GDP-L-fucose (BioDeep_00000003567)
Secondary id: BioDeep_00001869070
natural product human metabolite PANOMIX_OTCML-2023 Endogenous
代谢物信息卡片
化学式: C16H25N5O15P2 (589.0822)
中文名称: 5`-二磷酸鸟嘌呤核苷-岩藻糖二钠盐, 5'-二磷酸鸟嘌呤核苷-岩藻糖
谱图信息:
最多检出来源 Chinese Herbal Medicine(otcml) 9.95%
分子结构信息
SMILES: CC1C(C(C(C(O1)OP(=O)(O)OP(=O)(O)OCC2C(C(C(O2)N3C=NC4=C3N=C(NC4=O)N)O)O)O)O)O
InChI: InChI=1S/C16H25N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,7-11,14-15,22-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5+,7+,8+,9+,10+,11-,14+,15+/m0/s1
描述信息
GDP-L-fucose is a sugar nucleotide and a readily available source of fucose. Fucose is a deoxyhexose that is found in nearly all plant and animal species. The monosaccharide plays several important metabolic roles in complex carbohydrates and in glycoproteins. Fucosylated oligosaccharides are involved in cell-cell recognition, selectin-mediated leukocyte-endothelial adhesion, and mouse embryogenesis. They form the basis of the Lewis-type blood group antigens, are involved in the formation of atherosclerosis, and mediate host-bacterial interactions. A decrease in the availability of fucose is associated with leukocyte adhesion deficiency type-II disorder, and fucosylated glycoproteins have been implicated in memory processes. Fucose is made available during the synthesis of fucosylated glycolipids, oligosaccharides, and glycoproteins via a sugar nucleotide intermediate, specifically GDP-L-fucose. GTP-L-fucose pyrophosphorylase (GFPP, E. C. 2.7.7.30) catalyzes the reversible condensation of guanosine triphosphate and beta-L-fucose-1-phosphate to form the nucleotide-sugar GDP-L-fucose. The enzyme functions primarily in the mammalian liver and kidney to salvage free L-fucose during the breakdown of glycolipids and glycoproteins. (PMID: 16086588).
Gdp-l-fucose, also known as gdp fucose or guanosine diphosphate fucose, is a member of the class of compounds known as purine nucleotide sugars. Purine nucleotide sugars are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. Gdp-l-fucose is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Gdp-l-fucose can be found in a number of food items such as breadnut tree seed, okra, pineapple, and pitanga, which makes gdp-l-fucose a potential biomarker for the consumption of these food products. Gdp-l-fucose can be found primarily throughout most human tissues. Gdp-l-fucose exists in all living organisms, ranging from bacteria to humans. In humans, gdp-l-fucose is involved in a couple of metabolic pathways, which include fructose and mannose degradation and fructose intolerance, hereditary. Gdp-l-fucose is also involved in fructosuria, which is a metabolic disorder.
Acquisition and generation of the data is financially supported in part by CREST/JST.
