N-acetyllactosamine (BioDeep_00000405453)

Main id: BioDeep_00000001388

 

PANOMIX_OTCML-2023


代谢物信息卡片


N-Acetyl-D-lactosamine

化学式: C14H25NO11 (383.14275399999997)
中文名称: N -乙酰- D- 乳糖胺
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(=O)NC1C(C(C(OC1O)CO)OC2C(C(C(C(O2)CO)O)O)O)O
InChI: InChI=1S/C14H25NO11/c1-4(18)15-7-9(20)12(6(3-17)24-13(7)23)26-14-11(22)10(21)8(19)5(2-16)25-14/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8+,9-,10+,11-,12-,13-,14+/m1/s1

描述信息

A beta-D-galactopyranosyl-(1->4)-N-acetyl-D-glucosamine having beta-configuration at the reducing end anomeric centre.
N-Acetyllactosamine (LacNAc), a nitrogen-containing disaccharide, is an important component of various oligosaccharides such as glycoproteins and sialyl Lewis X. N-Acetyllactosamine can be used as the starting material for the synthesis of various oligosaccharides. N-Acetyllactosamine has prebiotic effects[1][2].

同义名列表

2 个代谢物同义名

N-Acetyl-D-lactosamine; N-acetyllactosamine



数据库引用编号

13 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

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)

