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LewisYtetrasaccharide

CAS No.:
82993-43-9
Catalog Number:
AG00G5A2
Molecular Formula:
Molecular Weight:
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Purity
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Product Description
Catalog Number:
AG00G5A2
Chemical Name:
LewisYtetrasaccharide
CAS Number:
82993-43-9
MDL Number:
MFCD00797615
IUPAC Name:
N-[(3R,4R,5S,6R)-5-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]acetamide
InChI:
InChI=1S/C26H45NO19/c1-6-12(31)15(34)18(37)24(40-6)45-21-11(27-8(3)30)23(39)42-10(5-29)20(21)44-26-22(17(36)14(33)9(4-28)43-26)46-25-19(38)16(35)13(32)7(2)41-25/h6-7,9-26,28-29,31-39H,4-5H2,1-3H3,(H,27,30)/t6-,7-,9-,10-,11-,12+,13+,14+,15+,16+,17+,18-,19-,20-,21-,22-,23?,24-,25-,26+/m1/s1
InChI Key:
SRHNADOZAAWYLV-MVSAILQPSA-N
Properties
Complexity:
997  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
19  
Defined Bond Stereocenter Count:
0
Exact Mass:
675.259g/mol
Formal Charge:
0
Heavy Atom Count:
46  
Hydrogen Bond Acceptor Count:
19  
Hydrogen Bond Donor Count:
12  
Isotope Atom Count:
0
Molecular Weight:
675.634g/mol
Monoisotopic Mass:
675.259g/mol
Rotatable Bond Count:
9  
Topological Polar Surface Area:
316A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
-6.9  
Literature
Title Journal
Differential glycosylation of MUC1 and CEACAM5 between normal mucosa and tumour tissue of colon cancer patients. International journal of cancer 20120701
Expression of the tumor markers sialyl Lewis A, sialyl Lewis X, Lewis Y, Thomsen-Friedenreich antigen, galectin-1 and galectin-3 in human osteoblasts in vitro. Anticancer research 20120501
Expression of the carbohydrate tumour marker Sialyl Lewis A, Sialyl Lewis X, Lewis Y and Thomsen-Friedenreich antigen in normal squamous epithelium of the uterine cervix, cervical dysplasia and cervical cancer. Histology and histopathology 20120401
Structure of the lectin regulatory domain of the cholesterol-dependent cytolysin lectinolysin reveals the basis for its lewis antigen specificity. Structure (London, England : 1993) 20120208
Lewis y regulate cell cycle related factors in ovarian carcinoma cell RMG-I in vitro via ERK and Akt signaling pathways. International journal of molecular sciences 20120101
Interaction of Helicobacter pylori with C-type lectin dendritic cell-specific ICAM grabbing nonintegrin. Journal of biomedicine & biotechnology 20120101
Studies on the synthesis of Lewis-y oligosaccharides. Carbohydrate research 20111018
Lectin activity of the nucleocytoplasmic EUL protein from Arabidopsis thaliana. Biochemical and biophysical research communications 20111014
Difucosylated oligosaccharide Lewis Y is contained within integrin αvβ3 on RL95-2 cells and required for endometrial receptivity. Fertility and sterility 20110315
Enhancive effects of Lewis y antigen on CD44-mediated adhesion and spreading of human ovarian cancer cell line RMG-I. Journal of experimental & clinical cancer research : CR 20110101
Study on the expression and clinical significances of lewis y antigen and integrin αv, β3 in epithelial ovarian tumors. International journal of molecular sciences 20110101
The stimulation of IGF-1R expression by Lewis(y) antigen provides a powerful development mechanism of epithelial ovarian carcinoma. International journal of molecular sciences 20110101
Increase in docetaxel-resistance of ovarian carcinoma-derived RMG-1 cells with enhanced expression of Lewis Y antigen. International journal of molecular sciences 20110101
Expression and correlation of Lewis y antigen and integrins α5 and β1 in ovarian serous and mucinous carcinoma. International journal of gynecological cancer : official journal of the International Gynecological Cancer Society 20101201
Removal of the outer Kdo from Helicobacter pylori lipopolysaccharide and its impact on the bacterial surface. Molecular microbiology 20101101
Effects of Lewis Y antigen on the gene expression of multiple drug resistance-associated proteins in human ovarian cancer RMG-I-H cells. Medical oncology (Northwood, London, England) 20100901
Enhancement of the adhesive and spreading potentials of ovarian carcinoma RMG-1 cells due to increased expression of integrin alpha5beta1 with the Lewis Y-structure on transfection of the alpha1,2-fucosyltransferase gene. Biochimie 20100701
