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79831-76-8 | Castanospermine
CAS No: 79831-76-8 Catalog No: AG003OPW MDL No:MFCD00017555
Product Description
Catalog Number:
AG003OPW
Chemical Name:
Castanospermine
CAS Number:
79831-76-8
Molecular Formula:
C8H15NO4
Molecular Weight:
189.2090
MDL Number:
MFCD00017555
IUPAC Name:
(1S,6S,7R,8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,6,7,8-tetrol
InChI:
InChI=1S/C8H15NO4/c10-4-1-2-9-3-5(11)7(12)8(13)6(4)9/h4-8,10-13H,1-3H2/t4-,5-,6+,7+,8+/m0/s1
InChI Key:
JDVVGAQPNNXQDW-TVNFTVLESA-N
SMILES:
OC1C(O)CN2C(C1O)C(O)CC2
UNII:
Q0I3184XM7
Properties
Complexity:
201
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
5
Defined Bond Stereocenter Count:
0
Exact Mass:
189.1g/mol
Formal Charge:
0
Heavy Atom Count:
13
Hydrogen Bond Acceptor Count:
5
Hydrogen Bond Donor Count:
4
Isotope Atom Count:
0
Molecular Weight:
189.211g/mol
Monoisotopic Mass:
189.1g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
84.2A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-2.2
Literature
| Title | Journal |
|---|---|
| Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine. | Bioorganic & medicinal chemistry 20121115 |
| Dose- and schedule-dependent protective efficacy of celgosivir in a lethal mouse model for dengue virus infection informs dosing regimen for a proof of concept clinical trial. | Antiviral research 20121001 |
| The effects of Castanospermine, an oligosaccharide processing inhibitor, on mononuclear/endothelial cell binding and the expression of cell adhesion molecules. | Transplant immunology 20120801 |
| Studies on α-glucosidase inhibitors development: magic molecules for the treatment of carbohydrate mediated diseases. | Mini reviews in medicinal chemistry 20120701 |
| Comparison and characterization of α-amylase inducers in Aspergillus nidulans based on nuclear localization of AmyR. | Applied microbiology and biotechnology 20120601 |
| Propagation of RML prions in mice expressing PrP devoid of GPI anchor leads to formation of a novel, stable prion strain. | PLoS pathogens 20120601 |
| Hypericin and pseudohypericin concentrations of a valuable medicinal plant Hypericum perforatum L. are enhanced by arbuscular mycorrhizal fungi. | Mycorrhiza 20120201 |
| Purification and partial biochemical characterization of a membrane-bound type II-like α-glucosidase from the yeast morphotype of Sporothrix schenckii. | Antonie van Leeuwenhoek 20120201 |
| Animal models of dengue virus infection. | Viruses 20120101 |
| Dengue virus entry as target for antiviral therapy. | Journal of tropical medicine 20120101 |
| Folding, quality control, and secretion of pancreatic ribonuclease in live cells. | The Journal of biological chemistry 20110218 |
| The role of alpha-glucosidase in germinating barley grains. | Plant physiology 20110201 |
| Malectin participates in a backup glycoprotein quality control pathway in the mammalian ER. | PloS one 20110101 |
| Impact of clostridial glucosylating toxins on the proteome of colonic cells determined by isotope-coded protein labeling and LC-MALDI. | Proteome science 20110101 |
| Calreticulin controls the rate of assembly of CD1d molecules in the endoplasmic reticulum. | The Journal of biological chemistry 20101203 |
| Diastereoselective nitrenium ion-mediated cyclofunctionalization: total synthesis of (+)-castanospermine. | Organic letters 20101119 |
| Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. | Bioorganic & medicinal chemistry letters 20101101 |
| Novel method for chase analysis of oligosaccharide metabolic error caused by xenobiotics. | Analytical biochemistry 20101001 |
| Inhibition of O-GlcNAcase using a potent and cell-permeable inhibitor does not induce insulin resistance in 3T3-L1 adipocytes. | Chemistry & biology 20100924 |
