-oxalylamino-3-aminopropionic acid; (2-amino-2-carboxyethyl)oxamic acid; 3-amino-N-(carboxycarbonyl)alanine; N3-Oxalyl-L-2,3-diaminopropanoate; 3-((Carboxycarbonyl)amino)alanine; carboxycarbonyl-aminoalanine; beta-N-oxalylamino-L-alanine; NEEQFPMRODQIKX-UHFFFAOYSA-N; oxalyldiaminopropionic acid; .BETA.-(OXALYLAMINO)ALANINE; beta-N-oxalylaminoalanine; beta-(Oxalylamino)alanine; lathyrus neurotoxin; oxalylaminoalanine; (Rac)-Dencichine; UNII-1TG777QI25; (Rac)-Dencichin; dencichin, DL-; DL-dencichin; 1TG777QI25; dencichine; Dencichin; L-BOAA; ODAP; BOAA; N-Oxalyl-L-alpha-beta-diaminopropionic acid (BOAA,ODAP); (2S)-2-amino-3-[(carboxycarbonyl)amino]propanoic acid; (2S)-2-amino-3-((carboxycarbonyl)amino)propanoic acid; beta-N-oxalyl-l-alpha,beta-diaminopropanoic acid; (S)-beta-Oxalyl-alpha,beta-diaminopropionic acid; beta-N-Oxalyl-L-alpha,beta-diaminopropionic acid; beta-N-Oxalo-L-alpha,beta-diaminopropionic acid; (2S)-2-amino-3-(carboxyformamido)propanoic acid; beta-N-Oxalo-L-alpha,eta-diaminopropionic acid; beta-N-Oxalyl-L-alpha,beta-diaminopropionate; OXAMIC ACID, (2-AMINO-2-CARBOXYETHYL)-, L-; (2S)-2-amino-3-(oxaloamino)propanoic acid; N(3)-oxalyl-L-2,3-diaminopropionic acid; (2-Amino-2-carboxyethyl)-L-oxamic acid; 3-N-Oxalyl-L-2,3-diaminopropanoic acid; L-Alanine, 3-((carboxycarbonyl)amino)-; 3-N-Oxalyl-L-2,3-diaminopropionic acid; 3-((CARBOXYCARBONYL)AMINO)ALANINE, L-; 3-N-OXALYL-L-2,3-DIAMINOPROPANOICACID; L-3-Oxalylamino-2-aminopropionic acid; 3-[(Carboxycarbonyl)amino]-L-alanine; 3-((Carboxycarbonyl)amino)-L-alanine; 3-(Carboxycarbonylamino)-L-alanine; 3-[(carboxycarbonyl)amino]alanine; Neurotoxin (Lathyrus sativus); N.BETA.-OXALYLAMINO-L-ALANINE; Nbeta-Oxalylamino-L-alanine; beta-ODAP, >=98\\% (HPLC); 3-(Oxaloamino)alanine; UNII-O8VT5BZ48B; L-Dencichin; | cent-odap; O8VT5BZ48B; beta-ODAP; Ox-Dapro; 3-(Carboxycarbonylamino)-L-alanine
数据库引用编号
28 个数据库交叉引用编号
- ChEBI: CHEBI:173808
- ChEBI: CHEBI:16399
- KEGG: C04209
- PubChem: 440259
- PubChem: 2360
- HMDB: HMDB0029402
- Metlin: METLIN66139
- ChEMBL: CHEMBL5184064
- MeSH: oxalyldiaminopropionic acid
- ChemIDplus: 0007554907
- ChemIDplus: 0005302454
- KNApSAcK: C00001339
- foodb: FDB000491
- chemspider: 2270
- chemspider: 389238
- CAS: 5302-45-4
- CAS: 7554-90-7
- medchemexpress: HY-N6030
- medchemexpress: HY-N1477
- PMhub: MS000018250
- PubChem: 6882
- 3DMET: B00693
- NIKKAJI: J356.641B
- KNApSAcK: 16399
- LOTUS: LTS0085766
- wikidata: Q409824
- LOTUS: LTS0142657
- wikidata: Q27252869
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
5 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Dan Huang, Xin Wang, Wei-Bing Liu, Bang-Ce Ye. Remodeling metabolism of Corynebacterium glutamicum for high-level dencichine production.
Bioresource technology.
2023 Nov; 388(?):129800. doi:
10.1016/j.biortech.2023.129800. [PMID: 37748563] - Yu Sui, Xiaojiang Duan, Jingming Zhang, Yingming Chu, Xing Yang. Synthesis and characterization of a novel 68Ga-labeled p-bromobenzyl lysine-urea-ODAP PSMA inhibitor.
Bioorganic & medicinal chemistry letters.
