tetrahydrofolate (BioDeep_00000229169)

 

Secondary id: BioDeep_00000004381, BioDeep_00001868885

human metabolite PANOMIX_OTCML-2023 Chemicals and Drugs BioNovoGene_Lab2019


代谢物信息卡片


(2S)-2-[(4-{[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

化学式: C19H23N7O6 (445.171)
中文名称: 四氢叶酸
谱图信息: 最多检出来源 Homo sapiens(blood) 28.52%

分子结构信息

SMILES: C1C(NC2=C(N1)N=C(NC2=O)N)CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O
InChI: InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11-,12-/m0/s1

描述信息

Tetrahydrofolic acid, also known as (6s)-tetrahydrofolate or (6s)-thfa, belongs to glutamic acid and derivatives class of compounds. Those are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Tetrahydrofolic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Tetrahydrofolic acid can be found in a number of food items such as malabar plum, parsnip, white lupine, and alpine sweetvetch, which makes tetrahydrofolic acid a potential biomarker for the consumption of these food products. Tetrahydrofolic acid may be a unique S.cerevisiae (yeast) metabolite. Tetrahydrofolic acid is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Tetrahydrofolate is transported across cells by receptor-mediated endocytosis where it is needed to maintain normal erythropoiesis, synthesize purine and thymidylate nucleic acids, interconvert amino acids, methylate tRNA, and generate and use formate (DrugBank).
COVID info from COVID-19 Disease Map
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS

同义名列表

17 个代谢物同义名

(2S)-2-[(4-{[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid; 5,6,7,8-Tetrahydrofolic acid, ion (2-)-isomer; 5,6,7,8-Tetrahydrofolic acid, (D-(-))-isomer; 5,6,7,8-Tetrahydrofolic acid, (L)-isomer; L-5,6,7,8-Tetrahydrofolic acid; (6S)-5,6,7,8-Tetrahydrofolate; 5,6,7,8-Tetrahydrofolic acid; Tetrahydropteroylglutamate; (6S)-Tetrahydrofolic acid; 5,6,7,8-Tetrahydrofolate; (6S)-Tetrahydrofolate; tetrahydrofolic acid; Tetrahydrofolate; (6S)-THFA; THFA; THF; Tetrahydrofolate



数据库引用编号

23 个数据库交叉引用编号

分类词条

2 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。

亚细胞结构定位 关联基因列表
Cytoplasm 9 ALB, CCND1, DHFR, DHPS, DMGDH, FPGS, FTCD, MTHFD1, TYMS
Peripheral membrane protein 1 HSD17B6
Nucleus 4 ALB, CCND1, GGH, TYMS
cytosol 11 ALB, CCND1, DHFR, DHPS, FPGS, FTCD, GART, KRT83, MTHFD1, MTHFD1L, TYMS
centrosome 2 ALB, CCND1
nucleoplasm 1 CCND1
Cell membrane 1 SCN2A
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 1 SCN2A
glutamatergic synapse 1 SCN2A
Golgi apparatus 2 ALB, FTCD
Golgi membrane 1 FTCD
mitochondrial inner membrane 2 FPGS, TYMS
presynaptic membrane 1 SCN2A
Cytoplasm, cytosol 1 FTCD
Lysosome 1 GGH
plasma membrane 2 FTCD, SCN2A
Membrane 3 MTHFD1, MTHFD1L, SCN2A
axon 1 SCN2A
extracellular exosome 6 ALB, FTCD, GART, GGH, MTHFD1, SPINK1
Lumenal side 1 HSD17B6
endoplasmic reticulum 3 ALB, FTCD, HSD17B6
extracellular space 3 ALB, GGH, KRT83
bicellular tight junction 1 CCND1
intercalated disc 1 SCN2A
mitochondrion 6 DHFR, DMGDH, FPGS, MTHFD1, MTHFD1L, TYMS
protein-containing complex 1 ALB
intracellular membrane-bounded organelle 1 HSD17B6
Microsome membrane 1 HSD17B6
Secreted 2 ALB, SPINK1
extracellular region 2 ALB, GGH
Mitochondrion matrix 2 FPGS, TYMS
mitochondrial matrix 4 DMGDH, FPGS, MTHFD1L, TYMS
anchoring junction 1 ALB
Nucleus membrane 1 CCND1
nuclear membrane 1 CCND1
T-tubule 1 SCN2A
Mitochondrion inner membrane 1 TYMS
ciliary basal body 1 ALB
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome, centriole 1 FTCD
centriole 2 ALB, FTCD
Secreted, extracellular space 1 GGH
spindle pole 1 ALB
blood microparticle 1 ALB
Melanosome 1 GGH
Smooth endoplasmic reticulum membrane 1 FTCD
endoplasmic reticulum lumen 1 ALB
transcription repressor complex 1 CCND1
platelet alpha granule lumen 1 ALB
specific granule lumen 1 GGH
tertiary granule lumen 1 GGH
node of Ranvier 1 SCN2A
paranode region of axon 1 SCN2A
azurophil granule lumen 1 GGH
[Isoform 2]: Cytoplasm 1 FPGS
Vacuole 1 GGH
endoplasmic reticulum-Golgi intermediate compartment 1 FTCD
keratin filament 1 KRT83
voltage-gated sodium channel complex 1 SCN2A
cyclin-dependent protein kinase holoenzyme complex 1 CCND1
cyclin D1-CDK4 complex 1 CCND1
cyclin D1-CDK6 complex 1 CCND1
ciliary transition fiber 1 ALB
[Isoform 1]: Mitochondrion inner membrane 1 FPGS


