Lactosamine (BioDeep_00000028248)

   

human metabolite Endogenous


代谢物信息卡片


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

化学式: C12H23NO10 (341.1321898)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C(C1C(C(C(C(O1)OC(C(CO)O)C(C(C=O)N)O)O)O)O)O
InChI: InChI=1S/C12H23NO10/c13-4(1-14)7(18)11(5(17)2-15)23-12-10(21)9(20)8(19)6(3-16)22-12/h1,4-12,15-21H,2-3,13H2/t4-,5+,6+,7+,8-,9-,10+,11+,12-/m0/s1

描述信息

Lactosamine is a disaccharide composed of galactose b1,4-linked to N-acetylglucosamine, and is a common constituent of complex N-linked glycans in metazoans. Unmodified terminal lactosamine, however, is less typical in tissues, since it is often further modified by additional substitutions, such as fucose, sialic acid, or sulfate to form a number of significant receptor and signaling molecules. Lactosamine-containing glycans are also required for proper targeting and maintenance of olfactory axons, and may also function in other sensory regions.(PMID: 17111357).
Isolated from human milk

同义名列表

11 个代谢物同义名

(2R,3R,4S,5R)-2-amino-3,5,6-trihydroxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexanal; (2R,3R,4S,5R)-2-amino-3,5,6-trihydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanal; beta-delta-Galactopyranosyl-(1->4)-2-amino-2-deoxy-delta-glucose; 2-Amino-2-deoxy-4-O-beta-delta-galactopyranosyl-delta-glucose; beta-D-Galactopyranosyl-(1->4)-2-amino-2-deoxy-D-glucose; 2-Amino-2-deoxy-4-O-beta-D-galactopyranosyl-D-glucose; beta-delta-Galactopyranosyl-(1->4)-delta-glucosamine; beta-D-Galactopyranosyl-(1->4)-D-glucosamine; Polylactosamine; Lactosamine; LACN



