Poly-N-acetyllactosamine (BioDeep_00000024095)

   

human metabolite Endogenous


代谢物信息卡片


N-[(2R,3R,4S,5R)-3,5,6-Trihydroxy-1-oxo-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexan-2-yl]ethanimidate

化学式: C14H25NO11 (383.14275399999997)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(=O)NC(C=O)C(C(C(CO)O)OC1C(C(C(C(O1)CO)O)O)O)O
InChI: InChI=1S/C14H25NO11/c1-5(19)15-6(2-16)9(21)13(7(20)3-17)26-14-12(24)11(23)10(22)8(4-18)25-14/h2,6-14,17-18,20-24H,3-4H2,1H3,(H,15,19)

描述信息

Poly-N-acetyllactosamine is a unique carbohydrate composed of N-acetyllactosamine repeats. In particular, poly-N-acetyllactosamine chains are synthesized by repeated alternating additions of N-acetylglucosamine and galactose, catalyzed by -1,3-N-acetylglucosaminyltransferases (poly-N-acetyllactosamine synthase) and -1,4-galactosyltransferases. What is depicted and described in this MetaboCard is a single subunit structure. Poly-N-acetyllactosamine structures occur in mammalian glycoproteins in both N- and O-linked glycans. They represent a backbone for additional modifications by fucosyltransferases, sialyltransferases and sulfotransferases. These glycans have been suggested to be involved in biospecific interactions with selectins and other glycan-binding proteins. Moreover, the poly-Nacetyllactosamine chains in N-glycans have been found to promote tumor progression and metastasis (PMID: 12570780) [HMDB]
Poly-N-acetyllactosamine is a unique carbohydrate composed of N-acetyllactosamine repeats. In particular, poly-N-acetyllactosamine chains are synthesized by repeated alternating additions of N-acetylglucosamine and galactose, catalyzed by -1,3-N-acetylglucosaminyltransferases (poly-N-acetyllactosamine synthase) and -1,4-galactosyltransferases. What is depicted and described in this MetaboCard is a single subunit structure. Poly-N-acetyllactosamine structures occur in mammalian glycoproteins in both N- and O-linked glycans. They represent a backbone for additional modifications by fucosyltransferases, sialyltransferases and sulfotransferases. These glycans have been suggested to be involved in biospecific interactions with selectins and other glycan-binding proteins. Moreover, the poly-Nacetyllactosamine chains in N-glycans have been found to promote tumor progression and metastasis (PMID: 12570780).

同义名列表

11 个代谢物同义名

N-[(2R,3R,4S,5R)-3,5,6-Trihydroxy-1-oxo-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexan-2-yl]ethanimidate; N-[(2R,3R,4S,5R)-3,5,6-trihydroxy-1-oxo-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexan-2-yl]acetamide; 2-(acetylamino)-2-Deoxy-4-O-beta-D-galactopyranosyl-D-glucose homopolymer; 2-(acetylamino)-2-Deoxy-4-O-beta-D-galactopyranosyl-D-glucose; O-beta-D-Galactopyranosyl-(14)-2-deoxy-2-acetamido-D-glucose; N-Acetyl-4-O-beta-D-galactopyranosyl-D-glucosamine; Poly(N-acetyllactosamine); Poly-N-acetyllactosamine; Ammoniumxylenesulfonate; N-Acetyl-lactosamine; PNALA