2023 07; 91(?):129382. doi:
10.1016/j.bmcl.2023.129382. [PMID: 37348571] - Rym Boulfekhar, Leanne Ohlund, Kathrina Mae Kumaresan, Meriem Megoura, Thomas D Warkentin, Pompilia Ispas-Szabo, Lekha Sleno, Mircea Alexandru Mateescu. Diamine Oxidase as a Therapeutic Enzyme: Study of Germination from Vegetal Sources and Investigation of the Presence of β-N-Oxalyl-L-α,β-diaminopropionic Acid (β-ODAP) Using LC-MS/MS.
International journal of molecular sciences.
2023 Feb; 24(5):. doi:
10.3390/ijms24054625. [PMID: 36902055] - Anne Edwards, Isaac Njaci, Abhimanyu Sarkar, Zhouqian Jiang, Gemy George Kaithakottil, Christopher Moore, Jitender Cheema, Clare E M Stevenson, Martin Rejzek, Petr Novák, Marielle Vigouroux, Martin Vickers, Roland H M Wouters, Pirita Paajanen, Burkhard Steuernagel, Jonathan D Moore, Janet Higgins, David Swarbreck, Stefan Martens, Colin Y Kim, Jing-Ke Weng, Sagadevan Mundree, Benjamin Kilian, Shiv Kumar, Matt Loose, Levi Yant, Jiří Macas, Trevor L Wang, Cathie Martin, Peter M F Emmrich. Genomics and biochemical analyses reveal a metabolon key to β-L-ODAP biosynthesis in Lathyrus sativus.
Nature communications.
2023 Feb; 14(1):876. doi:
10.1038/s41467-023-36503-2. [PMID: 36797319] - Wenna Li, Zhao Zhou, Xianglai Li, Lin Ma, Qingyuan Guan, Guojun Zheng, Hao Liang, Yajun Yan, Xiaolin Shen, Jia Wang, Xinxiao Sun, Qipeng Yuan. Biosynthesis of plant hemostatic dencichine in Escherichia coli.
Nature communications.
2022 09; 13(1):5492. doi:
10.1038/s41467-022-33255-3. [PMID: 36123371] - Moshe Goldsmith, Shiri Barad, Maor Knafo, Alon Savidor, Shifra Ben-Dor, Alexander Brandis, Tevie Mehlman, Yoav Peleg, Shira Albeck, Orly Dym, Efrat Ben-Zeev, Ranjit S Barbole, Asaph Aharoni, Ziv Reich. Identification and characterization of the key enzyme in the biosynthesis of the neurotoxin β-ODAP in grass pea.
The Journal of biological chemistry.
2022 05; 298(5):101806. doi:
10.1016/j.jbc.2022.101806. [PMID: 35271851] - Zijiang Yang, Guanze Liu, Guanghui Zhang, Jing Yan, Yang Dong, Yingchun Lu, Wei Fan, Bing Hao, Yuan Lin, Ying Li, Xuejiao Li, Qingyan Tang, Guisheng Xiang, Simei He, Junwen Chen, Wei Chen, Zhongping Xu, Zichao Mao, Shengchang Duan, Shuangxia Jin, Shengchao Yang. The chromosome-scale high-quality genome assembly of Panax notoginseng provides insight into dencichine biosynthesis.
Plant biotechnology journal.
2021 05; 19(5):869-871. doi:
10.1111/pbi.13558. [PMID: 33529371] - Chao Huang, Lijing Cheng, Xinyan Feng, Xiaojun Li, Lihua Wang. Dencichine ameliorates renal injury by improving oxidative stress, apoptosis and fibrosis in diabetic rats.
Life sciences.
2020 Oct; 258(?):118146. doi:
10.1016/j.lfs.2020.118146. [PMID: 32721462] - Yan-Hai Zhang, Yuan-Gui Yang, Lei Shi, Yan Jin, Zheng-Tao Wang. [Fingerprinting analysis of non-saponins from water-soluble part and determination of dencichine from Panax notoginseng, P. ginseng and P. quinquefolium based on liquid chromatography coupled with charged aerosol detection].
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.
2020 Jul; 45(14):3475-3480. doi:
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Analytical biochemistry.
2020 02; 591(?):113544. doi:
10.1016/j.ab.2019.113544. [PMID: 31866288] - Peter M F Emmrich, Martin Rejzek, Lionel Hill, Paul Brett, Anne Edwards, Abhimanyu Sarkar, Rob A Field, Cathie Martin, Trevor L Wang. Linking a rapid throughput plate-assay with high-sensitivity stable-isotope label LCMS quantification permits the identification and characterisation of low β-L-ODAP grass pea lines.
BMC plant biology.