同义名列表
26 个代谢物同义名
[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid; 6-Deoxy-β-L-galactopyranosylguanosine 5-diphosphate; (6-Deoxy-beta-L-galactopyranosyl) ester; Guanosine 5-diphospho-β-L-fucose; Guanosine-5-diphospho-beta-L-fucose; Guanosine 5-diphospho-beta-L-fucose; Guanosine 5’-diphosphate L-fucose; Guanosine 5-diphosphate L-fucose; Diphosphate fucose, guanosine; Guanosine 5’-diphospho-fucose; Fucose, guanosine diphosphate; Guanosine 5-diphospho-fucose; Guanosine 5’-diphosphofucose; Guanosine diphosphate fucose; Guanosine 5-diphosphofucose; Diphosphofucose, guanosine; Guanosine diphosphofucose; GDP-β-L-fucose; GDP-beta-L-Fucose; GDP-Β-L-fucose; GDP-L-fucose; Fucose, GDP; GDP-fucose; GDP Fucose; GDP-Fuc; GDP-fucose
数据库引用编号
29 个数据库交叉引用编号
- ChEBI: CHEBI:13332
- KEGG: C00325
- PubChem: 135402013
- PubChem: 135398655
- PubChem: 10918995
- PubChem: 439211
- HMDB: HMDB0001095
- Metlin: METLIN63158
- ChEMBL: CHEMBL1229250
- MeSH: Guanosine Diphosphate Fucose
- MetaCyc: CPD-13118
- KNApSAcK: C00007245
- foodb: FDB030882
- chemspider: 388350
- CAS: 16597-51-6
- CAS: 15839-70-0
- MoNA: PS024503
- MoNA: PS024501
- MoNA: PS024502
- MoNA: PR100566
- MoNA: PS024506
- MoNA: PS024504
- MoNA: PS024505
- PMhub: MS000010036
- PubChem: 3619
- PDB-CCD: GFB
- 3DMET: B04668
- NIKKAJI: J272.491J
- RefMet: GDP-L-fucose
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
19 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(3)
- GDP-L-fucose biosynthesis II (from L-fucose):
ATP + L-fucose ⟶ β-L-fucose 1-phosphate + ADP - colanic acid building blocks biosynthesis:
α-D-galactose + ATP ⟶ α-D-galactose 1-phosphate + ADP + H+ - GDP-L-fucose biosynthesis I (from GDP-D-mannose):
GDP-L-fucose + NADP+ ⟶ GDP-4-dehydro-6-deoxy-D-mannose + H+ + NADPH
WikiPathways(0)
Plant Reactome(0)
INOH(3)
- Fructose and Mannose metabolism ( Fructose and Mannose metabolism ):
D-Sorbitol + NADP+ ⟶ D-Glucose + NADPH - NADP+ + GDP-L-fucose = NADPH + GDP-4-dehydro-6-deoxy-D-mannose ( Fructose and Mannose metabolism ):
GDP-L-fucose + NADP+ ⟶ GDP-4-dehydro-6-deoxy-D-mannose + NADPH - GTP + L-Fucose 1-phosphate = GDP-L-fucose + Pyrophosphate ( Fructose and Mannose metabolism ):
GDP + L-Fucose 1-phosphate ⟶ GDP-L-fucose + Pyrophosphate
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(13)
- Fructose and Mannose Degradation:
D-Fructose 2,6-bisphosphate + Water ⟶ Fructose 6-phosphate + Phosphate - Fructosuria:
D-Fructose 2,6-bisphosphate + Water ⟶ Fructose 6-phosphate + Phosphate - Fructose Intolerance, Hereditary:
D-Fructose 2,6-bisphosphate + Water ⟶ Fructose 6-phosphate + Phosphate - Mannose Metabolism:
GDP-4-Dehydro-6-deoxy-D-mannose + Hydrogen Ion + NADPH ⟶ GDP-L-fucose + NADP - Colanic Acid Building Blocks Biosynthesis:
-D-Glucose + Phosphocarrier protein HPr ⟶ -D-Glucose 6-phosphate + Phosphocarrier protein HPr - Mannose Metabolism:
ADP-Mannose + Water ⟶ Adenosine monophosphate + D-Mannose 1-phosphate - Fructose and Mannose Degradation:
Fructose 1,6-bisphosphate + Water ⟶ Fructose 6-phosphate + Phosphate - Fructose Intolerance, Hereditary:
Fructose 1,6-bisphosphate + Water ⟶ Fructose 6-phosphate + Phosphate - Fructosuria:
Adenosine triphosphate + D-Fructose ⟶ Adenosine diphosphate + Fructose 6-phosphate - Fructose Intolerance, Hereditary:
Adenosine triphosphate + D-Fructose ⟶ Adenosine diphosphate + Fructose 6-phosphate - Fructose and Mannose Degradation:
Adenosine triphosphate + D-Fructose ⟶ Adenosine diphosphate + Fructose 6-phosphate - Fructose and Mannose Degradation:
Adenosine triphosphate + D-Fructose ⟶ Adenosine diphosphate + Fructose 6-phosphate - Fructosuria:
Fructose 1,6-bisphosphate + Water ⟶ Fructose 6-phosphate + Phosphate
PharmGKB(0)
1 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
- Cezary Waszczak, Dmitry Yarmolinsky, Marina Leal Gavarrón, Triin Vahisalu, Maija Sierla, Olena Zamora, Ross Carter, Tuomas Puukko, Nina Sipari, Airi Lamminmäki, Jörg Durner, Dieter Ernst, J Barbro Winkler, Lars Paulin, Petri Auvinen, Andrew J Fleming, Mats X Andersson, Hannes Kollist, Jaakko Kangasjärvi. Synthesis and import of GDP-l-fucose into the Golgi affect plant-water relations.
