Dolichyl beta-D-mannosyl phosphate (BioDeep_00000027497)

   

human metabolite Endogenous


代谢物信息卡片


{[(6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E,54E,58E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63-hexadecamethyltetrahexaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62-pentadecaen-1-yl]oxy}({[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

化学式: C86H143O9P (1351.0469157999999)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)CCOP(=O)(O)OC1OC(CO)C(O)C(O)C1O
InChI: InChI=1S/C86H143O9P/c1-66(2)33-18-34-67(3)35-19-36-68(4)37-20-38-69(5)39-21-40-70(6)41-22-42-71(7)43-23-44-72(8)45-24-46-73(9)47-25-48-74(10)49-26-50-75(11)51-27-52-76(12)53-28-54-77(13)55-29-56-78(14)57-30-58-79(15)59-31-60-80(16)61-32-62-81(17)63-64-93-96(91,92)95-86-85(90)84(89)83(88)82(65-87)94-86/h33,35,37,39,41,43,45,47,49,51,53,55,57,59,61,81-90H,18-32,34,36,38,40,42,44,46,48,50,52,54,56,58,60,62-65H2,1-17H3,(H,91,92)/b67-35+,68-37+,69-39+,70-41+,71-43+,72-45+,73-47+,74-49+,75-51+,76-53+,77-55+,78-57+,79-59+,80-61+/t81?,82-,83-,84+,85+,86+/m1/s1

描述信息

Dolichyl beta-D-mannosyl phosphate is reversibly produced from dolichyl phosphate and D-mannose, with water as a byproduct. The reaction is catalyzed by the enzyme dolichylphosphate-mannose phosphodiesterase (EC 3.1.4.49). [HMDB]
Dolichyl beta-D-mannosyl phosphate is reversibly produced from dolichyl phosphate and D-mannose, with water as a byproduct. The reaction is catalyzed by the enzyme dolichylphosphate-mannose phosphodiesterase (EC 3.1.4.49).

同义名列表

36 个代谢物同义名

{[(6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E,54E,58E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63-hexadecamethyltetrahexaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62-pentadecaen-1-yl]oxy}({[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid; {[(6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E,54E,58E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63-hexadecamethyltetrahexaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62-pentadecaen-1-yl]oxy}({[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinate; [(6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E,54E,58E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63-hexadecamethyltetrahexaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62-pentadecaen-1-yl]oxy[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphinic acid; beta-D-Mannopyranose-1-ester with dolichol dihydrogen phosphate; b-D-Mannopyranose-1-ester with dolichol dihydrogen phosphate; D-Mannose ester with dolichol dihydrogen phosphate; Alpha-D-Mannopyranosyl phosphate, dolichyl; Phosphate, dolichyl Alpha-D-mannopyranosyl; Dolichyl Alpha-D-mannopyranosyl phosphate; Dolichyl Alpha D mannopyranosyl phosphate; Dolichyl beta-D-mannosyl phosphoric acid; Dolichyl mannosyl mannolipid phosphate; Dolichyl b-D-mannosyl phosphoric acid; Dolichyl β-D-mannosyl phosphoric acid; Phosphate, dolichyl mannopyranosyl; Dolichyl beta-D-mannosyl phosphate; Mannopyranosyl phosphate, dolichyl; Dolichyl mannopyranosyl phosphate; Mannose, dolichol monophosphate; monoPhosphate mannose, dolichol; Dolichyl β-D-mannosyl phosphate; Dolichyl b-D-mannosyl phosphate; Dolichol monophosphate mannose; Phosphoryl dolichol, mannosyl; Dolichyl D-mannosyl phosphate; Dolichol, mannosyl phosphoryl; Dolichyl phosphate D-mannose; Mannosyl phosphate, dolichyl; Mannosyl phosphoryl dolichol; Phosphate, dolichyl mannosyl; Dolichyl mannosyl phosphate; Mannose, dolicholphosphate; Dolicholphosphate mannose; D Mannopyranosyldolichyl; D-Mannopyranosyldolichyl; Mannolipid