Gene-modified T cells as immunotherapy for multiple myeloma and acute myeloid leukemia expressing the Lewis Y antigen. Gene therapy 20100501
Lewis(y) antigen stimulates the growth of ovarian cancer cells via regulation of the epidermal growth factor receptor pathway. Oncology reports 20100301
Lewis (y) antigen overexpression increases the expression of MMP-2 and MMP-9 and invasion of human ovarian cancer cells. International journal of molecular sciences 20100101
Lewis Y promotes growth and adhesion of ovarian carcinoma-derived RMG-I cells by upregulating growth factors. International journal of molecular sciences 20100101
Host-dependent Lewis (Le) antigen expression in Helicobacter pylori cells recovered from Leb-transgenic mice. The Journal of experimental medicine 20091221
Phase I biodistribution and pharmacokinetic study of Lewis Y-targeting immunoconjugate CMD-193 in patients with advanced epithelial cancers. Clinical cancer research : an official journal of the American Association for Cancer Research 20091101
Differential recognition and hydrolysis of host carbohydrate antigens by Streptococcus pneumoniae family 98 glycoside hydrolases. The Journal of biological chemistry 20090918
Complex N-glycans or core 1-derived O-glycans are not required for the expression of stage-specific antigens SSEA-1, SSEA-3, SSEA-4, or Le(Y) in the preimplantation mouse embryo. Glycoconjugate journal 20090401
Glycomics and proteomics analyses of mouse uterine luminal fluid revealed a predominance of Lewis Y and X epitopes on specific protein carriers. Molecular & cellular proteomics : MCP 20090201
Breast cancer humoral immune response: involvement of Lewis y through the detection of circulating immune complexes and association with Mucin 1 (MUC1). Journal of experimental & clinical cancer research : CR 20090101
Is there a link between the lipopolysaccharide of Helicobacter pylori gastric MALT lymphoma associated strains and lymphoma pathogenesis? PloS one 20090101
A possible role for metallic ions in the carbohydrate cluster recognition displayed by a Lewis Y specific antibody. PloS one 20090101
Helicobacter pylori lipopolysaccharide modification, Lewis antigen expression, and gastric colonization are cholesterol-dependent. BMC microbiology 20090101
Lewis y antigen promotes the proliferation of ovarian carcinoma-derived RMG-I cells through the PI3K/Akt signaling pathway. Journal of experimental & clinical cancer research : CR 20090101
Relevance of fucosylation and Lewis antigen expression in the bacterial gastroduodenal pathogen Helicobacter pylori. Carbohydrate research 20080811
Disulfide bond bridged divalent antibody-toxin, (Fab-PE38fl)2, with the toxin PE38 fused to the light chain. Journal of microbiology and biotechnology 20080801
Characterization of a streptococcal cholesterol-dependent cytolysin with a lewis y and b specific lectin domain. Biochemistry 20080708
Studies of Lewis antigens and H. pylori adhesion in CHO cell lines engineered to express Lewis b determinants. Glycobiology 20080701
[Transfection of alpha1, 2-fucosyltransferase gene increases the antigenic expression of Lewis y in ovarian cancer cell line RMG-I]. Zhongguo yi xue ke xue yuan xue bao. Acta Academiae Medicinae Sinicae 20080601
Analysis of Helicobacter pylori isolates from Chile: occurrence of selective type 1 Lewis b antigen expression in lipopolysaccharide. Journal of medical microbiology 20080501
DC-SIGN mediates adhesion and rolling of dendritic cells on primary human umbilical vein endothelial cells through LewisY antigen expressed on ICAM-2. Molecular immunology 20080401
Involvement of alpha 1-2-fucosyltransferase I (FUT1) and surface-expressed Lewis(y) (CD174) in first endothelial cell-cell contacts during angiogenesis. Journal of cellular physiology 20080401
Suppression of FUT1/FUT4 expression by siRNA inhibits tumor growth. Biochimica et biophysica acta 20080201
Expression of bisecting type and Lewisx/Lewisy terminated N-glycans on human sperm. The Journal of biological chemistry 20071214
Targeting Lewis Y (Le(y)) in small cell lung cancer with a humanized monoclonal antibody, hu3S193: a pilot trial testing two dose levels. Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20071001
Radioimmunotherapy with alpha-particle emitting 213Bi-C-functionalized trans-cyclohexyl-diethylenetriaminepentaacetic acid-humanized 3S193 is enhanced by combination with paclitaxel chemotherapy. Clinical cancer research : an official journal of the American Association for Cancer Research 20070915