数据库引用编号

9 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

  • Alexandr B Ryzhikov, Galina S Onkhonova, Ilnaz R Imatdinov, Elena V Gavrilova, Rinat A Maksyutov, Elena A Gordeeva, Galina V Pazynina, Ivan M Ryzhov, Nadezhda V Shilova, Nicolai V Bovin. Recombinant SARS-CoV-2 S Protein Binds to Glycans of the Lactosamine Family in vitro. Biochemistry. Biokhimiia. 2021 Mar; 86(3):243-247. doi: 10.1134/s0006297921030019. [PMID: 33838626]
  • Nandini Mondal, Brad Dykstra, Jungmin Lee, David J Ashline, Vernon N Reinhold, Derrick J Rossi, Robert Sackstein. Distinct human α(1,3)-fucosyltransferases drive Lewis-X/sialyl Lewis-X assembly in human cells. The Journal of biological chemistry. 2018 05; 293(19):7300-7314. doi: 10.1074/jbc.ra117.000775. [PMID: 29593094]
  • Subhash R Rauthu, Tze Chieh Shiao, Sabine André, Michelle C Miller, Élodie Madej, Kevin H Mayo, Hans-Joachim Gabius, René Roy. Defining the potential of aglycone modifications for affinity/selectivity enhancement against medically relevant lectins: synthesis, activity screening, and HSQC-based NMR analysis. Chembiochem : a European journal of chemical biology. 2015 Jan; 16(1):126-39. doi: 10.1002/cbic.201402474. [PMID: 25407851]
  • 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]
  • Bassam Al Atalah, Pierre Rougé, David F Smith, Paul Proost, Yi Lasanajak, Els J M Van Damme. Expression analysis of a type S2 EUL-related lectin from rice in Pichia pastoris. Glycoconjugate journal. 2012 Oct; 29(7):467-79. doi: 10.1007/s10719-012-9405-2. [PMID: 22684190]
  • Wataru Sumiyoshi, Shin-ichi Nakakita, Nobumitsu Miyanishi, Keita Yamada, Kayo Hasehira, Yukari Nakakita, Jun Hirabayashi. Hypersialylated type-I lactosamine-containing N-glycans found in Artiodactyla sera are potential xenoantigens. Glycobiology. 2012 Aug; 22(8):1031-41. doi: 10.1093/glycob/cws069. [PMID: 22492204]
  • Govindasamy Kadirvel, Sergio A Machado, Claudia Korneli, Emily Collins, Paul Miller, Kelsey N Bess, Kazuhiro Aoki, Michael Tiemeyer, Nicolai Bovin, David J Miller. Porcine sperm bind to specific 6-sialylated biantennary glycans to form the oviduct reservoir. Biology of reproduction. 2012 Jun; 87(6):147. doi: 10.1095/biolreprod.112.103879. [PMID: 23115267]
  • Jonas Van Hove, Elke Fouquaert, David F Smith, Paul Proost, Els J M Van Damme. Lectin activity of the nucleocytoplasmic EUL protein from Arabidopsis thaliana. Biochemical and biophysical research communications. 2011 Oct; 414(1):101-5. doi: 10.1016/j.bbrc.2011.09.031. [PMID: 21945438]
  • Maria Kolatsi-Joannou, Karen L Price, Paul J Winyard, David A Long. Modified citrus pectin reduces galectin-3 expression and disease severity in experimental acute kidney injury. PloS one. 2011 Apr; 6(4):e18683. doi: 10.1371/journal.pone.0018683. [PMID: 21494626]
  • Omai B Garner, Hector C Aguilar, Jennifer A Fulcher, Ernest L Levroney, Rebecca Harrison, Lacey Wright, Lindsey R Robinson, Vanessa Aspericueta, Maria Panico, Stuart M Haslam, Howard R Morris, Anne Dell, Benhur Lee, Linda G Baum. Endothelial galectin-1 binds to specific glycans on nipah virus fusion protein and inhibits maturation, mobility, and function to block syncytia formation. PLoS pathogens. 2010 Jul; 6(7):e1000993. doi: 10.1371/journal.ppat.1000993. [PMID: 20657665]
  • Sebastian Kopitzki, Knud J Jensen, Joachim Thiem. Synthesis of benzaldehyde-functionalized glycans: a novel approach towards glyco-SAMs as a tool for surface plasmon resonance studies. Chemistry (Weinheim an der Bergstrasse, Germany). 2010 Jun; 16(23):7017-29. doi: 10.1002/chem.200902693. [PMID: 20432412]
  • Makoto Ogata, Makoto Nakajima, Tatsuya Kato, Takakiyo Obara, Hirokazu Yagi, Koichi Kato, Taichi Usui, Enoch Y Park. Synthesis of sialoglycopolypeptide for potentially blocking influenza virus infection using a rat alpha2,6-sialyltransferase expressed in BmNPV bacmid-injected silkworm larvae. BMC biotechnology. 2009 Jun; 9(?):54. doi: 10.1186/1472-6750-9-54. [PMID: 19500344]
  • Matthew J Stokes, M Lucia S Güther, Daniel C Turnock, Alan R Prescott, Kirstee L Martin, Magnus S Alphey, Michael A J Ferguson. The synthesis of UDP-N-acetylglucosamine is essential for bloodstream form trypanosoma brucei in vitro and in vivo and UDP-N-acetylglucosamine starvation reveals a hierarchy in parasite protein glycosylation. The Journal of biological chemistry. 2008 Jun; 283(23):16147-61. doi: 10.1074/jbc.m709581200. [PMID: 18381290]