0 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

  • Zhen Sun, Lili Zhang, Lihua Li, Chen Shao, Jia Liu, Mengxue Zhou, Zhongqun Wang. Galectin-3 mediates cardiac remodeling caused by impaired glucose and lipid metabolism through inhibiting two pathways of activating Akt. American journal of physiology. Heart and circulatory physiology. 2021 01; 320(1):H364-H380. doi: 10.1152/ajpheart.00523.2020. [PMID: 33275526]
  • Jing Han, Yiqing Pan, Yong Gu, Xiaoyan Xu, Ran Zhao, Jichen Sha, Rongrong Zhang, Jianxin Gu, Shifang Ren. Profiling of IgG N-glycome during mouse aging: Fucosylated diantennary glycans containing one Neu5Gc-linked LacNAc are associated with age. Journal of proteomics. 2020 10; 229(?):103966. doi: 10.1016/j.jprot.2020.103966. [PMID: 32891889]
  • Ben Cowper, Martin Lavén, Birgit Hakkarainen, Ezra Mulugeta. Glycan analysis of erythropoiesis-stimulating agents. Journal of pharmaceutical and biomedical analysis. 2020 Feb; 180(?):113031. doi: 10.1016/j.jpba.2019.113031. [PMID: 31838284]
  • Dominic Laaf, Pavla Bojarová, Helena Pelantová, Vladimír Křen, Lothar Elling. Tailored Multivalent Neo-Glycoproteins: Synthesis, Evaluation, and Application of a Library of Galectin-3-Binding Glycan Ligands. Bioconjugate chemistry. 2017 11; 28(11):2832-2840. doi: 10.1021/acs.bioconjchem.7b00520. [PMID: 28976746]
  • Hui Luo, Bin Liu, Lin Zhao, Jingni He, Tangzhiming Li, Lihuang Zha, Xiaohui Li, Qiangqiang Qi, Yuwei Liu, Zaixin Yu. Galectin-3 mediates pulmonary vascular remodeling in hypoxia-induced pulmonary arterial hypertension. Journal of the American Society of Hypertension : JASH. 2017 Oct; 11(10):673-683.e3. doi: 10.1016/j.jash.2017.07.009. [PMID: 28826890]
  • Thomas Fischöder, Dominic Laaf, Carina Dey, Lothar Elling. Enzymatic Synthesis of N-Acetyllactosamine (LacNAc) Type 1 Oligomers and Characterization as Multivalent Galectin Ligands. Molecules (Basel, Switzerland). 2017 Aug; 22(8):. doi: 10.3390/molecules22081320. [PMID: 28796164]
  • Anne-Roos S Frenay, Lili Yu, A Rogier van der Velde, Inge Vreeswijk-Baudoin, Natalia López-Andrés, Harry van Goor, Herman H Silljé, Willem P Ruifrok, Rudolf A de Boer. Pharmacological inhibition of galectin-3 protects against hypertensive nephropathy. American journal of physiology. Renal physiology. 2015 Mar; 308(5):F500-9. doi: 10.1152/ajprenal.00461.2014. [PMID: 25503732]
  • E Silva, G Kadirvel, R Jiang, N Bovin, D Miller. Multiple proteins from ejaculated and epididymal porcine spermatozoa bind glycan motifs found in the oviduct. Andrology. 2014 Sep; 2(5):763-71. doi: 10.1111/j.2047-2927.2014.00249.x. [PMID: 25079898]
  • Kosuke Nakamura, Hiromi Sakagami, Kimie Asanuma-Date, Nao Nagasawa, Yoshiaki Nakahara, Hiroshi Akiyama, Haruko Ogawa. Immobilized glycosylated Fmoc-amino acid for SPR: comparative studies of lectin-binding to linear or biantennary diLacNAc structures. Carbohydrate research. 2013 Dec; 382(?):77-85. doi: 10.1016/j.carres.2013.10.003. [PMID: 24211369]
  • Shui-Hua Wang, Chih-Ming Tsai, Kuo-I Lin, Kay-Hooi Khoo. Advanced mass spectrometry and chemical analyses reveal the presence of terminal disialyl motif on mouse B-cell glycoproteins. Glycobiology. 2013 Jun; 23(6):677-89. doi: 10.1093/glycob/cwt008. [PMID: 23363740]
  • C Hamsten, M Starkhammar, T A T Tran, M Johansson, U Bengtsson, G Ahlén, M Sällberg, H Grönlund, M van Hage. Identification of galactose-α-1,3-galactose in the gastrointestinal tract of the tick Ixodes ricinus; possible relationship with red meat allergy. Allergy. 2013 Apr; 68(4):549-52. doi: 10.1111/all.12128. [PMID: 23414348]
  • Etsuko Mori, Hiroyuki Fukuda, Shinobu Imajoh-Ohmi, Tsuneatsu Mori, Seiichi Takasaki. Purification of N-acetyllactosamine-binding activity from the porcine sperm membrane: possible involvement of an ADAM complex in the carbohydrate-binding activity of sperm. The Journal of reproduction and development. 2012; 58(1):117-25. doi: 10.1262/jrd.11-108n. [PMID: 22052010]