文献列表

  • Minmin Zhang, Guangfeng Liu, Yunlong Zhang, Ting Chen, Shanshan Feng, Rujie Cai, Changrui Lu. The Second Class of Tetrahydrofolate (THF-II) Riboswitches Recognizes the Tetrahydrofolic Acid Ligand via Local Conformation Changes. International journal of molecular sciences. 2022 May; 23(11):. doi: 10.3390/ijms23115903. [PMID: 35682583]
  • Naveen Kr Dubey. Sensitive and rapid simultaneous quantitation of leucovorin and its major active metabolite 5-methyl-tetrahydrofolate in human plasma using a liquid chromatography coupled with triple quadruple mass spectrometry. Biomedical chromatography : BMC. 2022 Apr; 36(4):e5299. doi: 10.1002/bmc.5299. [PMID: 34913177]
  • Shaimaa M Sallam, Eman Shawky, Samah M El Sohafy. Determination of the effect of germination on the folate content of the seeds of some legumes using HPTLC-mass spectrometry-multivariate image analysis. Food chemistry. 2021 Nov; 362(?):130206. doi: 10.1016/j.foodchem.2021.130206. [PMID: 34082289]
  • Natalia I Krupenko, Jaspreet Sharma, Peter Pediaditakis, Kristi L Helke, Madeline S Hall, Xiuxia Du, Susan Sumner, Sergey A Krupenko. Aldh1l2 knockout mouse metabolomics links the loss of the mitochondrial folate enzyme to deregulation of a lipid metabolism observed in rare human disorder. Human genomics. 2020 11; 14(1):41. doi: 10.1186/s40246-020-00291-3. [PMID: 33168096]
  • Weimin Wang, Haibo Wang, Liangliang Xiang, Tengyang Ni, Feng Jin, Jianliang Deng, Yunlei Zhang, Ishikawa Shintaro, Yan Zhou, Yanqing Liu. DJ‑1 is a new prognostic marker and predicts chemotherapy efficacy in colorectal cancer. Oncology reports. 2020 07; 44(1):77-90. doi: 10.3892/or.2020.7593. [PMID: 32627002]
  • J W McFadden, C L Girard, S Tao, Z Zhou, J K Bernard, M Duplessis, H M White. Symposium review: One-carbon metabolism and methyl donor nutrition in the dairy cow. Journal of dairy science. 2020 Jun; 103(6):5668-5683. doi: 10.3168/jds.2019-17319. [PMID: 32278559]
  • David A Korasick, Pramod K Kandoth, John J Tanner, Melissa G Mitchum, Lesa J Beamer. Impaired folate binding of serine hydroxymethyltransferase 8 from soybean underlies resistance to the soybean cyst nematode. The Journal of biological chemistry. 2020 03; 295(11):3708-3718. doi: 10.1074/jbc.ra119.012256. [PMID: 32014996]
  • Petra Ložnjak, Carolina García-Salinas, Rocío Isabel Díaz de la Garza, Anette Bysted, Jette Jakobsen. The use of a plant enzyme for rapid and sensitive analysis of naturally-occurring folates in food by liquid chromatography-tandem mass spectrometry. Journal of chromatography. A. 2019 Jun; 1594(?):34-44. doi: 10.1016/j.chroma.2019.02.037. [PMID: 30799066]
  • Wenzhu Guo, Tong Lian, Baobao Wang, Jiantao Guan, Dong Yuan, Huan Wang, Fardous Mohammad Safiul Azam, Xing Wan, Weixuan Wang, Qiuju Liang, Haiyang Wang, Jinxing Tu, Chunyi Zhang, Ling Jiang. Genetic mapping of folate QTLs using a segregated population in maize. Journal of integrative plant biology. 2019 Jun; 61(6):675-690. doi: 10.1111/jipb.12811. [PMID: 30938052]
  • Judy R Rees, Carolyn B Morris, Janet L Peacock, Per M Ueland, Elizabeth L Barry, Gail E McKeown-Eyssen, Jane C Figueiredo, Dale C Snover, John A Baron. Unmetabolized Folic Acid, Tetrahydrofolate, and Colorectal Adenoma Risk. Cancer prevention research (Philadelphia, Pa.). 2017 Aug; 10(8):451-458. doi: 10.1158/1940-6207.capr-16-0278. [PMID: 28600398]
