N-Acetyllactosamine (BioDeep_00000001388)

 

Secondary id: BioDeep_00000405453, BioDeep_00000897520

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


N-[(2R,3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide

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 Homo sapiens(blood) 2.78%

分子结构信息

SMILES: CC(=O)NC(C=O)C(O)C(OC1OC(CO)C(O)C(O)C1O)C(O)CO.CC(=O)NC1C(O)OC(CO)C(OC2OC(CO)C(O)C(O)C2O)C1O
InChI: 2,6-14,17-18,20-24H,3-4H2,1H3,(H,15,19)

描述信息

N-Acetyllactosamine, also known as galb1-4glcnacb or lacnac, belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. N-Acetyllactosamine exists in all living organisms, ranging from bacteria to humans.
Structural unit in higher oligosaccharides present in human milk
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

21 个代谢物同义名

N-[(2R,3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide; beta-delta-Galactosyl-1,4-N-acetyl-beta-delta-glucosamine; beta-delta-Galactosyl-1,4-N-acetyl-delta-glucosamine; beta-D-Galactosyl-1,4-N-acetyl-beta-D-glucosamine; beta-D-Galactosyl-1,4-N-acetyl-D-glucosamine; b-D-Galactosyl-1,4-N-acetyl-b-D-glucosamine; Β-D-galactosyl-1,4-N-acetyl-β-D-glucosamine; Β-D-galactosyl-1,4-N-acetyl-D-glucosamine; b-D-Galactosyl-1,4-N-acetyl-D-glucosamine; N-Acetyl-beta-lactosamine; N-Acetyl-D-lactosamine; N-Acetyl-β-lactosamine; delta-Galactopyranosyl; N-Acetyl-b-lactosamine; Galbeta1-4glcnacbeta; N-Acetyl-lactosamine; N-acetyllactosamine; ACETYL lactosamine; D-Galactopyranosyl; Galb1-4glcnacb; LacNAc



数据库引用编号

16 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)