数据库引用编号

10 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

25 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(25)

COVID-19 Disease Map(0)

PathBank(0)

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

  • Marianna Zaretsky, Ziqiang Guan, Raz Zarivach, Jerry Eichler. Distinct Regions of the Haloferax volcanii Dolichol Phosphate-Mannose Synthase AglD Mediate the Assembly and Subsequent Processing of the Lipid-Linked Mannose. Journal of bacteriology. 2022 01; 204(1):e0044721. doi: 10.1128/jb.00447-21. [PMID: 34633871]
  • Nurul Jadid, Alexis Samba Mialoundama, Dimitri Heintz, Daniel Ayoub, Mathieu Erhardt, Jérôme Mutterer, Denise Meyer, Abdelmalek Alioua, Alain Van Dorsselaer, Alain Rahier, Bilal Camara, Florence Bouvier. DOLICHOL PHOSPHATE MANNOSE SYNTHASE1 mediates the biogenesis of isoprenyl-linked glycans and influences development, stress response, and ammonium hypersensitivity in Arabidopsis. The Plant cell. 2011 May; 23(5):1985-2005. doi: 10.1105/tpc.111.083634. [PMID: 21558543]
  • Sumana Sanyal, Anant K Menon. Stereoselective transbilayer translocation of mannosyl phosphoryl dolichol by an endoplasmic reticulum flippase. Proceedings of the National Academy of Sciences of the United States of America. 2010 Jun; 107(25):11289-94. doi: 10.1073/pnas.1002408107. [PMID: 20534553]
  • Jeffrey S Rush, Ningguo Gao, Mark A Lehrman, Sergey Matveev, Charles J Waechter. Suppression of Rft1 expression does not impair the transbilayer movement of Man5GlcNAc2-P-P-dolichol in sealed microsomes from yeast. The Journal of biological chemistry. 2009 Jul; 284(30):19835-42. doi: 10.1074/jbc.m109.000893. [PMID: 19494107]
  • Yusuke Maeda, Taroh Kinoshita. Dolichol-phosphate mannose synthase: structure, function and regulation. Biochimica et biophysica acta. 2008 Jun; 1780(6):861-8. doi: 10.1016/j.bbagen.2008.03.005. [PMID: 18387370]
  • Christian G Frank, Markus Aebi. ALG9 mannosyltransferase is involved in two different steps of lipid-linked oligosaccharide biosynthesis. Glycobiology. 2005 Nov; 15(11):1156-63. doi: 10.1093/glycob/cwj002. [PMID: 15987956]
  • Rafael Oriol, Ivan Martinez-Duncker, Isabelle Chantret, Rosella Mollicone, Patrice Codogno. Common origin and evolution of glycosyltransferases using Dol-P-monosaccharides as donor substrate. Molecular biology and evolution. 2002 Sep; 19(9):1451-63. doi: 10.1093/oxfordjournals.molbev.a004208. [PMID: 12200473]
  • M Anand, J S Rush, S Ray, M A Doucey, J Weik, F E Ware, J Hofsteenge, C J Waechter, M A Lehrman. Requirement of the Lec35 gene for all known classes of monosaccharide-P-dolichol-dependent glycosyltransferase reactions in mammals. Molecular biology of the cell. 2001 Feb; 12(2):487-501. doi: 10.1091/mbc.12.2.487. [PMID: 11179430]
  • R Watanabe, Y Murakami, M D Marmor, N Inoue, Y Maeda, J Hino, K Kangawa, M Julius, T Kinoshita. Initial enzyme for glycosylphosphatidylinositol biosynthesis requires PIG-P and is regulated by DPM2. The EMBO journal. 2000 Aug; 19(16):4402-11. doi: 10.1093/emboj/19.16.4402. [PMID: 10944123]
  • D B Moody, T Ulrichs, W Mühlecker, D C Young, S S Gurcha, E Grant, J P Rosat, M B Brenner, C E Costello, G S Besra, S A Porcelli. CD1c-mediated T-cell recognition of isoprenoid glycolipids in Mycobacterium tuberculosis infection. Nature. 2000 Apr; 404(6780):884-8. doi: 10.1038/35009119. [PMID: 10786796]