| A membrane-bound trehalase from Chironomus riparius larvae: purification and sensitivity to inhibition. | Glycobiology 20100901 |
| The action of bromoconduritol on ER glucosidase II. | Bioorganic & medicinal chemistry letters 20100901 |
| Synthesis of N-, S-, and C-glycoside castanospermine analogues with selective neutral alpha-glucosidase inhibitory activity as antitumour agents. | Chemical communications (Cambridge, England) 20100807 |
| A new synthetic access to bicyclic polyhydroxylated alkaloid analogues from pyranosides. | Organic & biomolecular chemistry 20100607 |
| Biological study of the angiogenesis inhibitor N-(8-(3-ethynylphenoxy)octyl-1-deoxynojirimycin. | Chemical biology & drug design 20100601 |
| A flexible approach to azasugars: asymmetric total syntheses of (+)-castanospermine, (+)-7-deoxy-6-epi-castanospermine, and (+)-1-epi-castanospermine. | Chemistry (Weinheim an der Bergstrasse, Germany) 20100517 |
| N-Glycosylation plays a role in protein folding of human UGT1A9. | Biochemical pharmacology 20100415 |
| N-glycan-dependent quality control of the Na,K-ATPase beta(2) subunit. | Biochemistry 20100413 |
| Antiviral therapy for hepatitis C virus: beyond the standard of care. | Viruses 20100401 |
| Glycosidase inhibition: assessing mimicry of the transition state. | Organic & biomolecular chemistry 20100121 |
| QSAR Studies on andrographolide derivatives as α-glucosidase inhibitors. | International journal of molecular sciences 20100101 |
| Comparative therapeutic effects of velaglucerase alfa and imiglucerase in a Gaucher disease mouse model. | PloS one 20100101 |
| The compartmentalisation of phosphorylated free oligosaccharides in cells from a CDG Ig patient reveals a novel ER-to-cytosol translocation process. | PloS one 20100101 |
| Antiangiogenic activity of 2-deoxy-D-glucose. | PloS one 20100101 |
| Disruption of N-linked glycosylation enhances ubiquitin-mediated proteasomal degradation of the human ATP-binding cassette transporter ABCG2. | The FEBS journal 20091201 |
| A concise synthesis of castanospermine by the use of a transannular cyclization. | The Journal of organic chemistry 20091120 |
| Steviamine, a new class of indolizidine alkaloid [(1R,2S,3R,5R,8aR)-3-hydroxy-meth-yl-5-methyl-octa-hydro-indolizine-1,2-diol hydro-bromide]. | Acta crystallographica. Section E, Structure reports online 20091101 |
| Inhibition of the exo-beta-D-glucosaminidase CsxA by a glucosamine-configured castanospermine and an amino-australine analogue. | Organic & biomolecular chemistry 20091021 |
| Single chain variable fragment against nicastrin inhibits the gamma-secretase activity. | The Journal of biological chemistry 20091009 |
| Celgosivir, an alpha-glucosidase I inhibitor for the potential treatment of HCV infection. | Current opinion in investigational drugs (London, England : 2000) 20090801 |
| (3aR,8aS,9S,9aR)-9-Hydroxy-perhydro-furo[3,2-f]indolizin-6-one. | Acta crystallographica. Section E, Structure reports online 20090801 |
| Glycosidase inhibition by ring-modified castanospermine analogues: tackling enzyme selectivity by inhibitor tailoring. | Organic & biomolecular chemistry 20090707 |
| Loss of specific chaperones involved in membrane glycoprotein biosynthesis during the maturation of human erythroid progenitor cells. | The Journal of biological chemistry 20090522 |
| Asymmetric synthesis of (+)-castanospermine through enol ether metathesis-hydroboration/oxidation. | Organic & biomolecular chemistry 20090521 |
| Synthesis of thiohydantoin-castanospermine glycomimetics as glycosidase inhibitors. | The Journal of organic chemistry 20090501 |
| (7R,8R,8aS)-8-Hydr-oxy-7-phenyl-per-hydro-indolizin-3-one. | Acta crystallographica. Section E, Structure reports online 20090401 |
| Promotion of IL-4- and IL-5-dependent differentiation of anti-mu-primed B cells by ascorbic acid 2-glucoside. | Immunology letters 20090221 |