Expression of the blood-group-related antigens Sialyl Lewis a, Sialyl Lewis x and Lewis y in term placentas of normal, preeclampsia, IUGR- and HELLP-complicated pregnancies. Histochemistry and cell biology 20070701
Analysis of lysine clipping of a humanized Lewis-Y specific IgG antibody and its relation to Fc-mediated effector function. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070601
A phase I biodistribution and pharmacokinetic trial of humanized monoclonal antibody Hu3s193 in patients with advanced epithelial cancers that express the Lewis-Y antigen. Clinical cancer research : an official journal of the American Association for Cancer Research 20070601
Virus-induced transcriptional activation of host FUT genes associated with neo-expression of Ley in cytomegalovirus-infected and sialyl-Lex in varicella-zoster virus-infected diploid human cells. Glycobiology 20070401
A monoclonal antibody to Lewis Y/Lewis b revealing mimicry of the histone H1 to carbohydrate structures. Scandinavian journal of immunology 20070401
Adhesion of Candida albicans to HeLa cells: studies using polystyrene beads. Biological & pharmaceutical bulletin 20070301
Preparation of multifunctional glyconanoparticles as a platform for potential carbohydrate-based anticancer vaccines. Carbohydrate research 20070226
Overexpression of fucosyltransferase IV in A431 cell line increases cell proliferation. The international journal of biochemistry & cell biology 20070101
Expression of the carbohydrate tumour marker SLeX, SLeA (CA19-9), LeY and Thomsen-Friedenreich (TF) antigen on normal squamous epithelial tissue of the penis and vagina. Anticancer research 20070101
Lewis(y) antigen (CD174) and apoptosis in gastric and colorectal carcinomas: correlations with clinical and prognostic parameters. Histology and histopathology 20060501
[Genetic diagnosis of H. pylori infection]. Nihon rinsho. Japanese journal of clinical medicine 20051201
Enhanced efficacy of radioimmunotherapy with 90Y-CHX-A''-DTPA-hu3S193 by inhibition of epidermal growth factor receptor (EGFR) signaling with EGFR tyrosine kinase inhibitor AG1478. Clinical cancer research : an official journal of the American Association for Cancer Research 20051001
Synthesis of selected LeY and KH-1 analogues: a medicinal chemistry approach to vaccine optimization. The Journal of organic chemistry 20050429
Clinical evaluation of BR96 sFv-PE40 immunotoxin therapy in canine models of spontaneously occurring invasive carcinoma. Clinical cancer research : an official journal of the American Association for Cancer Research 20050115
A single-step method for the production of sugar hydrazides: intermediates for the chemoselective preparation of glycoconjugates. Bioconjugate chemistry 20050101
High expression of Lewis y/b antigens is associated with decreased survival in lymph node negative breast carcinomas. Breast cancer research : BCR 20050101
The immunogenicity of the tumor-associated antigen Lewis(y) may be suppressed by a bifunctional cross-linker required for coupling to a carrier protein. Chemistry (Weinheim an der Bergstrasse, Germany) 20040719
Lectin receptors for endometrial H-type 1 antigen on goat conceptuses. American journal of reproductive immunology (New York, N.Y. : 1989) 20040701
Antibody-targeted chemotherapy with the calicheamicin conjugate hu3S193-N-acetyl gamma calicheamicin dimethyl hydrazide targets Lewisy and eliminates Lewisy-positive human carcinoma cells and xenografts. Clinical cancer research : an official journal of the American Association for Cancer Research 20040701
Expression of cell surface Lewis X and Y antigens and FUT4 mRNA is increased in Jurkat cells undergoing apoptosis. Biochimica et biophysica acta 20040611
Kaposiform hemangioendothelioma: a study of 33 cases emphasizing its pathologic, immunophenotypic, and biologic uniqueness from juvenile hemangioma. The American journal of surgical pathology 20040501
Killing of target cells by redirected granzyme B in the absence of perforin. FEBS letters 20040326
Antibodies directed against Lewis-Y antigen inhibit signaling of Lewis-Y modified ErbB receptors. Cancer research 20040201
Lewis antigen expression in gastric mucosa of children: relationship with Helicobacter pylori infection. Journal of pediatric gastroenterology and nutrition 20040101