  • Noelia Foresi, Martín L Mayta, Anabella F Lodeyro, Denise Scuffi, Natalia Correa-Aragunde, Carlos García-Mata, Claudia Casalongué, Néstor Carrillo, Lorenzo Lamattina. Expression of the tetrahydrofolate-dependent nitric oxide synthase from the green alga Ostreococcus tauri increases tolerance to abiotic stresses and influences stomatal development in Arabidopsis. The Plant journal : for cell and molecular biology. 2015 Jun; 82(5):806-21. doi: 10.1111/tpj.12852. [PMID: 25880454]
  • Yvonne Wettergren, Helena Taflin, Elisabeth Odin, Karl Kodeda, Kristoffer Derwinger. A pharmacokinetic and pharmacodynamic investigation of Modufolin® compared to Isovorin® after single dose intravenous administration to patients with colon cancer: a randomized study. Cancer chemotherapy and pharmacology. 2015 Jan; 75(1):37-47. doi: 10.1007/s00280-014-2611-9. [PMID: 25342290]
  • Jeong-hwa Choi, Zoe Yates, Charlotte Martin, Lyndell Boyd, Xiaowei Ng, Virginia Skinner, Ron Wai, Martin Veysey, Mark Lucock. Gene-Nutrient Interaction between Folate and Dihydrofolate Reductase in Risk for Adenomatous Polyp Occurrence: A Preliminary Report. Journal of nutritional science and vitaminology. 2015; 61(6):455-9. doi: 10.3177/jnsv.61.455. [PMID: 26875486]
  • Patricia Díaz-Hellín, Sergio Gómez-Alonso, Anna Borrull, Nicolas Rozès, Ricardo Cordero-Otero, Juan Úbeda. Membrane lipid variability in Saccharomyces cerevisiae wine strains rehydrated in the presence of metabolic activators. Journal of agricultural and food chemistry. 2014 Aug; 62(34):8679-85. doi: 10.1021/jf500895y. [PMID: 25007414]
  • Fabiola Castorena-Torres, Perla A Ramos-Parra, Rogelio V Hernández-Méndez, Andrés Vargas-García, Gerardo García-Rivas, Rocío I Díaz de la Garza. Natural folates from biofortified tomato and synthetic 5-methyl-tetrahydrofolate display equivalent bioavailability in a murine model. Plant foods for human nutrition (Dordrecht, Netherlands). 2014 Mar; 69(1):57-64. doi: 10.1007/s11130-013-0402-9. [PMID: 24445671]
  • Perla A Ramos-Parra, Carolina García-Salinas, Carmen Hernández-Brenes, Rocío I Díaz de la Garza. Folate levels and polyglutamylation profiles of papaya (Carica papaya cv. Maradol) during fruit development and ripening. Journal of agricultural and food chemistry. 2013 Apr; 61(16):3949-56. doi: 10.1021/jf305364x. [PMID: 23574547]
  • Susanne H Kirsch, Wolfgang Herrmann, Jürgen Geisel, Rima Obeid. Assay of whole blood (6S)-5-CH3-H4folate using ultra performance liquid chromatography tandem mass spectrometry. Analytical and bioanalytical chemistry. 2012 Aug; 404(3):895-902. doi: 10.1007/s00216-012-6180-7. [PMID: 22729356]
  • Rima Obeid, Susanne H Kirsch, Mariz Kasoha, Rudolf Eckert, Wolfgang Herrmann. Concentrations of unmetabolized folic acid and primary folate forms in plasma after folic acid treatment in older adults. Metabolism: clinical and experimental. 2011 May; 60(5):673-80. doi: 10.1016/j.metabol.2010.06.020. [PMID: 20727555]