  • Patrick R Romano, Andrew Mackay, Minh Vong, Johann DeSa, Anne Lamontagne, Mary Ann Comunale, Julie Hafner, Timothy Block, Ryszard Lec, Anand Mehta. Development of recombinant Aleuria aurantia lectins with altered binding specificities to fucosylated glycans. Biochemical and biophysical research communications. 2011 Oct; 414(1):84-9. doi: 10.1016/j.bbrc.2011.09.027. [PMID: 21945439]
  • Chih-Ming Tsai, Chin-Huey Guan, Hsiao-Wu Hsieh, Tsui-Ling Hsu, Zhijay Tu, Kuan-Jung Wu, Chun-Hung Lin, Kuo-I Lin. Galectin-1 and galectin-8 have redundant roles in promoting plasma cell formation. Journal of immunology (Baltimore, Md. : 1950). 2011 Aug; 187(4):1643-52. doi: 10.4049/jimmunol.1100297. [PMID: 21753146]
  • Sabine André, Cyrille Grandjean, François-Moana Gautier, Silvia Bernardi, Francesco Sansone, Hans-Joachim Gabius, Rocco Ungaro. Combining carbohydrate substitutions at bioinspired positions with multivalent presentation towards optimising lectin inhibitors: case study with calixarenes. Chemical communications (Cambridge, England). 2011 Jun; 47(21):6126-8. doi: 10.1039/c1cc11163a. [PMID: 21523264]
  • Ryo Matsumoto, Tomoko F Shibata, Hisanori Kohtsuka, Mamoru Sekifuji, Natsuko Sugii, Hiroaki Nakajima, Noriaki Kojima, Yuki Fujii, Sarkar M A Kawsar, Hidetaro Yasumitsu, Jiharu Hamako, Taei Matsui, Yasuhiro Ozeki. Glycomics of a novel type-2 N-acetyllactosamine-specific lectin purified from the feather star, Oxycomanthus japonicus (Pelmatozoa: Crinoidea). Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology. 2011 Apr; 158(4):266-73. doi: 10.1016/j.cbpb.2010.12.004. [PMID: 21176791]
  • Ravi S Loka, Christopher M Sadek, Nikolas A Romaniuk, Christopher W Cairo. Conjugation of synthetic N-acetyl-lactosamine to azide-containing proteins using the Staudinger ligation. Bioconjugate chemistry. 2010 Oct; 21(10):1842-9. doi: 10.1021/bc100209r. [PMID: 20845977]
  • Weiduan Xu, Jianmin Chen, Glenn Yamasaki, John E Murphy, Baisong Mei. Lectin binding assays for in-process monitoring of sialylation in protein production. Molecular biotechnology. 2010 Jul; 45(3):248-56. doi: 10.1007/s12033-010-9272-7. [PMID: 20379804]
  • Ryuichi Masaka, Makoto Ogata, Yoshinori Misawa, Megumi Yano, Chika Hashimoto, Takeomi Murata, Hirokazu Kawagishi, Taichi Usui. Molecular design of N-linked tetravalent glycosides bearing N-acetylglucosamine, N,N'-diacetylchitobiose and N-acetyllactosamine: Analysis of cross-linking activities with WGA and ECA lectins. Bioorganic & medicinal chemistry. 2010 Jan; 18(2):621-9. doi: 10.1016/j.bmc.2009.12.006. [PMID: 20056550]
  • Nicole Koropatkin, Eric C Martens, Jeffrey I Gordon, Thomas J Smith. Structure of a SusD homologue, BT1043, involved in mucin O-glycan utilization in a prominent human gut symbiont. Biochemistry. 2009 Feb; 48(7):1532-42. doi: 10.1021/bi801942a. [PMID: 19191477]
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  • Hiroko Matsushita-Oikawa, Mayumi Komatsu, Naoko Iida-Tanaka, Hiromi Sakagami, Tetsuko Kanamori, Isamu Matsumoto, Nobuko Seno, Haruko Ogawa. Novel carbohydrate-binding activity of bovine liver beta-glucuronidase toward lactose/N-acetyllactosamine sequences. Glycobiology. 2006 Oct; 16(10):891-901. doi: 10.1093/glycob/cwl016. [PMID: 16774908]
  • Romney M Hyland, Thomas P Griener, George L Mulvey, Pavel I Kitov, Om P Srivastava, Paola Marcato, Glen D Armstrong. Basis for N-acetyllactosamine-mediated inhibition of enteropathogenic Escherichia coli localized adherence. Journal of medical microbiology. 2006 Jun; 55(Pt 6):669-675. doi: 10.1099/jmm.0.46344-0. [PMID: 16687583]
  • Shoudou Kojima, Hironobu Eguchi, Tomomi Ookawara, Noriko Fujiwara, Jun Yasuda, Kazuhiko Nakagawa, Takehira Yamamura, Keiichiro Suzuki. Clostridium botulinum type A progenitor toxin binds to Intestine-407 cells via N-acetyllactosamine moiety. Biochemical and biophysical research communications. 2005 Jun; 331(2):571-6. doi: 10.1016/j.bbrc.2005.04.007. [PMID: 15850798]