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

  • 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]
  • Joanne L Zahorsky-Reeves, Mary K Kearns-Jonker, Tuan T Lam, Jeremy R Jackson, Randall E Morris, Vaughn A Starnes, Donald V Cramer. The xenoantibody response and immunoglobulin gene expression profile of cynomolgus monkeys transplanted with hDAF-transgenic porcine hearts. Xenotransplantation. 2007 Mar; 14(2):135-44. doi: 10.1111/j.1399-3089.2007.00381.x. [PMID: 17381688]
  • Alice L Erwin, Simon Allen, Derek K Ho, Paul J Bonthuis, Paul J Bonthius, Justin Jarisch, Kevin L Nelson, David L Tsao, William C T Unrath, Michael E Watson, Bradford W Gibson, Michael A Apicella, Arnold L Smith. Role of lgtC in resistance of nontypeable Haemophilus influenzae strain R2866 to human serum. Infection and immunity. 2006 Nov; 74(11):6226-35. doi: 10.1128/iai.00722-06. [PMID: 16966407]
  • 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]
  • P S Appukuttan. Terminal alpha-linked galactose rather than N-acetyl lactosamine is ligand for bovine heart galectin-1 in N-linked oligosaccharides of glycoproteins. Journal of molecular recognition : JMR. 2002 Jul; 15(4):180-7. doi: 10.1002/jmr.573. [PMID: 12382235]
  • 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]
  • G M Bradbrook, J R Forshaw, S Pérez. Structure/thermodynamics relationships of lectin-saccharide complexes: the Erythrina corallodendron case. European journal of biochemistry. 2000 Jul; 267(14):4545-55. doi: 10.1046/j.1432-1327.2000.01505.x. [PMID: 10880979]
  • 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]
  • N Hasegawa, T Torii, I Nagaoka, K Nakayasu, H Miyajima, O Habuchi. Measurement of activities of human serum sulfotransferases which transfer sulfate to the galactose residues of keratan sulfate and to the nonreducing end N-acetylglucosamine residues of N-acetyllactosamine trisaccharide: comparison between normal controls and patients with macular corneal dystrophy. Journal of biochemistry. 1999 Feb; 125(2):245-52. doi: 10.1093/oxfordjournals.jbchem.a022280. [PMID: 9990120]
  • 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]
  • X Zeng, T Murata, H Kawagishi, T Usui, K Kobayashi. Analysis of specific interactions of synthetic glycopolypeptides carrying N-acetyllactosamine and related compounds with lectins. Carbohydrate research. 1998 Nov; 312(4):209-17. doi: 10.1016/s0008-6215(98)00259-6. [PMID: 9861697]
  • S Elgavish, B Shaanan. Structures of the Erythrina corallodendron lectin and of its complexes with mono- and disaccharides. Journal of molecular biology. 1998 Apr; 277(4):917-32. doi: 10.1006/jmbi.1998.1664. [PMID: 9545381]
  • Y Shinohara, Y Hasegawa, H Kaku, N Shibuya. Elucidation of the mechanism enhancing the avidity of lectin with oligosaccharides on the solid phase surface. Glycobiology. 1997 Dec; 7(8):1201-8. doi: 10.1093/glycob/7.8.1201. [PMID: 9455921]
  • D Zanini, R Roy. Chemoenzymatic synthesis and lectin binding properties of dendritic N-acetyllactosamine. Bioconjugate chemistry. 1997 Mar; 8(2):187-92. doi: 10.1021/bc970005u. [PMID: 9095359]
  • R Adar, N Sharon. Mutational studies of the amino acid residues in the combining site of Erythrina corallodendron lectin. European journal of biochemistry. 1996 Aug; 239(3):668-74. doi: 10.1111/j.1432-1033.1996.0668u.x. [PMID: 8774711]
  • J H Wu, W M Watkins, C P Chen, S C Song, A M Wu. Interaction of a human blood group Sd(a-) Tamm-Horsfall glycoprotein with applied lectins. FEBS letters. 1996 Apr; 384(3):231-4. doi: 10.1016/0014-5793(96)00320-1. [PMID: 8617360]
  • R Mollicone, A Cailleau, A Imberty, P Gane, S Perez, R Oriol. Recognition of the blood group H type 2 trisaccharide epitope by 28 monoclonal antibodies and three lectins. Glycoconjugate journal. 1996 Apr; 13(2):263-71. doi: 10.1007/bf00731501. [PMID: 8737251]
  • K Kasai, J Hirabayashi. Galectins: a family of animal lectins that decipher glycocodes. Journal of biochemistry. 1996 Jan; 119(1):1-8. doi: 10.1093/oxfordjournals.jbchem.a021192. [PMID: 8907168]
  • P Bastiani, M J Papandreou, O Blanck, E Fenouillet, V Thibault, R Miquelis. On the relationship between completion of N-acetyllactosamine oligosaccharide units and iodine content of thyroglobulin: a reinvestigation. Endocrinology. 1995 Oct; 136(10):4204-9. doi: 10.1210/endo.136.10.7664637. [PMID: 7664637]