  • Avinash C Srivastava, Perla A Ramos-Parra, Mohamed Bedair, Ana L Robledo-Hernández, Yuhong Tang, Lloyd W Sumner, Rocío I Díaz de la Garza, Elison B Blancaflor. The folylpolyglutamate synthetase plastidial isoform is required for postembryonic root development in Arabidopsis. Plant physiology. 2011 Mar; 155(3):1237-51. doi: 10.1104/pp.110.168278. [PMID: 21233333]
  • Carolyn M Summers, Laura E Mitchell, Anna Stanislawska-Sachadyn, Shirley F Baido, Ian A Blair, Joan M Von Feldt, Alexander S Whitehead. Genetic and lifestyle variables associated with homocysteine concentrations and the distribution of folate derivatives in healthy premenopausal women. Birth defects research. Part A, Clinical and molecular teratology. 2010 Aug; 88(8):679-88. doi: 10.1002/bdra.20683. [PMID: 20544798]
  • Cullen K T Pang, Joshua H Hunter, Ramesh Gujjar, Ramulu Podutoori, Julie Bowman, Devaraja G Mudeppa, Pradipsinh K Rathod. Catalytic and ligand-binding characteristics of Plasmodium falciparum serine hydroxymethyltransferase. Molecular and biochemical parasitology. 2009 Nov; 168(1):74-83. doi: 10.1016/j.molbiopara.2009.06.011. [PMID: 19591883]
  • Steven W Bailey, June E Ayling. The extremely slow and variable activity of dihydrofolate reductase in human liver and its implications for high folic acid intake. Proceedings of the National Academy of Sciences of the United States of America. 2009 Sep; 106(36):15424-9. doi: 10.1073/pnas.0902072106. [PMID: 19706381]
  • Yong Wang, Hong-Yang Zhang, Qiong-Lin Liang, Hui-Hua Yang, Yi-Ming Wang, Qing-Fei Liu, Ping Hu, Xiao-Ying Zheng, Xin-Ming Song, Gong Chen, Ting Zhang, Jian-Xin Wu, Guo-An Luo. Simultaneous quantification of 11 pivotal metabolites in neural tube defects by HPLC-electrospray tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Feb; 863(1):94-100. doi: 10.1016/j.jchromb.2008.01.010. [PMID: 18243823]
  • M Righetti. [Folate metabolism dysfunction]. Giornale italiano di nefrologia : organo ufficiale della Societa italiana di nefrologia. 2008 Jan; 25(1):32-41. doi: NULL. [PMID: 18264916]
  • Jong-Sik Jin, Yu-Feng Zhao, Norio Nakamura, Teruaki Akao, Nobuko Kakiuchi, Masao Hattori. Isolation and characterization of a human intestinal bacterium, Eubacterium sp. ARC-2, capable of demethylating arctigenin, in the essential metabolic process to enterolactone. Biological & pharmaceutical bulletin. 2007 May; 30(5):904-11. doi: 10.1248/bpb.30.904. [PMID: 17473433]
  • Fabrice Rébeillé, Claude Alban, Jacques Bourguignon, Stéphane Ravanel, Roland Douce. The role of plant mitochondria in the biosynthesis of coenzymes. Photosynthesis research. 2007 May; 92(2):149-62. doi: 10.1007/s11120-007-9167-z. [PMID: 17464574]
  • Sergei Storozhenko, Oscar Navarrete, Stéphane Ravanel, Veerle De Brouwer, Peter Chaerle, Guo-Fang Zhang, Olivier Bastien, Willy Lambert, Fabrice Rébeillé, Dominique Van Der Straeten. Cytosolic hydroxymethyldihydropterin pyrophosphokinase/dihydropteroate synthase from Arabidopsis thaliana: a specific role in early development and stress response. The Journal of biological chemistry. 2007 Apr; 282(14):10749-61. doi: 10.1074/jbc.m701158200. [PMID: 17289662]