  • Olivier Manches, Joel Plumas, Gabrielle Lui, Laurence Chaperot, Jean-Paul Molens, Jean-Jacques Sotto, Jean-Claude Bensa, Uri Galili. Anti-Gal-mediated targeting of human B lymphoma cells to antigen-presenting cells: a potential method for immunotherapy using autologous tumor cells. Haematologica. 2005 May; 90(5):625-34. doi: NULL. [PMID: 15921377]
  • Marian C Bryan, Lac V Lee, Chi-Huey Wong. High-throughput identification of fucosyltransferase inhibitors using carbohydrate microarrays. Bioorganic & medicinal chemistry letters. 2004 Jun; 14(12):3185-8. doi: 10.1016/j.bmcl.2004.04.001. [PMID: 15149672]
  • Rayapati A Naidu, Caroline J Ingle, Carl M Deom, John L Sherwood. The two envelope membrane glycoproteins of Tomato spotted wilt virus show differences in lectin-binding properties and sensitivities to glycosidases. Virology. 2004 Feb; 319(1):107-17. doi: 10.1016/j.virol.2003.10.012. [PMID: 14967492]
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  • A Suzuki, N Hiraoka, M Suzuki, K Angata, A K Misra, J McAuliffe, O Hindsgaul, M Fukuda. Molecular cloning and expression of a novel human beta-Gal-3-O-sulfotransferase that acts preferentially on N-acetyllactosamine in N- and O-glycans. The Journal of biological chemistry. 2001 Jun; 276(26):24388-95. doi: 10.1074/jbc.m103135200. [PMID: 11323440]
  • B K Chacko, P S Appukuttan. Peanut (Arachis hypogaea) lectin recognizes alpha-linked galactose, but not N-acetyl lactosamine in N-linked oligosaccharide terminals. International journal of biological macromolecules. 2001 Jun; 28(5):365-71. doi: 10.1016/s0141-8130(01)00139-8. [PMID: 11325423]
  • N Yoshitani, E Mori, S Takasaki. Detection of carbohydrate recognition molecules on the plasma membrane of boar sperm by dextran-based multivalent oligosaccharide probes. Glycobiology. 2001 Apr; 11(4):313-20. doi: 10.1093/glycob/11.4.313. [PMID: 11358880]
  • J Ciopraga, J Angström, J Bergström, T Larsson, N Karlsson, C Motas, O Gozia, S Teneberg. Isolectins from Solanum tuberosum with different detailed carbohydrate binding specificities: unexpected recognition of lactosylceramide by N-acetyllactosamine-binding lectins. Journal of biochemistry. 2000 Nov; 128(5):855-67. doi: 10.1093/oxfordjournals.jbchem.a022824. [PMID: 11056399]
  • S Teneberg, A Berntsson, J Angström. Common architecture of the primary galactose binding sites of Erythrina corallodendron lectin and heat-labile enterotoxin from Escherichia coli in relation to the binding of branched neolactohexaosylceramide. Journal of biochemistry. 2000 Sep; 128(3):481-91. doi: 10.1093/oxfordjournals.jbchem.a022778. [PMID: 10965049]
  • K Ando, T Hagiwara, M Beppu, K Kikugawa. Naturally occurring anti-band 3 antibody binds to apoptotic human T-lymphoid cell line Jurkat through sialylated poly-N-acetyllactosaminyl saccharide chains on the cell surface. Biochemical and biophysical research communications. 2000 Aug; 275(2):412-7. doi: 10.1006/bbrc.2000.3322. [PMID: 10964679]
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  • N Parkhomovskiy, A Kammesheidt, P T Martin. N-acetyllactosamine and the CT carbohydrate antigen mediate agrin-dependent activation of MuSK and acetylcholine receptor clustering in skeletal muscle. Molecular and cellular neurosciences. 2000 Apr; 15(4):380-97. doi: 10.1006/mcne.2000.0835. [PMID: 10845774]
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  • J J van Rooijen, J P Kamerling, J F Vliegenthart. The abundance of additional N-acetyllactosamine units in N-linked tetraantennary oligosaccharides of human Tamm-Horsfall glycoprotein is a donor-specific feature. Glycobiology. 1998 Nov; 8(11):1065-75. doi: 10.1093/glycob/8.11.1065. [PMID: 9751793]
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