| Substrate specificity of the oxidoreductase ERp57 is determined primarily by its interaction with calnexin and calreticulin. | The Journal of biological chemistry 20090123 |
| Alpha-glucosidase promotes hemozoin formation in a blood-sucking bug: an evolutionary history. | PloS one 20090101 |
| Six host range variants of the xenotropic/polytropic gammaretroviruses define determinants for entry in the XPR1 cell surface receptor. | Retrovirology 20090101 |
| Tetrapisispora phaffii killer toxin is a highly specific beta-glucanase that disrupts the integrity of the yeast cell wall. | Microbial cell factories 20090101 |
| Alternative splicing and transcriptome profiling of experimental autoimmune encephalomyelitis using genome-wide exon arrays. | PloS one 20090101 |
| Divergence of catalytic mechanism within a glycosidase family provides insight into evolution of carbohydrate metabolism by human gut flora. | Chemistry & biology 20081020 |
| Broad-spectrum drugs against viral agents. | International journal of molecular sciences 20080901 |
| The comparative pathology of the glycosidase inhibitors swainsonine, castanospermine, and calystegines A3, B2, and C1 in mice. | Toxicologic pathology 20080701 |
| Inhibition of the glucosyltransferase activity of clostridial Rho/Ras-glucosylating toxins by castanospermine. | FEBS letters 20080625 |
| Synthesis and evaluation of sulfamide-type indolizidines as glycosidase inhibitors. | Bioorganic & medicinal chemistry letters 20080501 |
| Efficient synthesis of (+)-1,8,8a-tri-epi-swainsonine, (+)-1,2-di-epi-lentiginosine, (+)-9a-epi-homocastanospermine and (-)-9-deoxy-9a-epi-homocastanospermine from a D-glucose-derived aziridine carboxylate, and study of their glycosidase inhibitory activities. | Organic & biomolecular chemistry 20080221 |
| Indolizidine and quinolizidine alkaloids. | Natural product reports 20080201 |
| Role of receptor polymorphism and glycosylation in syncytium induction and host range variation of ecotropic mouse gammaretroviruses. | Retrovirology 20080101 |
| Carboazidation of chiral allylsilanes: experimental and theoretical investigations. | Chemistry (Weinheim an der Bergstrasse, Germany) 20080101 |
| Synthesis of 1-deoxy-1-hydroxymethyl- and 1-deoxy-1-epi-hydroxymethyl castanospermine as new potential immunomodulating agents. | Journal of medicinal chemistry 20071101 |
| Indolizidine and quinolizidine alkaloids. | Natural product reports 20070201 |
| Posttranslational N-glycosylation of the hepatitis B virus large envelope protein. | Virology journal 20070101 |
| Vinylogous Mukaiyama aldol reactions with 4-oxy-2-trimethylsilyloxypyrroles: relevance to castanospermine synthesis. | Beilstein journal of organic chemistry 20070101 |
| A divergent asymmetric approach to aza-spiropyran derivative and (1S,8aR)-1-hydroxyindolizidine. | Beilstein journal of organic chemistry 20070101 |
| Asymmetric [2 + 2] cycloaddition: total synthesis of (-)-swainsonine and (+)-6-epicastanospermine. | Organic letters 20061012 |
| Antiviral effects of glycosylation and glucose trimming inhibitors on human parainfluenza virus type 3. | Antiviral research 20061001 |
| Interference with O-glycosylation in RMA lymphoma cells leads to a reduced in vivo growth of the tumor. | International journal of cancer 20060915 |
| Intramolecular 5-endo-trig aminomercuration of beta-hydroxy-gamma-alkenylamines: efficient route to a pyrrolidine ring and its application for the synthesis of (+)-castanospermine and analogues. | The Journal of organic chemistry 20060609 |
| Microsphere-based protease assays and screening application for lethal factor and factor Xa. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501 |
| Characterization of endoplasmic reticulum-associated degradation of a protein S mutant identified in a family of quantitative protein S deficiency. | Thrombosis research 20060101 |