  • Dean DellaPenna. Biofortification of plant-based food: enhancing folate levels by metabolic engineering. Proceedings of the National Academy of Sciences of the United States of America. 2007 Mar; 104(10):3675-6. doi: 10.1073/pnas.0700640104. [PMID: 17360411]
  • Ya-Sheng Zhang, Li-Fei Zhu, Xue-Song Weng. [Clinical observation on treatment of gastric cancer with zhijing granules: a report of 148 cases]. Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine. 2006 May; 4(3):315-7. doi: 10.3736/jcim20060320. [PMID: 16696924]
  • T Sahr, S Ravanel, F Rébeillé. Tetrahydrofolate biosynthesis and distribution in higher plants. Biochemical Society transactions. 2005 Aug; 33(Pt 4):758-62. doi: 10.1042/bst0330758. [PMID: 16042593]
  • Johan D M Patring, Jelena A Jastrebova, Sofia B Hjortmo, Thomas A Andlid, I Margaretha Jägerstad. Development of a simplified method for the determination of folates in baker's yeast by HPLC with ultraviolet and fluorescence detection. Journal of agricultural and food chemistry. 2005 Apr; 53(7):2406-11. doi: 10.1021/jf048083g. [PMID: 15796570]
  • Aymeric Goyer, Tanya L Johnson, Laura J Olsen, Eva Collakova, Yair Shachar-Hill, David Rhodes, Andrew D Hanson. Characterization and metabolic function of a peroxisomal sarcosine and pipecolate oxidase from Arabidopsis. The Journal of biological chemistry. 2004 Apr; 279(17):16947-53. doi: 10.1074/jbc.m400071200. [PMID: 14766747]
  • Bashir M Rezk, Guido R M M Haenen, Wim J F van der Vijgh, Aalt Bast. Tetrahydrofolate and 5-methyltetrahydrofolate are folates with high antioxidant activity. Identification of the antioxidant pharmacophore. FEBS letters. 2003 Dec; 555(3):601-5. doi: 10.1016/s0014-5793(03)01358-9. [PMID: 14675781]
  • Marlies K Ozias, Kevin L Schalinske. All-trans-retinoic acid rapidly induces glycine N-methyltransferase in a dose-dependent manner and reduces circulating methionine and homocysteine levels in rats. The Journal of nutrition. 2003 Dec; 133(12):4090-4. doi: 10.1093/jn/133.12.4090. [PMID: 14652353]
  • A F Harper, J W Knight, E Kokue, J L Usry. Plasma reduced folates, reproductive performance, and conceptus development in sows in response to supplementation with oxidized and reduced sources of folic acid. Journal of animal science. 2003 Mar; 81(3):735-44. doi: 10.2527/2003.813735x. [PMID: 12661654]
  • Samuel Jabrin, Stéphane Ravanel, Bernadette Gambonnet, Roland Douce, Fabrice Rébeillé. One-carbon metabolism in plants. Regulation of tetrahydrofolate synthesis during germination and seedling development. Plant physiology. 2003 Mar; 131(3):1431-9. doi: 10.1104/pp.016915. [PMID: 12644692]
  • Andrew D Hanson, Jesse F Gregory. Synthesis and turnover of folates in plants. Current opinion in plant biology. 2002 Jun; 5(3):244-9. doi: 10.1016/s1369-5266(02)00249-2. [PMID: 11960743]
  • François Mesnard, Albrecht Roscher, Andrew P Garlick, Sandrine Girard, Evelyne Baguet, Randolf R J Arroo, Jacques Lebreton, Richard J Robins, GeorgeR Ratcliffe. Evidence for the involvement of tetrahydrofolate in the demethylation of nicotine by Nicotiana plumbaginifolia cell-suspension cultures. Planta. 2002 Apr; 214(6):911-9. doi: 10.1007/s00425-001-0702-4. [PMID: 11941468]