  • A K Allen. Purification and characterization of an N-acetyllactosamine-specific lectin from tubers of Arum maculatum. Biochimica et biophysica acta. 1995 May; 1244(1):129-32. doi: 10.1016/0304-4165(94)00210-o. [PMID: 7766648]
  • N Le Marer, D Stéhelin. High alpha-2,6-sialylation of N-acetyllactosamine sequences in ras-transformed rat fibroblasts correlates with high invasive potential. Glycobiology. 1995 Mar; 5(2):219-26. doi: 10.1093/glycob/5.2.219. [PMID: 7780196]
  • D Ivanov, V Karaivanova, S Ivanov, H Chelibonova-Lorer. Comparative studies on the uridine-5'-diphosphate-galactose: glycoprotein galactosyltransferase activity in rat liver and Zajdela ascitic hepatoma. Cancer biochemistry biophysics. 1994 Apr; 14(1):35-40. doi: NULL. [PMID: 7540947]
  • D I Liao, G Kapadia, H Ahmed, G R Vasta, O Herzberg. Structure of S-lectin, a developmentally regulated vertebrate beta-galactoside-binding protein. Proceedings of the National Academy of Sciences of the United States of America. 1994 Feb; 91(4):1428-32. doi: 10.1073/pnas.91.4.1428. [PMID: 8108426]
  • S Onodera. A microplate assay for sialidase activity using plant lectin binding to N-acetyllactosamine. Biological & pharmaceutical bulletin. 1994 Jan; 17(1):29-33. doi: 10.1248/bpb.17.29. [PMID: 7511958]
  • T de Vries, D H van den Eijnden, J Schultz, R O'Neill. Efficient enzymatic synthesis of the sialyl-Lewisx tetrasaccharide. A ligand for selectin-type adhesion molecules. FEBS letters. 1993 Sep; 330(3):243-8. doi: 10.1016/0014-5793(93)80881-t. [PMID: 7690713]
  • U Schumacher, P Vischer, W Völker, B Engelmann. Lectin binding and uptake and glycoprotein characterization of isolated porcine aortic endothelial and smooth muscle cells. Cell biochemistry and function. 1993 Sep; 11(3):225-30. doi: 10.1002/cbf.290110311. [PMID: 8403237]
  • O Hosomi, A Takeya, S Yazawa. A novel lectin in rabbit serum binds H type 1, H type 2 and N-acetyl lactosamine structures. Biochimica et biophysica acta. 1993 May; 1157(1):45-9. doi: 10.1016/0304-4165(93)90076-k. [PMID: 8499478]
  • A Vilkman, R Niemelä, L Penttilä, J Helin, A Leppänen, A Seppo, H Maaheimo, S Lusa, O Renkonen. Elongation of both branches of biantennary backbones of oligo-(N-acetyllactosamino)glycans by human serum (1----3)-N-acetyl-beta-D- glucosaminyltransferase. Carbohydrate research. 1992 Mar; 226(1):155-74. doi: 10.1016/0008-6215(92)84061-v. [PMID: 1386788]
  • F Dall'Olio, N Malagolini, F Serafini-Cessi. Enhanced CMP-NeuAc:Gal beta 1,4GlcNAc-R alpha 2,6 sialyltransferase activity of human colon cancer xenografts in athymic nude mice and of xenograft-derived cell lines. International journal of cancer. 1992 Jan; 50(2):325-30. doi: 10.1002/ijc.2910500227. [PMID: 1730528]
  • A Leppänen, L Penttilä, R Niemelä, J Helin, A Seppo, S Lusa, O Renkonen. Human serum contains a novel beta 1,6-N-acetylglucosaminyltransferase activity that is involved in midchain branching of oligo (N-acetyllactosaminoglycans). Biochemistry. 1991 Sep; 30(38):9287-96. doi: 10.1021/bi00102a022. [PMID: 1832557]
  • R Ramphal, C Carnoy, S Fievre, J C Michalski, N Houdret, G Lamblin, G Strecker, P Roussel. Pseudomonas aeruginosa recognizes carbohydrate chains containing type 1 (Gal beta 1-3GlcNAc) or type 2 (Gal beta 1-4GlcNAc) disaccharide units. Infection and immunity. 1991 Feb; 59(2):700-4. doi: 10.1128/iai.59.2.700-704.1991. [PMID: 1670932]
  • F Dall'Olio, N Malagolini, G Di Stefano, M Ciambella, F Serafini-Cessi. Alpha 2,6 sialylation of N-acetyllactosaminic sequences in human colorectal cancer cell lines. Relationship with non-adherent growth. International journal of cancer. 1991 Jan; 47(2):291-7. doi: 10.1002/ijc.2910470220. [PMID: 1899084]
  • N Malagolini, F Dall'Olio, F Serafini-Cessi, C Cessi. Effect of acute and chronic ethanol administration on rat liver alpha 2,6-sialyltransferase activity responsible for sialylation of serum transferrin. Alcoholism, clinical and experimental research. 1989 Oct; 13(5):649-53. doi: 10.1111/j.1530-0277.1989.tb00398.x. [PMID: 2688463]