数据库引用编号

7 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

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。

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文献列表

  • Congcong Chen, Shuaishuai Wang, Madhusudhan Reddy Gadi, He Zhu, Fei Liu, Chang-Cheng Liu, Lei Li, Fengshan Wang, Peixue Ling, Hongzhi Cao. Enzymatic modular synthesis and microarray assay of poly-N-acetyllactosamine derivatives. Chemical communications (Cambridge, England). 2020 Jul; 56(55):7549-7552. doi: 10.1039/d0cc03268a. [PMID: 32579622]
  • Masayuki Nakanishi, Moe Karasudani, Takahiro Shiraishi, Kazunori Hashida, Mami Hino, Michael A J Ferguson, Hiroshi Nomoto. TbGT8 is a bifunctional glycosyltransferase that elaborates N-linked glycans on a protein phosphatase AcP115 and a GPI-anchor modifying glycan in Trypanosoma brucei. Parasitology international. 2014 Jun; 63(3):513-8. doi: 10.1016/j.parint.2014.01.007. [PMID: 24508870]
  • Corwin M Nycholat, Wenjie Peng, Ryan McBride, Aristotelis Antonopoulos, Robert P de Vries, Zinaida Polonskaya, M G Finn, Anne Dell, Stuart M Haslam, James C Paulson. Synthesis of biologically active N- and O-linked glycans with multisialylated poly-N-acetyllactosamine extensions using P. damsela α2-6 sialyltransferase. Journal of the American Chemical Society. 2013 Dec; 135(49):18280-18283. doi: 10.1021/ja409781c. [PMID: 24256304]
  • Rebecca P Hughey. The sweet side of urea transporters. American journal of physiology. Renal physiology. 2012 Aug; 303(3):F375-6. doi: 10.1152/ajprenal.00250.2012. [PMID: 22573383]
  • Hua Su, Conner B Carter, Otto Fröhlich, Richard D Cummings, Guangping Chen. Glycoforms of UT-A3 urea transporter with poly-N-acetyllactosamine glycosylation have enhanced transport activity. American journal of physiology. Renal physiology. 2012 Jul; 303(2):F201-8. doi: 10.1152/ajprenal.00140.2012. [PMID: 22535801]
  • J Stoyloff, S Ivanov. Isolation and characterization of galactose-specific carbohydrate-binding protein from Guerin tumor cells. Brain research bulletin. 2010 Aug; 83(1-2):65-75. doi: 10.1016/j.brainresbull.2010.06.008. [PMID: 20599595]
  • Abdelmadjid Atrih, Julia M Richardson, Alan R Prescott, Michael A J Ferguson. Trypanosoma brucei glycoproteins contain novel giant poly-N-acetyllactosamine carbohydrate chains. The Journal of biological chemistry. 2005 Jan; 280(2):865-71. doi: 10.1074/jbc.m411061200. [PMID: 15509560]
  • Sean R Stowell, Marcelo Dias-Baruffi, Leena Penttilä, Ossi Renkonen, A Kwame Nyame, Richard D Cummings. Human galectin-1 recognition of poly-N-acetyllactosamine and chimeric polysaccharides. Glycobiology. 2004 Feb; 14(2):157-67. doi: 10.1093/glycob/cwh018. [PMID: 14576172]
  • M Beppu, K Ando, M Saeki, N Yokoyama, K Kikugawa. Binding of oxidized Jurkat cells to THP-1 macrophages and antiband 3 IgG through sialylated poly-N-acetyllactosaminyl sugar chains. Archives of biochemistry and biophysics. 2000 Dec; 384(2):368-74. doi: 10.1006/abbi.2000.2122. [PMID: 11368325]
  • G Y Chen, N Kurosawa, T Muramatsu. A novel variant form of murine beta-1, 6-N-acetylglucosaminyltransferase forming branches in poly-N-acetyllactosamines. Glycobiology. 2000 Oct; 10(10):1001-11. doi: 10.1093/glycob/10.10.1001. [PMID: 11030746]
  • D P Nolan, M Geuskens, E Pays. N-linked glycans containing linear poly-N-acetyllactosamine as sorting signals in endocytosis in Trypanosoma brucei. Current biology : CB. 1999 Oct; 9(20):1169-72. doi: 10.1016/s0960-9822(00)80018-4. [PMID: 10531030]
  • S Di Virgilio, J Glushka, K Moremen, M Pierce. Enzymatic synthesis of natural and 13C enriched linear poly-N-acetyllactosamines as ligands for galectin-1. Glycobiology. 1999 Apr; 9(4):353-64. doi: 10.1093/glycob/9.4.353. [PMID: 10089209]
  • K Sasaki, K Kurata-Miura, M Ujita, K Angata, S Nakagawa, S Sekine, T Nishi, M Fukuda. Expression cloning of cDNA encoding a human beta-1,3-N-acetylglucosaminyltransferase that is essential for poly-N-acetyllactosamine synthesis. Proceedings of the National Academy of Sciences of the United States of America. 1997 Dec; 94(26):14294-9. doi: 10.1073/pnas.94.26.14294. [PMID: 9405606]
  • R S Bresalier, J C Byrd, L Wang, A Raz. Colon cancer mucin: a new ligand for the beta-galactoside-binding protein galectin-3. Cancer research. 1996 Oct; 56(19):4354-7. doi: NULL. [PMID: 8813123]
  • J Müthing. Influenza A and Sendai viruses preferentially bind to fucosylated gangliosides with linear poly-N-acetyllactosaminyl chains from human granulocytes. Carbohydrate research. 1996 Sep; 290(2):217-24. doi: 10.1016/0008-6215(96)00149-8. [PMID: 8823909]