2019 Nov; 19(1):489. doi:
10.1186/s12870-019-2091-5. [PMID: 31718544] - Kimino Minagawa, Shin-Ichi Yamada, Ayano Suzuki, Saeko Ta, Toshio Kumai, Fernand Lambein, Kuniko Kusama-Eguchi. Stress-related over-enhancement of the hypothalamic-pituitary-adrenal axis causes experimental neurolathyrism in rats.
Environmental toxicology and pharmacology.
2019 Nov; 72(?):103245. doi:
10.1016/j.etap.2019.103245. [PMID: 31499324] - Veerababu Nagati, Monika Kallubai, Dinesh Kumar Chinthapalli, Rajagopal Subramanyam. Exploration of binding studies of β-oxalyldiamino propionic acid (β-ODAP), a non-protein amino acid with human serum albumin-biophysical and computational approach.
Journal of biomolecular structure & dynamics.
2019 09; 37(15):3914-3922. doi:
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Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2019 Jun; 114(?):108801. doi:
10.1016/j.biopha.2019.108801. [PMID: 30928803] - Fengjuan Liu, Chengjin Jiao, Chunxiao Bi, Quanle Xu, Peng Chen, Adam L Heuberger, Hari B Krishnan. Metabolomics Approach To Understand Mechanisms of β-N-Oxalyl-l-α,β-diaminopropionic Acid (β-ODAP) Biosynthesis in Grass Pea (Lathyrus sativus L.).
Journal of agricultural and food chemistry.
2017 Nov; 65(47):10206-10213. doi:
10.1021/acs.jafc.7b04037. [PMID: 29112818] - Li Jie, Qiu Pengcheng, He Qiaoyan, Bi Linlin, Zhang Meng, Wang Fang, Jia Min, Yan Li, Zhang Ya, Yang Qian, Wang Siwang. Dencichine ameliorates kidney injury in induced type II diabetic nephropathy via the TGF-β/Smad signalling pathway.
European journal of pharmacology.
2017 Oct; 812(?):196-205. doi:
10.1016/j.ejphar.2017.06.024. [PMID: 28633927] - Quanle Xu, Fengjuan Liu, Peng Chen, Joseph M Jez, Hari B Krishnan. β-N-Oxalyl-l-α,β-diaminopropionic Acid (β-ODAP) Content in Lathyrus sativus: The Integration of Nitrogen and Sulfur Metabolism through β-Cyanoalanine Synthase.
International journal of molecular sciences.
2017 Feb; 18(3):. doi:
10.3390/ijms18030526. [PMID: 28264526] - Rui-Yue Tan, Geng-Yan Xing, Guang-Ming Zhou, Feng-Min Li, Wen-Tao Hu, Fernand Lambein, Jun-Lan Xiong, Sheng-Xiang Zhang, Hai-Yan Kong, Hao Zhu, Zhi-Xiao Li, You-Cai Xiong. Plant toxin β-ODAP activates integrin β1 and focal adhesion: A critical pathway to cause neurolathyrism.
Scientific reports.
2017 01; 7(?):40677. doi:
10.1038/srep40677. [PMID: 28094806] - Lin Li, Cheng-xiao Wang, Yuan Qu, Xiu-ming Cui. [Content determination of dencichine in Panax Notoginseng by a reversed phase ion-pair chromatography].
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.
2015 Oct; 40(20):4026-30. doi:
". [PMID: 27062822] - Jun-Lan Xiong, You-Cai Xiong, Xue Bai, Hai-Yan Kong, Rui-Yue Tan, Hao Zhu, Kadambot H M Siddique, Jian-Yong Wang, Neil C Turner. Genotypic Variation in the Concentration of β-N-Oxalyl-L-α,β-diaminopropionic Acid (β-ODAP) in Grass Pea (Lathyrus sativus L.) Seeds Is Associated with an Accumulation of Leaf and Pod β-ODAP during Vegetative and Reproductive Stages at Three Levels of Water Stress.
Journal of agricultural and food chemistry.
2015 Jul; 63(27):6133-41. doi:
10.1021/acs.jafc.5b01729. [PMID: 26027639] - Ling-juan Yang, Cheng-jin Jiao, Er-quan Gao. [Determination of Dencichine and Its Isomer in Panax notoginseng by Pre-column Derivatization HPLC].
Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials.
2015 Feb; 38(2):311-4. doi:
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PloS one.
2015; 10(11):e0140649. doi:
10.1371/journal.pone.0140649. [PMID: 26524073] - E Rivadeneyra-Domínguez, J F Rodríguez-Landa. Cycads and their association with certain neurodegenerative diseases.
Neurologia (Barcelona, Spain).
2014 Nov; 29(9):517-22. doi:
10.1016/j.nrl.2013.03.005. [PMID: 23725821] - Ling-Fang Huang, Hai-Lian Shi, Bo Gao, Hui Wu, Li Yang, Xiao-Jun Wu, Zheng-Tao Wang. Decichine enhances hemostasis of activated platelets via AMPA receptors.