  • Harumi Yamamoto, Hiromu Takematsu, Reiko Fujinawa, Yuko Naito, Yasushi Okuno, Gozoh Tsujimoto, Akemi Suzuki, Yasunori Kozutsumi. Correlation index-based responsible-enzyme gene screening (CIRES), a novel DNA microarray-based method for enzyme gene involved in glycan biosynthesis. PloS one. 2007 Nov; 2(11):e1232. doi: 10.1371/journal.pone.0001232. [PMID: 18043739]
  • Víctor García-Aparicio, Matthieu Sollogoub, Yves Blériot, Virginie Colliou, Sabine André, Juan L Asensio, F Javier Cañada, Hans-Joachim Gabius, Pierre Sinaÿ, Jesús Jiménez-Barbero. The conformation of the C-glycosyl analogue of N-acetyl-lactosamine in the free state and bound to a toxic plant agglutinin and human adhesion/growth-regulatory galectin-1. Carbohydrate research. 2007 Sep; 342(12-13):1918-28. doi: 10.1016/j.carres.2007.02.034. [PMID: 17408600]
  • T Kunieda, T Fujiyuki, R Kucharski, S Foret, S A Ament, A L Toth, K Ohashi, H Takeuchi, A Kamikouchi, E Kage, M Morioka, M Beye, T Kubo, G E Robinson, R Maleszka. Carbohydrate metabolism genes and pathways in insects: insights from the honey bee genome. Insect molecular biology. 2006 Oct; 15(5):563-76. doi: 10.1111/j.1365-2583.2006.00677.x. [PMID: 17069632]
  • 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]
  • Yves Allory, Frédéric Commo, Liliane Boccon-Gibod, Mathilde Sibony, Patrice Callard, Pierre Ronco, Hanna Debiec. Sulfated HNK-1 epitope in developing and mature kidney: a new marker for thin ascending loop of Henle and tubular injury in acute tubular necrosis. The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society. 2006 May; 54(5):575-84. doi: 10.1369/jhc.5a6791.2006. [PMID: 16401697]
  • Amandeep Kaur, Sukhdev Singh Kamboj, Jatinder Singh, A K Saxena, Vikram Dhuna. Isolation of a novel N-acetyl-D-lactosamine specific lectin from Alocasia cucullata (Schott.). Biotechnology letters. 2005 Nov; 27(22):1815-20. doi: 10.1007/s10529-005-3559-y. [PMID: 16314976]
  • Hideki Tagawa, Yasuhiko Kizuka, Tomoko Ikeda, Satsuki Itoh, Nana Kawasaki, Hidetake Kurihara, Maristela Lika Onozato, Akihiro Tojo, Tatsuo Sakai, Toshisuke Kawasaki, Shogo Oka. A non-sulfated form of the HNK-1 carbohydrate is expressed in mouse kidney. The Journal of biological chemistry. 2005 Jun; 280(25):23876-83. doi: 10.1074/jbc.m501728200. [PMID: 15843379]
  • R Léonard, S Lhernould, M Carlué, P Fleurat, A Maftah, G Costa. Biochemical characterization of Silene alba alpha4-fucosyltransferase and Lewis a products. Glycoconjugate journal. 2005 Feb; 22(1-2):71-8. doi: 10.1007/s10719-005-0404-4. [PMID: 15864437]
  • Manpreet Kaur, Jatinder Singh, Sukhdev Singh Kamboj, Jagmohan Singh, Amandeep Kaur, S K Sood, A K Saxena. Isolation and characterization of two N-acetyl-D-lactosamine specific lectins from tubers of Arisaema intermedium Blume and A. wallichianum Hook f. Indian journal of biochemistry & biophysics. 2005 Feb; 42(1):34-40. doi: ". [PMID: 23923579]
  • Kate Koles, William McDowell, Radmila Mileusnic, Steven P R Rose. Glycan analysis of the chicken synaptic plasma membrane glycoproteins--a major synaptic N-glycan carries the LewisX determinant. International journal of biological sciences. 2005; 1(4):126-34. doi: 10.7150/ijbs.1.126. [PMID: 16244702]
  • Giuseppina Di Stefano, Marcella Lanza, Felix Kratz, Luca Merina, Luigi Fiume. A novel method for coupling doxorubicin to lactosaminated human albumin by an acid sensitive hydrazone bond: synthesis, characterization and preliminary biological properties of the conjugate. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2004 Dec; 23(4-5):393-7. doi: 10.1016/j.ejps.2004.09.005. [PMID: 15567293]
  • Y C Li, C T Guan, K Q Zhao, Z L Chen, T L Li. Pharmacokinetics of lactosaminated recombinant human growth hormone in mice. Acta pharmacologica Sinica. 2001 May; 22(5):450-4. doi: NULL. [PMID: 11743895]
  • Y Kato, H Onishi, Y Machida. Biological characteristics of lactosaminated N-succinyl-chitosan as a liver-specific drug carrier in mice. Journal of controlled release : official journal of the Controlled Release Society. 2001 Feb; 70(3):295-307. doi: 10.1016/s0168-3659(00)00356-4. [PMID: 11182200]
  • Juha Kirveskari, Timo Paavonen, Pekka Häyry, Risto Renkonen. De novo induction of endothelial L-selectin ligands during kidney allograft rejection. Journal of the American Society of Nephrology : JASN. 2000 Dec; 11(12):2358-2365. doi: 10.1681/asn.v11122358. [PMID: 11095659]