  • N Ito, S Imai, S Haga, C Nagaike, Y Morimura, K Hatake. Localization of binding sites of Ulex europaeus I, Helix pomatia and Griffonia simplicifolia I-B4 lectins and analysis of their backbone structures by several glycosidases and poly-N-acetyllactosamine-specific lectins in human breast carcinomas. Histochemistry and cell biology. 1996 Sep; 106(3):331-9. doi: . [PMID: 8897074]
  • K Ando, K Kikugawa, M Beppu. Binding of anti-band 3 autoantibody to sialylated poly-N-acetyllactosaminyl sugar chains of band 3 glycoprotein on polyvinylidene difluoride membrane and sepharose gel: further evidence for anti-band 3 autoantibody binding to the sugar chains of oxidized and senescent erythrocytes. Journal of biochemistry. 1996 Apr; 119(4):639-47. doi: 10.1093/oxfordjournals.jbchem.a021290. [PMID: 8743563]
  • J Müthing, R Spanbroek, J Peter-Katalinić, F G Hanisch, C Hanski, A Hasegawa, F Unland, J Lehmann, H Tschesche, H Egge. Isolation and structural characterization of fucosylated gangliosides with linear poly-N-acetyllactosaminyl chains from human granulocytes. Glycobiology. 1996 Mar; 6(2):147-56. doi: 10.1093/glycob/6.2.147. [PMID: 8727787]
  • M Beppu, S Eda, M Fujimaki, E Hishiyama, K Kikugawa. Recognition of poly-N-acetyllactosaminyl saccharide chains on iron-oxidized erythrocytes by human monocytic leukemia cell line THP-1 differentiated into macrophages. Biological & pharmaceutical bulletin. 1996 Feb; 19(2):188-94. doi: 10.1248/bpb.19.188. [PMID: 8850303]
  • A Velasco, E Caminos, E Vecino, J M Lara, J Aijón. Microglia in normal and regenerating visual pathways of the tench (Tinca tinca L., 1758; Teleost): a study with tomato lectin. Brain research. 1995 Dec; 705(1-2):315-24. doi: 10.1016/0006-8993(95)01204-4. [PMID: 8821763]
  • Y Konami, T Uno, M Fujii, K Yamamoto, T Osawa, T Irimura. A high degree of sequence homology in the putative carbohydrate recognition domains of pokeweed mitogen and wheat germ agglutinin: poly-N-acetyllactosamine-binding lectins from different species. Glycobiology. 1995 Oct; 5(7):663-70. doi: 10.1093/glycob/5.7.663. [PMID: 8608268]
  • L Acarin, J M Vela, B González, B Castellano. Demonstration of poly-N-acetyl lactosamine residues in ameboid and ramified microglial cells in rat brain by tomato lectin binding. The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society. 1994 Aug; 42(8):1033-41. doi: 10.1177/42.8.8027523. [PMID: 8027523]
  • N Ito, S Kawahara, Y Hirano, Y Morimura, K Nakajima, K Uchida, T Hirota. Localization of blood-group-related linear poly-N-acetyllactosamine structure in different human tissues by Griffonia simplicifolia agglutinin-II staining following endo-beta-galactosidase digestion. The Histochemical journal. 1994 Apr; 26(4):327-36. doi: 10.1007/bf00157766. [PMID: 8040005]
  • G Uhlenbruck, F G Hanisch, Z Kljajic, S Poznanovic, H C Schröder, W E Müller. The lectin from the algae Udotea petiolata: isolation, characterization and sugar binding properties. Behring Institute Mitteilungen. 1992 Apr; ?(91):67-77. doi: NULL. [PMID: 1524573]
  • J M Callaghan, B H Toh, J M Pettitt, D C Humphris, P A Gleeson. Poly-N-acetyllactosamine-specific tomato lectin interacts with gastric parietal cells. Identification of a tomato-lectin binding 60-90 X 10(3) Mr membrane glycoprotein of tubulovesicles. Journal of cell science. 1990 Apr; 95 ( Pt 4)(?):563-76. doi: 10.1242/jcs.95.4.563. [PMID: 2166741]
  • D Spillmann, J Finne. Poly-N-acetyllactosamine glycans of cellular glycoproteins: predominance of linear chains in mouse neuroblastoma and rat pheochromocytoma cell lines. Journal of neurochemistry. 1987 Sep; 49(3):874-83. doi: 10.1111/j.1471-4159.1987.tb00975.x. [PMID: 3302106]
  • R K Merkle, R D Cummings. Relationship of the terminal sequences to the length of poly-N-acetyllactosamine chains in asparagine-linked oligosaccharides from the mouse lymphoma cell line BW5147. Immobilized tomato lectin interacts with high affinity with glycopeptides containing long poly-N-acetyllactosamine chains. The Journal of biological chemistry. 1987 Jun; 262(17):8179-89. doi: ". [PMID: 3597368]
  • M N Fukuda, B Bothner, P Scartezzini, A Dell. Isolation and characterization of poly-N-acetyllactosaminylceramides accumulated in the erythrocytes of congenital dyserythropoietic anemia type II patients. Chemistry and physics of lipids. 1986 Dec; 42(1-3):185-97. doi: 10.1016/0009-3084(86)90052-6. [PMID: 3829205]
  • S Nomoto, H Muramatsu, M Ozawa, T Suganuma, M Tashiro, T Muramatsu. An anti-carbohydrate monoclonal antibody inhibits cell-substratum adhesion of F9 embryonal carcinoma cells. Experimental cell research. 1986 May; 164(1):49-62. doi: 10.1016/0014-4827(86)90453-2. [PMID: 3754220]