Thrombosis research.
2014 May; 133(5):848-54. doi:
10.1016/j.thromres.2014.02.009. [PMID: 24630643] - Jun-Lan Xiong, Xue Bai, Asfa Batool, Hai-Yan Kong, Rui-Yue Tan, Ya-Fu Wang, Zhi-Xiao Li, You-Cai Xiong. [Ecological function and application of toxin beta-ODAP in grass pea (Lathyrus sativus)].
Ying yong sheng tai xue bao = The journal of applied ecology.
2014 Apr; 25(4):1197-205. doi:
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Food chemistry.
2014 Jan; 143(?):277-81. doi:
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Biochimica et biophysica acta.
2012 Jul; 1818(7):1663-72. doi:
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Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2011 Mar; 49(3):543-9. doi:
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Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2011 Mar; 49(3):556-62. doi:
10.1016/j.fct.2010.05.054. [PMID: 20510333] - Dirk Enneking. The nutritive value of grasspea (Lathyrus sativus) and allied species, their toxicity to animals and the role of malnutrition in neurolathyrism.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2011 Mar; 49(3):694-709. doi:
10.1016/j.fct.2010.11.029. [PMID: 21112364] - Peter B Nunn, James R A Lyddiard, K P W Christopher Perera. Brain glutathione as a target for aetiological factors in neurolathyrism and konzo.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2011 Mar; 49(3):662-7. doi:
10.1016/j.fct.2010.08.037. [PMID: 20816718] - M Van Moorhem, F Lambein, L Leybaert. Unraveling the mechanism of β-N-oxalyl-α,β-diaminopropionic acid (β-ODAP) induced excitotoxicity and oxidative stress, relevance for neurolathyrism prevention.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2011 Mar; 49(3):550-5. doi:
10.1016/j.fct.2010.03.054. [PMID: 20510327] - Kuniko Kusama-Eguchi, Yoshiko Yamazaki, Tadashi Ueda, Atsuhiro Suda, Yukari Hirayama, Fumio Ikegami, Kazuko Watanabe, Mike May, Fernand Lambein, Tadashi Kusama. Hind-limb paraparesis in a rat model for neurolathyrism associated with apoptosis and an impaired vascular endothelial growth factor system in the spinal cord.
The Journal of comparative neurology.
2010 Mar; 518(6):928-42. doi:
10.1002/cne.22257. [PMID: 20058324] - Geeta Mishra, Rakesh Shukla, Mahdi Hasan, Subhash K Khanna, Mukul Das. Potentiation of neurotoxicity of Lathyrus sativus by manganese: alterations in blood-brain barrier permeability.
Toxicology mechanisms and methods.
2009 May; 19(4):318-26. doi:
10.1080/15376510902758947. [PMID: 19778223] - George K Shinomol, Muralidhara. Differential induction of oxidative impairments in brain regions of male mice following subchronic consumption of Khesari dhal (Lathyrus sativus) and detoxified Khesari dhal.
Neurotoxicology.
2007 Jul; 28(4):798-806. doi:
10.1016/j.neuro.2007.03.002. [PMID: 17451808] - Guo-Xiang Xie, Yun-Ping Qiu, Ming-Feng Qiu, Xian-Fu Gao, Yu-Min Liu, Wei Jia. Analysis of dencichine in Panax notoginseng by gas chromatography-mass spectrometry with ethyl chloroformate derivatization.
Journal of pharmaceutical and biomedical analysis.
2007 Feb; 43(3):920-5. doi:
10.1016/j.jpba.2006.09.009. [PMID: 17029672] - Jing Zhu, San-kang Liu, Chun-mei Fu, Zhang-wan Li. [Analysis of dencichine by HPLC with pre-column derivatization].
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.
2006 Nov; 31(22):1865-8. doi:
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Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2006 Aug; 840(2):124-31. doi:
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Plant physiology and biochemistry : PPB.
2006 Feb; 44(2-3):161-9. doi:
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Communications in agricultural and applied biological sciences.
2006; 71(1):79-82. doi:
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Rapid communications in mass spectrometry : RCM.
2005; 19(10):1237-44. doi:
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Clinical biochemistry.
2004 Apr; 37(4):318-22. doi:
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Journal of agricultural and food chemistry.
2003 Jul; 51(16):4617-23. doi:
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Phytochemistry.
2003 Apr; 62(7):1087-91. doi:
10.1016/s0031-9422(02)00658-1. [PMID: 12591261] - Vijayalakshmi Ravindranath. Neurolathyrism: mitochondrial dysfunction in excitotoxicity mediated by L-beta-oxalyl aminoalanine.
Neurochemistry international.
2002 May; 40(6):505-9. doi:
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