  • M J Filiatrault, B W Gibson, B Schilling, S Sun, R S Munson, A A Campagnari. Construction and characterization of Haemophilus ducreyi lipooligosaccharide (LOS) mutants defective in expression of heptosyltransferase III and beta1,4-glucosyltransferase: identification of LOS glycoforms containing lactosamine repeats. Infection and immunity. 2000 Jun; 68(6):3352-61. doi: 10.1128/iai.68.6.3352-3361.2000. [PMID: 10816485]
  • N Parkhomovskiy, P T Martin. Alpha-galactosidase stimulates acetylcholine receptor aggregation in skeletal muscle cells via PNA-binding carbohydrates. Biochemical and biophysical research communications. 2000 Apr; 270(3):899-902. doi: 10.1006/bbrc.2000.2521. [PMID: 10772922]
  • 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]
  • R P Vanmaele, L D Heerze, G D Armstrong. Role of lactosyl glycan sequences in inhibiting enteropathogenic Escherichia coli attachment. Infection and immunity. 1999 Jul; 67(7):3302-7. doi: 10.1128/iai.67.7.3302-3307.1999. [PMID: 10377105]
  • L Beljaars, K Poelstra, G Molema, D K Meijer. Targeting of sugar- and charge-modified albumins to fibrotic rat livers: the accessibility of hepatic cells after chronic bile duct ligation. Journal of hepatology. 1998 Oct; 29(4):579-88. doi: 10.1016/s0168-8278(98)80153-0. [PMID: 9824267]
  • L Fiume, G Di Stefano, C Busi, A Mattioli, G Battista Gervasi, M Bertini, C Bartoli, R Catalani, G Caccia, C Farina, A Fissi, O Pieroni, R Giuseppetti, E D'Ugo, R Bruni, M Rapicetta. Hepatotropic conjugate of adenine arabinoside monophosphate with lactosaminated poly-L-lysine. Synthesis of the carrier and pharmacological properties of the conjugate. Journal of hepatology. 1997 Feb; 26(2):253-9. doi: 10.1016/s0168-8278(97)80038-4. [PMID: 9059943]
  • M Ferens-Sieczkowska, M Orczyk-Pawiłowicz, B Morawiecka. The N-acetylgalactosamine and lactosamine specific lectin from Iris hybrida leaves. Acta biochimica Polonica. 1997; 44(2):301-7. doi: 10.18388/abp.1997_4425. [PMID: 9360719]
  • C A Palmerini, C Saccardi, A Floridi, G Arienti. Formylcolchicine bound to lactosaminated serum albumin is a more active antifibrotic agent than free colchicine. Clinica chimica acta; international journal of clinical chemistry. 1996 Oct; 254(2):149-57. doi: 10.1016/0009-8981(96)06381-4. [PMID: 8896903]
  • G Di Stefano, C Busi, A Mattioli, L Fiume. Selective delivery to the liver of antiviral nucleoside analogs coupled to a high molecular mass lactosaminated poly-L-lysine and administered to mice by intramuscular route. Biochemical pharmacology. 1995 Jun; 49(12):1769-75. doi: 10.1016/0006-2952(95)00020-z. [PMID: 7541203]
  • P A Romero, T Way, A Herscovics. Lamp-1 does not acquire the large polylactosaminoglycans characteristic of F9 cells. The Biochemical journal. 1993 Nov; 296 ( Pt 1)(?):253-7. doi: 10.1042/bj2960253. [PMID: 8250851]
  • T Kohriyama, R K Yu, C T Berg, J F Poduslo. Sulfate incorporation into peripheral nerve endoneurial glycolipids after crush and permanent transection injury. Journal of neuroscience research. 1990 Jun; 26(2):144-8. doi: 10.1002/jnr.490260203. [PMID: 2366259]
  • B Saunier, C Goulut, F Nato, R Bourrillon. Biosynthesis of high molecular weight polylactosamine-type glycopeptides in rat Zajdela hepatoma ascites cells. Biochimica et biophysica acta. 1989 May; 1011(2-3):110-6. doi: 10.1016/0167-4889(89)90196-1. [PMID: 2713399]
  • F Bernini, D P Via, T M Bocan, A M Gotto, L C Smith. Lactosaminated Fab fragments specific for low density lipoproteins/hepatocyte targeting and hypolipoproteinemic activity. Arteriosclerosis (Dallas, Tex.). 1988 Nov; 8(6):825-31. doi: 10.1161/01.atv.8.6.825. [PMID: 3196227]
  • L Fiume, A Mattioli, C Busi, C Accorsi. Selective penetration and pharmacological activity of lactosaminated albumin conjugates of adenine arabinoside 5-monophosphate (ara-AMP) in mouse liver. Gut. 1984 Dec; 25(12):1392-8. doi: 10.1136/gut.25.12.1392. [PMID: 6210232]
  • L Fiume, C Busi, A Mattioli. Targeting of antiviral drugs by coupling with protein carriers. FEBS letters. 1983 Mar; 153(1):6-10. doi: 10.1016/0014-5793(83)80108-2. [PMID: 6186534]
  • L Fiume, C Busi, A Mattioli. Lactosaminated human serum albumin as hepatotropic drug carrier. Rate of uptake by mouse liver. FEBS letters. 1982 Sep; 146(1):42-6. doi: 10.1016/0014-5793(82)80701-1. [PMID: 7140975]
  • L Fiume, C Busi, A Mattioli, P G Balboni, G Barbanti-Brodano. Hepatocyte targeting of adenine-9-beta-D-arabinofuranoside 5' -monophosphate (ara-AMP) coupled to lactosaminated albumin. FEBS letters. 1981 Jul; 129(2):261-4. doi: 10.1016/0014-5793(81)80179-2. [PMID: 6169548]