| A novel approach for N-glycosylation studies using detergent extracted microsomes. | Molecular and cellular biochemistry 20051001 |
| Glucose trimming of N-glycan in endoplasmic reticulum is indispensable for the growth of Raphanus sativus seedling (kaiware radish). | Bioscience, biotechnology, and biochemistry 20050701 |
| Novel synthesis of castanospermine and 1-epicastanospermine. | Organic letters 20050623 |
| Combined donor leucocyte administration and immunosuppressive drug treatment for survival of rat heart allografts. | Transplant immunology 20041101 |
| Indolizidine and quinolizidine alkaloids. | Natural product reports 20041001 |
| Conversion of the carbohydrate structures of glycoproteins in roots of Raphanus sativus using several glycosidase inhibitors. | Journal of biochemistry 20041001 |
| Abrogation of insulin-like growth factor-I (IGF-I) and insulin action by mevalonic acid depletion: synergy between protein prenylation and receptor glycosylation pathways. | The Journal of biological chemistry 20040910 |
| The chemistry of castanospermine. Direct oxidation of the tetraacetate to the corresponding gamma-lactam. | Carbohydrate research 20040712 |
| Action of celgosivir (6 O-butanoyl castanospermine) against the pestivirus BVDV: implications for the treatment of hepatitis C. | Antiviral chemistry & chemotherapy 20040501 |
| Discordance of UPR signaling by ATF6 and Ire1p-XBP1 with levels of target transcripts. | Biochemical and biophysical research communications 20040430 |
| Maturation of hepatic lipase. Formation of functional enzyme in the endoplasmic reticulum is the rate-limiting step in its secretion. | The Journal of biological chemistry 20040213 |
| The significance of N-linked glycosylation in pig endogenous retrovirus infectivity. | Biochemical and biophysical research communications 20031017 |
| Indolizidine and quinolizidine alkaloids. | Natural product reports 20031001 |
| Calreticulin promotes folding/dimerization of human lipoprotein lipase expressed in insect cells (sf21). | The Journal of biological chemistry 20030801 |
| The cargo receptor ERGIC-53 is a target of the unfolded protein response. | Biochemical and biophysical research communications 20030516 |
| Selection of a high-energy bioactive conformation of a sulfonium-ion glycosidase inhibitor by the enzyme glucoamylase G2. | Journal of the American Chemical Society 20030514 |
| New synthetic approach to enantiopure bicyclic sulfonium salts: swainsonine analogues. | The Journal of organic chemistry 20030418 |
| N-linked oligosaccharide processing, but not association with calnexin/calreticulin is highly correlated with endoplasmic reticulum-associated degradation of antithrombin Glu313-deleted mutant. | Archives of biochemistry and biophysics 20030315 |
| A deficiency in dolichyl-P-glucose:Glc1Man9GlcNAc2-PP-dolichyl alpha3-glucosyltransferase defines a new subtype of congenital disorders of glycosylation. | The Journal of biological chemistry 20030314 |
| Enhancement of neurite outgrowth in PC12 cells stimulated with cyclic AMP and NGF by 6-acylated ascorbic acid 2-O-alpha-glucosides (6-Acyl-AA-2G), novel lipophilic ascorbate derivatives. | Biological & pharmaceutical bulletin 20030301 |
| EDEM as an acceptor of terminally misfolded glycoproteins released from calnexin. | Science (New York, N.Y.) 20030227 |
| Expression and role of mannose receptor/terminal high-mannose type oligosaccharide on osteoclast precursors during osteoclast formation. | The Journal of endocrinology 20030201 |
| Glycosylation inhibitors and neuraminidase enhance human immunodeficiency virus type 1 binding and neutralization by mannose-binding lectin. | The Journal of general virology 20030201 |