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  • J C Villagómez-Castro, C Calvo-Méndez, L Vargas-Rodríguez, A Flores-Carreón, E López-Romero. Entamoeba histolytica: solubilization and biochemical characterization of dolichol phosphate mannose synthase, an essential enzyme in glycoprotein biosynthesis. Experimental parasitology. 1998 Feb; 88(2):111-20. doi: 10.1006/expr.1998.4233. [PMID: 9538865]
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  • J S Schutzbach, J W Zimmerman. Yeast dolichyl-phosphomannose synthase: reconstitution of enzyme activity with phospholipids. Biochemistry and cell biology = Biochimie et biologie cellulaire. 1992 Jun; 70(6):460-5. doi: 10.1139/o92-070. [PMID: 1449710]
  • R Cacan, C Villers, M Bélard, A Kaiden, S S Krag, A Verbert. Different fates of the oligosaccharide moieties of lipid intermediates. Glycobiology. 1992 Apr; 2(2):127-36. doi: 10.1093/glycob/2.2.127. [PMID: 1606357]
  • J S Rush, C J Waechter. Expression of dolichol-linked saccharide intermediate synthesis during the development of B lymphocytes. Glycobiology. 1991 Mar; 1(2):229-35. doi: 10.1093/glycob/1.2.229. [PMID: 1726646]
  • N Singh, A M Tartakoff. Two different mutants blocked in synthesis of dolichol-phosphoryl-mannose do not add glycophospholipid anchors to membrane proteins: quantitative correction of the phenotype of a CHO cell mutant with tunicamycin. Molecular and cellular biology. 1991 Jan; 11(1):391-400. doi: 10.1128/mcb.11.1.391-400.1991. [PMID: 1986234]
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  • P J Beck, M J Gething, J Sambrook, M A Lehrman. Complementing mutant alleles define three loci involved in mannosylation of Man5-GlcNAc2-P-P-dolichol in Chinese hamster ovary cells. Somatic cell and molecular genetics. 1990 Nov; 16(6):539-48. doi: 10.1007/bf01233094. [PMID: 2267628]
  • C B Sharma, G P Kaushal, Y T Pan, A D Elbein. Purification and characterization of dolichyl-P-mannose:Man5(GlcNAc)2-PP-dolichol mannosyltransferase. Biochemistry. 1990 Sep; 29(38):8901-7. doi: 10.1021/bi00490a004. [PMID: 2125471]
  • Y T Pan, A D Elbein. Control of N-linked oligosaccharide synthesis: cellular levels of dolichyl phosphate are not the only regulatory factor. Biochemistry. 1990 Sep; 29(35):8077-84. doi: 10.1021/bi00487a013. [PMID: 2148115]
  • A K Menon, R T Schwarz, S Mayor, G A Cross. Cell-free synthesis of glycosyl-phosphatidylinositol precursors for the glycolipid membrane anchor of Trypanosoma brucei variant surface glycoproteins. Structural characterization of putative biosynthetic intermediates. The Journal of biological chemistry. 1990 Jun; 265(16):9033-42. doi: ". [PMID: 1693147]
  • B D Kabakoff, J W Doyle, A A Kandutsch. Relationships among dolichyl phosphate, glycoprotein synthesis, and cell culture growth. Archives of biochemistry and biophysics. 1990 Feb; 276(2):382-9. doi: 10.1016/0003-9861(90)90736-i. [PMID: 2407191]
  • H H Freeze, L Willies, S Hamilton, P Koza-Taylor. Two mutants of Dictyostelium discoideum that lack a sulfated carbohydrate antigenic determinant synthesize a truncated lipid-linked precursor of N-linked oligosaccharides. The Journal of biological chemistry. 1989 Apr; 264(10):5653-9. doi: ". [PMID: 2466828]
  • D K Banerjee. Amphomycin inhibits mannosylphosphoryldolichol synthesis by forming a complex with dolichylmonophosphate. The Journal of biological chemistry. 1989 Feb; 264(4):2024-8. doi: . [PMID: 2464586]