  • S Ravanel, H Cherest, S Jabrin, D Grunwald, Y Surdin-Kerjan, R Douce, F Rébeillé. Tetrahydrofolate biosynthesis in plants: molecular and functional characterization of dihydrofolate synthetase and three isoforms of folylpolyglutamate synthetase in Arabidopsis thaliana. Proceedings of the National Academy of Sciences of the United States of America. 2001 Dec; 98(26):15360-5. doi: 10.1073/pnas.261585098. [PMID: 11752472]
  • R Douce, J Bourguignon, M Neuburger, F Rébeillé. The glycine decarboxylase system: a fascinating complex. Trends in plant science. 2001 Apr; 6(4):167-76. doi: 10.1016/s1360-1385(01)01892-1. [PMID: 11286922]
  • J L Vallet, R K Christenson, H G Klemcke, P L Pearson. Intravenous infusion of iron and tetrahydrofolate does not influence intrauterine uteroferrin and secreted folate-binding protein content in swine. Journal of animal science. 2001 Jan; 79(1):188-92. doi: 10.2527/2001.791188x. [PMID: 11204699]
  • K Nilsson, L Gustafson, B Hultberg. Plasma homocysteine is a sensitive marker for tissue deficiency of both cobalamines and folates in a psychogeriatric population. Dementia and geriatric cognitive disorders. 1999 Nov; 10(6):476-82. doi: 10.1159/000017193. [PMID: 10559563]
  • E J Kim, N S Kim, G M Lee. Development of a serum-free medium for the production of humanized antibody from Chinese hamster ovary cells using a statistical design. In vitro cellular & developmental biology. Animal. 1998 Nov; 34(10):757-61. doi: 10.1007/s11626-998-0029-6. [PMID: 9870524]
  • V Prabhu, K B Chatson, H Lui, G D Abrams, J King. Effects of sulfanilamide and methotrexate on 13C fluxes through the glycine decarboxylase/serine hydroxymethyltransferase enzyme system in arabidopsis. Plant physiology. 1998 Jan; 116(1):137-44. doi: 10.1104/pp.116.1.137. [PMID: 9449840]
  • L Hullán, L Trézl, T Szarvas, A Csiba. The hydrazine derivative aminoguanidine inhibits the reaction of tetrahydrofolic acid with hydroxymethylarginine biomolecule. Acta biologica Hungarica. 1998; 49(2-4):265-73. doi: NULL. [PMID: 10526969]
  • E Odin, G Carlsson, R Frösing, B Gustavsson, C P Spears, P A Larsson. Chemical stability and human plasma pharmacokinetics of reduced folates. Cancer investigation. 1998; 16(7):447-55. doi: 10.3109/07357909809011698. [PMID: 9774951]
  • D W Kim, S Delle Fratte, S S Jeong, V Schirch. Determination of serine hydroxymethyltransferase and reduced folate pools in tissue extracts. Analytical biochemistry. 1997 Nov; 253(2):201-9. doi: 10.1006/abio.1997.2388. [PMID: 9367504]
  • L T Vahteristo, V Ollilainen, P Varo. Liquid chromatographic determination of folate monoglutamates in fish, meat, egg, and dairy products consumed in Finland. Journal of AOAC International. 1997 Mar; 80(2):373-8. doi: 10.1093/jaoac/80.2.373. [PMID: 9086593]
  • K Sasaki, M Natsuhori, M Shimoda, Y Saima, E Kokue. Role of high-affinity folate-binding protein in the plasma distribution of tetrahydrofolate in pigs. The American journal of physiology. 1996 Jan; 270(1 Pt 2):R105-10. doi: 10.1152/ajpregu.1996.270.1.r105. [PMID: 8769791]
  • M Natsuhori, M Shimoda, E Kokue. Alteration of plasma folates in gestating sows and newborn piglets. The American journal of physiology. 1996 Jan; 270(1 Pt 2):R99-104. doi: 10.1152/ajpregu.1996.270.1.r99. [PMID: 8769790]