| Role of oligomannosidic N-glycans in the proliferation, adhesion and signalling of C6 glioblastoma cells. | Biochimie 20030101 |
| Purification and biochemical characterization of a soluble alpha-glucosidase from the parasite Entamoeba histolytica. | Antonie van Leeuwenhoek 20030101 |
| Calnexin, calreticulin, and ERp57 cooperate in disulfide bond formation in human CD1d heavy chain. | The Journal of biological chemistry 20021122 |
| Glycosylation processing inhibition by castanospermine prevents experimental autoimmune encephalomyelitis by interference with IL-2 receptor signal transduction. | Journal of neuroimmunology 20021101 |
| Involvement of [beta]-glucans in the wide-spectrum antimicrobial activity of Williopsis saturnus var. mrakii MUCL 41968 killer toxin. | Molecular medicine (Cambridge, Mass.) 20021101 |
| Association of the thyrotropin receptor with calnexin, calreticulin and BiP. Efects on the maturation of the receptor. | European journal of biochemistry 20021001 |
| Isomaltose formed by alpha-glucosidases triggers amylase induction in Aspergillus nidulans. | Current genetics 20021001 |
| The combination of interferon alpha-2b and n-butyl deoxynojirimycin has a greater than additive antiviral effect upon production of infectious bovine viral diarrhea virus (BVDV) in vitro: implications for hepatitis C virus (HCV) therapy. | Antiviral research 20020901 |
| Bioavailability of a series of novel acylated ascorbic acid derivatives, 6-O-acyl-2-O-alpha-D-glucopyranosyl-L-ascorbic acids, as an ascorbic acid supplement in rats and guinea pigs. | Bioscience, biotechnology, and biochemistry 20020801 |
| Perturbation of free oligosaccharide trafficking in endoplasmic reticulum glucosidase I-deficient and castanospermine-treated cells. | The Biochemical journal 20020701 |
| No sizable inhibition of glucose-induced insulin secretion by acarbose and castanospermine. | Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20020701 |
| Inhibition of bacterial alpha-glucosidases by castanospermine in pure cultures and activated sludge. | Applied microbiology and biotechnology 20020601 |
| Biosynthesis and processing of Spodoptera frugiperda alpha-mannosidase III. | Glycobiology 20020601 |
| Calnexin is associated with and induced by overexpressed human complement protein C2. | The Anatomical record 20020501 |
| Interferon-gamma increases the expression of glycosylated CD95 in B-leukemic cells: an inducible model to study the role of glycosylation in CD95-signalling and trafficking. | Cytokine 20020421 |
| Castanospermine-trehazolin hybrids: a new family of glycomimetics with tuneable glycosidase inhibitory properties. | Chemical communications (Cambridge, England) 20020421 |
| N-linked oligosaccharide chains of Sendai virus fusion protein determine the interaction with endoplasmic reticulum molecular chaperones. | FEBS letters 20020227 |
| Chaperone interactions of the metalloproteinase meprin A in the secretory or proteasomal-degradative pathway. | Archives of biochemistry and biophysics 20020115 |
| Synthesis of polyhydroxyindolizidines from 5,6-dihydro-2H-pyran-2-one. | Carbohydrate research 20011207 |
| Differential effect of combined lipase deficiency (cld/cld) on human hepatic lipase and lipoprotein lipase secretion. | Journal of lipid research 20011101 |
| Role of cell surface glycosylation in mediating repair of human airway epithelial cell monolayers. | American journal of physiology. Lung cellular and molecular physiology 20011001 |
| Release of polymannose oligosaccharides from vesicular stomatitis virus G protein during endoplasmic reticulum-associated degradation. | Glycobiology 20011001 |
| The lectin chaperone calnexin utilizes polypeptide-based interactions to associate with many of its substrates in vivo. | The Journal of biological chemistry 20010706 |