  • A E Chapman, J C Calhoun. Effects of glucose starvation and puromycin treatment on lipid-linked oligosaccharide precursors and biosynthetic enzymes in Chinese hamster ovary cells in vivo and in vitro. Archives of biochemistry and biophysics. 1988 Jan; 260(1):320-33. doi: 10.1016/0003-9861(88)90456-0. [PMID: 3341746]
  • W McDowell, T J Grier, J R Rasmussen, R T Schwarz. The role of C-4-substituted mannose analogues in protein glycosylation. Effect of the guanosine diphosphate esters of 4-deoxy-4-fluoro-D-mannose and 4-deoxy-D-mannose on lipid-linked oligosaccharide assembly. The Biochemical journal. 1987 Dec; 248(2):523-31. doi: 10.1042/bj2480523. [PMID: 2449168]
  • L de la Canal, A J Parodi. Synthesis of dolichol derivatives in trypanosomatids. Characterization of enzymatic patterns. The Journal of biological chemistry. 1987 Aug; 262(23):11128-33. doi: ". [PMID: 3112153]
  • E L Kean, D J DeBrakeleer. Stimulation by dolichol phosphate-mannose of N-acetylglucosaminyl-lipid biosynthesis by membranes from class E Thy-1-negative mutant mouse lymphoma cells which are defective in dolichol phosphate-mannose biosynthesis. Archives of biochemistry and biophysics. 1986 Oct; 250(1):146-52. doi: 10.1016/0003-9861(86)90711-3. [PMID: 3021061]
  • J A Sokoloski, O C Blair, A C Sartorelli. Alterations in glycoprotein synthesis and guanosine triphosphate levels associated with the differentiation of HL-60 leukemia cells produced by inhibitors of inosine 5'-phosphate dehydrogenase. Cancer research. 1986 May; 46(5):2314-9. doi: . [PMID: 2870796]
  • K E Creek, D Rimoldi, A J Clifford, C S Silverman-Jones, L M De Luca. Mannosylation of endogenous and exogenous phosphatidic acid by liver microsomal membranes. Formation of phosphatidylmannose. The Journal of biological chemistry. 1986 Mar; 261(8):3490-500. doi: 10.1016/s0021-9258(17)35675-2. [PMID: 2419333]
  • S V Kyosseva, V I Zhivkov. Biosynthesis of lipid-linked oligosaccharides in embryonic liver. Glucosylation of mannose containing dolichyl diphosphate oligosaccharide. The International journal of biochemistry. 1986; 18(2):195-8. doi: 10.1016/0020-711x(86)90157-6. [PMID: 3949063]
  • K Katamura, T Heike, K Shinomiya, H Mikawa. Regulation of synthesis of N-linked glycoproteins and their lipid intermediates in human T lymphoblastoid cells. The International journal of biochemistry. 1986; 18(11):999-1003. doi: 10.1016/0020-711x(86)90245-4. [PMID: 2433172]
  • T Compton, R J Courtney. Effect of herpes simplex virus type 1 on cellular pools of oligosaccharide-lipid. Virology. 1985 Nov; 147(1):1-8. doi: 10.1016/0042-6822(85)90221-1. [PMID: 2998058]
  • E L Kean. Stimulation by dolichol phosphate-mannose and phospholipids of the biosynthesis of N-acetylglucosaminylpyrophosphoryl dolichol. The Journal of biological chemistry. 1985 Oct; 260(23):12561-71. doi: 10.1016/s0021-9258(17)38908-1. [PMID: 2413026]
  • J Stoll, L Rosenberg, D D Carson, W J Lennarz, S S Krag. A single enzyme catalyzes the synthesis of the mannosylphosphoryl derivative of dolichol and retinol in rat liver and Chinese hamster ovary cells. The Journal of biological chemistry. 1985 Jan; 260(1):232-6. doi: 10.1016/s0021-9258(18)89721-6. [PMID: 4038396]
  • J E Potter. Inflammation-induced increases in dolichol synthesis and hydroxymethylglutaryl-coenzyme A reductase activity in mouse liver are prevented by a high-cholesterol diet but not by fasting. Biochimica et biophysica acta. 1984 Dec; 796(3):393-6. doi: 10.1016/0005-2760(84)90142-5. [PMID: 6509084]