The New phytologist.
2023 Nov; ?(?):. doi:
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EMBO molecular medicine.
2021 09; 13(9):e14332. doi:
10.15252/emmm.202114332. [PMID: 34468083] - Li Wan, Yingying Zhu, Wen Li, Wenli Zhang, Wanmeng Mu. Combinatorial Modular Pathway Engineering for Guanosine 5'-Diphosphate-l-fucose Production in Recombinant Escherichia coli.
Journal of agricultural and food chemistry.
2020 May; 68(20):5668-5675. doi:
10.1021/acs.jafc.0c01064. [PMID: 32336091] - Beatriz Gonçalves, Aude Maugarny-Calès, Bernard Adroher, Millán Cortizo, Nero Borrega, Thomas Blein, Alice Hasson, Emilie Gineau, Grégory Mouille, Patrick Laufs, Nicolas Arnaud. GDP-L-fucose is required for boundary definition in plants.
Journal of experimental botany.
2017 12; 68(21-22):5801-5811. doi:
10.1093/jxb/erx402. [PMID: 29186469] - Yiwei Wang, Dan Huang, Kai-Yuan Chen, Min Cui, Weihuan Wang, Xiaoran Huang, Amad Awadellah, Qing Li, Ann Friedman, William W Xin, Luca Di Martino, Fabio Cominelli, Alex Miron, Ricky Chan, James G Fox, Yan Xu, Xiling Shen, Mathew F Kalady, Sanford Markowitz, Ivan Maillard, John B Lowe, Wei Xin, Lan Zhou. Fucosylation Deficiency in Mice Leads to Colitis and Adenocarcinoma.
Gastroenterology.
2017 01; 152(1):193-205.e10. doi:
10.1053/j.gastro.2016.09.004. [PMID: 27639802] - Aline Voxeur, Ludivine Soubigou-Taconnat, Frédéric Legée, Kaori Sakai, Sébastien Antelme, Mylène Durand-Tardif, Catherine Lapierre, Richard Sibout. Altered lignification in mur1-1 a mutant deficient in GDP-L-fucose synthesis with reduced RG-II cross linking.
PloS one.
2017; 12(9):e0184820. doi:
10.1371/journal.pone.0184820. [PMID: 28961242] - Hongchao Wang, Chen Zhang, Haiqin Chen, Qin Yang, Xin Zhou, Zhennan Gu, Hao Zhang, Wei Chen, Yong Q Chen. Biochemical characterization of an isoform of GDP-D-mannose-4,6-dehydratase from Mortierella alpina.
Biotechnology letters.
2016 Oct; 38(10):1761-8. doi:
10.1007/s10529-016-2153-9. [PMID: 27395065] - Joana Rocha, Félix Cicéron, Daniele de Sanctis, Mickael Lelimousin, Valérie Chazalet, Olivier Lerouxel, Christelle Breton. Structure of Arabidopsis thaliana FUT1 Reveals a Variant of the GT-B Class Fold and Provides Insight into Xyloglucan Fucosylation.