  • T Hashimoto, K Omura, T Sunohara, A Osari, T Yasuda, K Kawakami, T Matsu, F Ishida, Y Watanabe, M Fukushima. [Pharmacokinetics and changes of reduced folate levels in tumor after administration of cisplatin]. Gan to kagaku ryoho. Cancer & chemotherapy. 1994 May; 21(6):859-64. doi: NULL. [PMID: 8185345]
  • J J McGuire, K J Heitzman, W H Haile, C A Russell, D E McCloskey, J R Piper. Cross-resistance studies of folylpolyglutamate synthetase-deficient, methotrexate-resistant CCRF-CEM human leukemia sublines. Leukemia. 1993 Dec; 7(12):1996-2003. doi: . [PMID: 8255099]
  • H Müller. [The determination of the folic acid content of foods of animal origin using high performance liquid chromatography (HPLC)]. Zeitschrift fur Lebensmittel-Untersuchung und -Forschung. 1993 Jun; 196(6):518-21. doi: 10.1007/bf01201330. [PMID: 8328216]
  • K Sasaki, M Shimoda, Y Aoki, M Natsuhori, E Kokue. Contribution of plasma protein binding to the stability of tetrahydrofolate in pig plasma. Advances in experimental medicine and biology. 1993; 338(?):749-52. doi: 10.1007/978-1-4615-2960-6_156. [PMID: 8304221]
  • M Natsuhori, E Kokue, M Shimoda. Influence of gestation and lactation on the levels of plasma folates in sows. Advances in experimental medicine and biology. 1993; 338(?):733-6. doi: 10.1007/978-1-4615-2960-6_152. [PMID: 8304217]
  • L H Matherly, S M Angeles, C A Czajkowski. Characterization of transport-mediated methotrexate resistance in human tumor cells with antibodies to the membrane carrier for methotrexate and tetrahydrofolate cofactors. The Journal of biological chemistry. 1992 Nov; 267(32):23253-60. doi: 10.1016/s0021-9258(18)50084-3. [PMID: 1429671]
  • M Shimoda. Simultaneous determination of tetrahydrofolate and N5-methyltetrahydrofolate in pig plasma by high-performance liquid chromatography with electrochemical detection. The Journal of veterinary medical science. 1992 Apr; 54(2):249-53. doi: 10.1292/jvms.54.249. [PMID: 1606254]
  • D G Priest, J C Schmitz, M A Bunni, R K Stuart. Pharmacokinetics of leucovorin metabolites in human plasma as a function of dose administered orally and intravenously. Journal of the National Cancer Institute. 1991 Dec; 83(24):1806-12. doi: 10.1093/jnci/83.24.1806. [PMID: 1744924]
  • M Natsuhori, M Shimoda, E Kokue, T Hayama, Y Takahashi. Tetrahydrofolic acid as the principal congener of plasma folates in pigs. The American journal of physiology. 1991 Jul; 261(1 Pt 2):R82-6. doi: 10.1152/ajpregu.1991.261.1.r82. [PMID: 1858958]
  • J Bourguignon, M Neuburger, R Douce. Resolution and characterization of the glycine-cleavage reaction in pea leaf mitochondria. Properties of the forward reaction catalysed by glycine decarboxylase and serine hydroxymethyltransferase. The Biochemical journal. 1988 Oct; 255(1):169-78. doi: 10.1042/bj2550169. [PMID: 3143355]
  • M Marchetti. [Folate determination in serum for clinical use (author's transl)]. Acta vitaminologica et enzymologica. 1981; 3(2):115-25. doi: . [PMID: 6798851]
  • E H BYERS, J STEWART, T J BOND. Enzymic conversion of tetrahydrofolic acid to folinic acid by plant protein. Nature. 1961 Jul; 191(?):179-80. doi: 10.1038/191179a0. [PMID: 13689562]