Host gastric Lewis expression determines the bacterial density of Helicobacter pylori in babA2 genopositive infection. Gut 20030701
Expression of glycolipids bearing Lewis phenotypes in tissues and cultured cells of human gynecological cancers. Japanese journal of cancer research : Gann 20021001
The expression of free oligosaccharides in human seminal plasma. The Journal of biological chemistry 20020906
Constructing an adenocarcinoma vaccine: immunization of mice with synthetic KH-1 nonasaccharide stimulates anti-KH-1 and anti-Le(y) antibodies. International journal of cancer 20020510
[Effects of Lewis Y oligosaccharide on secretion and gene expression of EGF and EGF-R in mouse embryos]. Sheng wu hua xue yu sheng wu wu li xue bao Acta biochimica et biophysica Sinica 20020501
Phenotypic variation in molecular mimicry between Helicobacter pylori lipopolysaccharides and human gastric epithelial cell surface glycoforms. Acid-induced phase variation in Lewis(x) and Lewis(y) expression by H. Pylori lipopolysaccharides. The Journal of biological chemistry 20020222
Cathepsin B-labile dipeptide linkers for lysosomal release of doxorubicin from internalizing immunoconjugates: model studies of enzymatic drug release and antigen-specific in vitro anticancer activity. Bioconjugate chemistry 20020101
Congenital nonprogressive hemangioma: a distinct clinicopathologic entity unlike infantile hemangioma. Archives of dermatology 20011201
Ley glycolipid-recognizing monoclonal antibody inhibits procoagulant activity and metastasis of human adenocarcinoma. International journal of oncology 20011101
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Increased expression of the blood group-related Lewis Y antigen on synovial fluid granulocytes of patients with arthritic joint diseases. Rheumatology (Oxford, England) 20010901
Selective tumor sensitization to taxanes with the mAb-drug conjugate cBR96-doxorubicin. International journal of cancer 20010815
Lewis antigen expression by Helicobacter pylori. The Journal of infectious diseases 20010801
The fucosylated histo-blood group antigens H type 2 (blood group O, CD173) and Lewis Y (CD174) are expressed on CD34+ hematopoietic progenitors but absent on mature lymphocytes. Glycobiology 20010801
Construction, expression and characterisation of a single-chain diabody derived from a humanised anti-Lewis Y cancer targeting antibody using a heat-inducible bacterial secretion vector. Cancer immunology, immunotherapy : CII 20010701
Regulation of differentiation- and proliferation-inducers on Lewis antigens, alpha-fucosyltransferase and metastatic potential in hepatocarcinoma cells. British journal of cancer 20010601
A unique microvascular phenotype shared by juvenile hemangiomas and human placenta. Archives of dermatology 20010501
A comparison of Lewis x and Lewis y expression in Helicobacter pylori obtained from children and adults. The Journal of infectious diseases 20010401
Biodistribution properties of (111)indium-labeled C-functionalized trans-cyclohexyl diethylenetriaminepentaacetic acid humanized 3S193 diabody and F(ab')(2) constructs in a breast carcinoma xenograft model. Clinical cancer research : an official journal of the American Association for Cancer Research 20010401
Pursuit of optimal carbohydrate-based anticancer vaccines: preparation of a multiantigenic unimolecular glycopeptide containing the Tn, MBr1, and Lewis(y) antigens. Journal of the American Chemical Society 20010307
Influence of cytokines, monoclonal antibodies and chemotherapeutic drugs on epithelial cell adhesion molecule (EpCAM) and LewisY antigen expression. Clinical and experimental immunology 20010101
Schistosoma mansoni cercarial glycolipids are dominated by Lewis X and pseudo-Lewis Y structures. Glycobiology 20000101
Are autoantibodies against Lewis antigens involved in the pathogenesis of Helicobacter pylori-induced peptic ulcers? Microbiology and immunology 19990101
Lack of correlation between Lewis antigen expression by Helicobacter pylori and gastric epithelial cells in infected patients. Gastroenterology 19981101
Expression of alpha-1,3-galactose and other type 2 oligosaccharide structures in a porcine endothelial cell line transfected with human alpha-1,2-fucosyltransferase cDNA. The Journal of biological chemistry 19970912
The x-ray structure of an anti-tumour antibody in complex with antigen. Nature structural biology 19950601
Properties