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  • R Tosheva-Tounova, I Krajewska-Rychlik, T Chojnacki. Effect of ethionine on dolichyl phosphate-dependent transglycosylation reactions in rat liver. Acta biochimica Polonica. 1984; 31(1):127-37. doi: ". [PMID: 6720189]
  • Y Shidoji, C S Silverman-Jones, L M De Luca. Retinyl phosphate mannose synthesis in rat liver membranes. Phospholipase sensitivity and phospholipid requirement. The Biochemical journal. 1983 Dec; 216(3):727-35. doi: 10.1042/bj2160727. [PMID: 6199016]
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  • L A Quesada-Allue, A J Parodi. Novel mannose carrier in the trypanosomatid Crithidia fasciculata behaving as a short alpha-saturated polyprenyl phosphate. The Biochemical journal. 1983 Apr; 212(1):123-8. doi: 10.1042/bj2120123. [PMID: 6870847]
  • C L Parfett, J C Jamieson, J A Wright. Changes in cell surface glycoproteins on non-differentiating L6 rat myoblasts selected for resistance to concanavalin A. Experimental cell research. 1983 Apr; 144(2):405-15. doi: 10.1016/0014-4827(83)90420-2. [PMID: 6188627]
  • K E Creek, D J Morré, C S Silverman-Jones, Y Shidoji, L M De Luca. Mannosyl carrier functions of retinyl phosphate and dolichyl phosphate in rat liver endoplasmic reticulum. The Biochemical journal. 1983 Feb; 210(2):541-7. doi: 10.1042/bj2100541. [PMID: 6190478]
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  • L M De Luca, M R Brugh, C S Silverman-Jones, Y Shidoji. Synthesis of retinyl phosphate mannose and dolichyl phosphate mannose from endogenous and exogenous retinyl phosphate and dolichyl phosphate in microsomal fraction. Specific decrease in endogenous retinyl phosphate mannose synthesis in vitamin A deficiency. The Biochemical journal. 1982 Oct; 208(1):159-70. doi: 10.1042/bj2080159. [PMID: 7159390]
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  • J I Rearick, A Chapman, S Kornfeld. Glucose starvation alters lipid-linked oligosaccharide biosynthesis in Chinese hamster ovary cells. The Journal of biological chemistry. 1981 Jun; 256(12):6255-61. doi: NULL. [PMID: 7240203]
  • J I Rearick, K Fujimoto, S Kornfeld. Identification of the mannosyl donors involved in the synthesis of lipid-linked oligosaccharides. The Journal of biological chemistry. 1981 Apr; 256(8):3762-9. doi: ". [PMID: 6163773]
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  • M A Passero, C W Pass, T R Hutchinson. Isolation and identification of a mannolipid intermediate in the synthesis of pulmonary glycoproteins. Experimental lung research. 1981 Mar; 2(1):17-26. doi: 10.3109/01902148109052299. [PMID: 6179772]
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  • P Babczinski. Inhibition of lipid-linked mannose and mannoprotein synthesis in yeast by diumycin in vitro. European journal of biochemistry. 1980 Nov; 112(1):53-8. doi: 10.1111/j.1432-1033.1980.tb04986.x. [PMID: 6161004]
  • B Hoflack, R Cacan, A Verbert. Metabolism of lipid-linked oligosaccharide intermediates in rat spleen lymphocytes. Evidence for ectoglycosyltransferase activities. European journal of biochemistry. 1980 Nov; 112(1):81-6. doi: 10.1111/j.1432-1033.1980.tb04989.x. [PMID: 6161005]
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