The Plant cell.
2016 10; 28(10):2352-2364. doi:
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Biochimie.
2016 Sep; 128-129(?):183-92. doi:
10.1016/j.biochi.2016.08.012. [PMID: 27580247] - Hongchao Wang, Chen Zhang, Haiqin Chen, Qin Yang, Xin Zhou, Zhennan Gu, Hao Zhang, Wei Chen, Yong Q Chen. Characterization of an fungal l-fucokinase involved in Mortierella alpina GDP-l-fucose salvage pathway.
Glycobiology.
2016 08; 26(8):880-887. doi:
10.1093/glycob/cww032. [PMID: 26957583] - Carsten Rautengarten, Berit Ebert, Lifeng Liu, Solomon Stonebloom, Andreia M Smith-Moritz, Markus Pauly, Ariel Orellana, Henrik Vibe Scheller, Joshua L Heazlewood. The Arabidopsis Golgi-localized GDP-L-fucose transporter is required for plant development.
Nature communications.
2016 07; 7(?):12119. doi:
10.1038/ncomms12119. [PMID: 27381418] - Joana Rocha, Félix Cicéron, Olivier Lerouxel, Christelle Breton, Daniele de Sanctis. The galactoside 2-α-L-fucosyltransferase FUT1 from Arabidopsis thaliana: crystallization and experimental MAD phasing.
Acta crystallographica. Section F, Structural biology communications.
2016 07; 72(Pt 7):564-8. doi:
10.1107/s2053230x16009584. [PMID: 27380374] - Jenny C Mortimer, Xiaolan Yu, Sandra Albrecht, Francesca Sicilia, Mariela Huichalaf, Diego Ampuero, Louise V Michaelson, Alex M Murphy, Toshiro Matsunaga, Samantha Kurz, Elaine Stephens, Timothy C Baldwin, Tadashi Ishii, Johnathan A Napier, Andreas P M Weber, Michael G Handford, Paul Dupree. Abnormal glycosphingolipid mannosylation triggers salicylic acid-mediated responses in Arabidopsis.
The Plant cell.
2013 May; 25(5):1881-94. doi:
10.1105/tpc.113.111500. [PMID: 23695979] - Ming Chang, Li-Ping Bai, Jung-Jie Shan, Rong Jiang, Yang Zhang, Lian-Hong Guo, Ren Zhang, Yuan Li. Biochemical characteristics and function of a fucosyltransferase encoded by ste7 in Ebosin biosynthesis of Streptomyces sp. 139.
Journal of microbiology and biotechnology.
2009 Oct; 19(10):1092-7. doi:
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The Journal of biological chemistry.
2008 Jan; 283(1):184-193. doi:
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Glycobiology.
2007 Sep; 17(9):955-62. doi:
10.1093/glycob/cwm066. [PMID: 17602138] - Jaana Niittymäki, Pirkko Mattila, Risto Renkonen. Differential gene expression of GDP-L-fucose-synthesizing enzymes, GDP-fucose transporter and fucosyltransferase VII.
APMIS : acta pathologica, microbiologica, et immunologica Scandinavica.
2006 Jul; 114(7-8):539-48. doi:
10.1111/j.1600-0463.2006.apm_461.x. [PMID: 16907860] - Laura Huopaniemi, Meelis Kolmer, Jaana Niittymäki, Markku Pelto-Huikko, Risto Renkonen. Inflammation-induced transcriptional regulation of Golgi transporters required for the synthesis of sulfo sLex glycan epitopes.
Glycobiology.
2004 Dec; 14(12):1285-94. doi:
10.1093/glycob/cwh131. [PMID: 15269183] - Arjon J van Hengel, Keith Roberts. Fucosylated arabinogalactan-proteins are required for full root cell elongation in arabidopsis.