| Synthesis of nitrogen analogues of salacinol and their evaluation as glycosidase inhibitors. | Journal of the American Chemical Society 20010704 |
| Monoglucosylated oligomannosides are released during the degradation process of newly synthesized glycoproteins. | The Journal of biological chemistry 20010622 |
| Synthesis of 5-azacastanospermine, a conformationally restricted azafagomine analogue. | Chemistry (Weinheim an der Bergstrasse, Germany) 20010601 |
| Heterologous over-expression of alpha-1,6-fucosyltransferase from Rhizobium sp.: application to the synthesis of the trisaccharide beta-D-GlcNAc(1-->4)-[alpha-L-Fuc-(1-->6)]-D-GLcNAc, study of the acceptor specificity and evaluation of polyhydroxylated indolizidines as inhibitors. | Chemistry (Weinheim an der Bergstrasse, Germany) 20010601 |
| Inhibition of N-linked glycosylation. | Current protocols in immunology 20010501 |
| Allylated monosaccharides as precursors in triple reductive amination strategies: synthesis of castanospermine and swainsonine. | The Journal of organic chemistry 20010309 |
| Characterization of the biosynthesis of human immunodeficiency virus type 1 Env from infected T-cells and the effects of glucose trimming of Env on virion infectivity. | The Journal of biological chemistry 20010223 |
| Rubella virus glycoprotein interaction with the endoplasmic reticulum calreticulin and calnexin. | Archives of virology 20010101 |
| Castanospermine, an oligosaccharide processing inhibitor, reduces both lymphocyte-endothelial cell binding and LFA-1alpha membrane expression. | Transplantation proceedings 20010101 |
| Glycosylation and the cystic fibrosis transmembrane conductance regulator. | Respiratory research 20010101 |
| Strategies for enhancing monoclonal antibody accumulation in plant cell and organ cultures. | Biotechnology progress 20010101 |
| The measles virus (MV) glycoproteins interact with cellular chaperones in the endoplasmic reticulum and MV infection upregulates chaperone expression. | Archives of virology 20010101 |
| Inhibition of alpha-glucosidase I of the glycoprotein-processing enzymes by 6-O-butanoyl castanospermine (MDL 28,574) and its consequences in human immunodeficiency virus-infected T cells. | Antimicrobial agents and chemotherapy 19940801 |
| Inhibition of AIDS virus replication by acemannan in vitro. | Molecular biotherapy 19910901 |
| 6-0-butanoylcastanospermine (MDL 28,574) inhibits glycoprotein processing and the growth of HIVs. | AIDS (London, England) 19910601 |
| Castanospermine vs. its 6-O-butanoyl analog: a comparison of toxicity and antiviral activity in vitro and in vivo. | Journal of acquired immune deficiency syndromes 19910101 |
| Inhibitory effect of novel 1-deoxynojirimycin derivatives on HIV-1 replication. | AIDS (London, England) 19901001 |
| Inhibition of glycoprotein processing and HIV replication by castanospermine analogues. | Annals of the New York Academy of Sciences 19900101 |
| Anti-HIV activity of castanospermine analogues. | Lancet (London, England) 19890527 |
| In vitro evaluation of mismatched double-stranded RNA (ampligen) for combination therapy in the treatment of acquired immunodeficiency syndrome. | AIDS research and human retroviruses 19890401 |
| Synergistic inhibition of human immunodeficiency virus type 1 and type 2 replication in vitro by castanospermine and 3'-azido-3'-deoxythymidine. | Antimicrobial agents and chemotherapy 19890101 |
| Inhibition of HIV replication by amino-sugar derivatives. | FEBS letters 19880912 |
| Inhibition of human immunodeficiency virus syncytium formation and virus replication by castanospermine. | Proceedings of the National Academy of Sciences of the United States of America 19871101 |
| Interference with HIV-induced syncytium formation and viral infectivity by inhibitors of trimming glucosidase. | Nature 19871101 |
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