  • M N Fukuda, H Sasaki, L Lopez, M Fukuda. Survival of recombinant erythropoietin in the circulation: the role of carbohydrates. Blood. 1989 Jan; 73(1):84-9. doi: NULL. [PMID: 2910371]
  • J M Wieruszeski, J C Michalski, J Montreuil, G Strecker. Sequential 1H and 13C resonance assignments for an octa- and decasaccharide of the N-acetyllactosamine type by multiple-step relayed correlation and heteronuclear correlation nuclear magnetic resonance. Glycoconjugate journal. 1989; 6(2):183-94. doi: 10.1007/bf01050647. [PMID: 2535483]
  • B C Zhu, R A Laine. Purification of acetyllactosamine-specific tomato lectin by erythroglycan-sepharose affinity chromatography. Preparative biochemistry. 1989; 19(4):341-50. doi: 10.1080/10826068908544922. [PMID: 2622874]
  • H Ito, N Latov. Monoclonal IgM in two patients with motor neuron disease bind to the carbohydrate antigens Gal(beta 1-3)GalNAc and Gal(beta 1-3)GlcNAc. Journal of neuroimmunology. 1988 Sep; 19(3):245-53. doi: 10.1016/0165-5728(88)90006-9. [PMID: 2457603]
  • T K Korhonen, K Haahtela, A Pirkola, J Parkkinen. A N-acetyllactosamine-specific cell-binding activity in a plant pathogen, Erwinia rhapontici. FEBS letters. 1988 Aug; 236(1):163-6. doi: 10.1016/0014-5793(88)80307-7. [PMID: 2456952]
  • U Karsten, G Pilgrim, F G Hanisch, G Uhlenbruck, M Kasper, P Stosiek, G Papsdorf, G Pasternak. A new monoclonal antibody (A46-B/B10) highly specific for the blood group H type 2 epitope: generation, epitope analysis, serological and histological evaluation. British journal of cancer. 1988 Aug; 58(2):176-81. doi: 10.1038/bjc.1988.187. [PMID: 2458750]
  • A M Wu, S Sugii, F G Gruezo, E A Kabat. Immunochemical studies on the N-acetyllactosamine beta-(1----6)-linked trisaccharide specificity of Ricinus communis agglutinin. Carbohydrate research. 1988 Jul; 178(?):243-57. doi: 10.1016/0008-6215(88)80116-2. [PMID: 3191508]
  • Y Tsuji, H Clausen, E Nudelman, T Kaizu, S Hakomori, S Isojima. Human sperm carbohydrate antigens defined by an antisperm human monoclonal antibody derived from an infertile woman bearing antisperm antibodies in her serum. The Journal of experimental medicine. 1988 Jul; 168(1):343-56. doi: 10.1084/jem.168.1.343. [PMID: 3294333]
  • C S Foster, A M Neville. Expression of breast epithelial differentiation antigens in human primary breast cancer. Journal of the National Cancer Institute. 1987 Oct; 79(4):613-22. doi: 10.1093/jnci/79.4.613. [PMID: 2443736]
  • E Berman, H Lis. 13C-NMR study of the binding of [1-13C]galactose-labelled N-acetyllactosamine and [1-13C]galactose-enriched hen ovalbumin to soybean agglutinin. Biochimica et biophysica acta. 1987 Jun; 924(3):403-7. doi: 10.1016/0304-4165(87)90154-1. [PMID: 3593758]
  • M Pierce, J Arango. Rous sarcoma virus-transformed baby hamster kidney cells express higher levels of asparagine-linked tri- and tetraantennary glycopeptides containing [GlcNAc-beta (1,6)Man-alpha (1,6)Man] and poly-N-acetyllactosamine sequences than baby hamster kidney cells. The Journal of biological chemistry. 1986 Aug; 261(23):10772-7. doi: 10.1016/s0021-9258(18)67453-8. [PMID: 3015940]
  • C Derappe, C Bauvy, M Lemonnier, M Lhermitte, N Platzer. Isolation and characterization of two sialyloligosaccharides containing N-acetyllactosamine from pregnancy urine. Carbohydrate research. 1986 Jan; 145(2):341-7. doi: 10.1016/s0008-6215(00)90442-7. [PMID: 3955566]
  • E Berman, J H Brown, H Lis, N Sharon. Binding of [1-13C]galactose-labeled N-acetyllactosamine to Erythrina cristagalli agglutinin as studied by 13C-NMR. European journal of biochemistry. 1985 Oct; 152(2):447-51. doi: 10.1111/j.1432-1033.1985.tb09217.x. [PMID: 4054114]
  • J L Iglesias, H Lis, N Sharon. Purification and properties of a D-galactose/N-acetyl-D-galactosamine-specific lectin from Erythrina cristagalli. European journal of biochemistry. 1982 Apr; 123(2):247-52. doi: 10.1111/j.1432-1033.1982.tb19760.x. [PMID: 6978812]
  • H Debray, B Fournet, J Montreuil, L Dorland, F C Vliegenthart. Structure determination by 360-MHz 1H-NMR spectroscopy and methylation analysis of a biantennary glycan of the N-acetyllactosaminic type isolated from rat-liver plasma membrane. European journal of biochemistry. 1981 Apr; 115(3):559-63. doi: 10.1111/j.1432-1033.1981.tb06239.x. [PMID: 7238520]