The Plant journal : for cell and molecular biology.
2002 Oct; 32(1):105-13. doi:
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Science (New York, N.Y.).
2001 Oct; 294(5543):795-7. doi:
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Nature genetics.
2001 May; 28(1):73-6. doi:
10.1038/ng0501-73. [PMID: 11326280] - C P Bonin, W D Reiter. A bifunctional epimerase-reductase acts downstream of the MUR1 gene product and completes the de novo synthesis of GDP-L-fucose in Arabidopsis.
The Plant journal : for cell and molecular biology.
2000 Mar; 21(5):445-54. doi:
10.1046/j.1365-313x.2000.00698.x. [PMID: 10758496] - C Wulff, L Norambuena, A Orellana. GDP-fucose uptake into the Golgi apparatus during xyloglucan biosynthesis requires the activity of a transporter-like protein other than the UDP-glucose transporter.
Plant physiology.
2000 Mar; 122(3):867-77. doi:
10.1104/pp.122.3.867. [PMID: 10712551] - H Leiter, J Mucha, E Staudacher, R Grimm, J Glössl, F Altmann. Purification, cDNA cloning, and expression of GDP-L-Fuc:Asn-linked GlcNAc alpha1,3-fucosyltransferase from mung beans.
The Journal of biological chemistry.
1999 Jul; 274(31):21830-9. doi:
10.1074/jbc.274.31.21830. [PMID: 10419500] - Y Lamrabet, R A Bellogín, T Cubo, R Espuny, A Gil, H B Krishnan, M Megias, F J Ollero, S G Pueppke, J E Ruiz-Sainz, H P Spaink, P Tejero-Mateo, J Thomas-Oates, J M Vinardell. Mutation in GDP-fucose synthesis genes of Sinorhizobium fredii alters Nod factors and significantly decreases competitiveness to nodulate soybeans.
Molecular plant-microbe interactions : MPMI.
1999 Mar; 12(3):207-17. doi:
10.1094/mpmi.1999.12.3.207. [PMID: 10065558] - B J Mengeling, S J Turco. A high-yield, enzymatic synthesis of GDP-D-[3H]arabinose and GDP-L-[3H]fucose.
Analytical biochemistry.
1999 Feb; 267(1):227-33. doi:
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The Journal of biological chemistry.
1998 Nov; 273(46):30165-74. doi:
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Glycobiology.
1998 Feb; 8(2):165-71. doi:
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Proceedings of the National Academy of Sciences of the United States of America.
1997 Mar; 94(5):2085-90. doi:
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Journal of biochemistry.
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The Biochemical journal.
1984 Nov; 224(1):277-84. doi:
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Biochemical and biophysical research communications.
1984 Mar; 119(3):1028-33. doi:
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Clinica chimica acta; international journal of clinical chemistry.
1980 Nov; 108(1):41-8. doi:
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The Biochemical journal.
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Biochimica et biophysica acta.
1979 Jan; 572(1):105-12. doi:
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Journal of the National Cancer Institute.
1978 Jul; 61(1):151-62. doi:
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European journal of biochemistry.
1978 Mar; 84(2):363-8. doi:
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European journal of biochemistry.
1978 Mar; 84(1):161-6. doi:
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Revue francaise de transfusion et immuno-hematologie.
1978 Feb; 21(1):29-46. doi:
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Cancer.
1978 Feb; 41(2):701-5. doi:
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Cancer research.
1978 Jan; 38(1):181-4. doi:
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Cancer treatment reports.
1978 Jan; 62(1):147-9. doi:
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Cancer research.
1977 Aug; 37(8 Pt 1):2557-9. doi:
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Clinical biochemistry.
1977 Aug; 10(4):153-5. doi:
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Journal of the National Cancer Institute.
1977 Jul; 59(1):29-32. doi:
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Biochemical and biophysical research communications.
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