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24967-27-9

24967-27-9 | D-glycero-D-galacto-Non-2-enonic acid, 5-(acetylamino)-2,6-anhydro-3,5-dideoxy-

CAS No: 24967-27-9 Catalog No: AG002Q0N MDL No:MFCD00057470

Product Description

Catalog Number:
AG002Q0N
Chemical Name:
D-glycero-D-galacto-Non-2-enonic acid, 5-(acetylamino)-2,6-anhydro-3,5-dideoxy-
CAS Number:
24967-27-9
Molecular Formula:
C11H17NO8
Molecular Weight:
291.2546
MDL Number:
MFCD00057470
IUPAC Name:
(2R,3R,4S)-3-acetamido-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
InChI:
InChI=1S/C11H17NO8/c1-4(14)12-8-5(15)2-7(11(18)19)20-10(8)9(17)6(16)3-13/h2,5-6,8-10,13,15-17H,3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,8+,9+,10+/m0/s1
InChI Key:
JINJZWSZQKHCIP-UFGQHTETSA-N
SMILES:
OC[C@H]([C@H]([C@@H]1OC(=C[C@@H]([C@H]1NC(=O)C)O)C(=O)O)O)O
EC Number:
246-550-7

Properties

Complexity:
409  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
0
Exact Mass:
291.095g/mol
Formal Charge:
0
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
6  
Isotope Atom Count:
0
Molecular Weight:
291.256g/mol
Monoisotopic Mass:
291.095g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
157A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-2.5  

Literature

Title Journal
Exploring the interactions of unsaturated glucuronides with influenza virus sialidase. Journal of medicinal chemistry 20121025
Pyrrolidinobenzoic acid inhibitors of influenza virus neuraminidase: the hydrophobic side chain influences type A subtype selectivity. Bioorganic & medicinal chemistry 20120715
Molecular modeling of T. rangeli, T. brucei gambiense, and T. evansi sialidases in complex with the DANA inhibitor. Chemical biology & drug design 20120701
NEU1 and NEU3 sialidase activity expressed in human lung microvascular endothelia: NEU1 restrains endothelial cell migration, whereas NEU3 does not. The Journal of biological chemistry 20120504
Receptor-binding specificity of the human parainfluenza virus type 1 hemagglutinin-neuraminidase glycoprotein. Glycobiology 20120201
Inhibitor selectivity of a new class of oseltamivir analogs against viral neuraminidase over human neuraminidase enzymes. Bioorganic & medicinal chemistry 20110501
Syntheses of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid analogues modified by N-sulfonylamidino groups at the C-4 position and biological evaluation as inhibitors of human parainfluenza virus type 1. Bioorganic & medicinal chemistry 20110401
A single amino acid mutation at position 170 of human parainfluenza virus type 1 fusion glycoprotein induces obvious syncytium formation and caspase-3-dependent cell death. Journal of biochemistry 20110201
Real time enzyme inhibition assays provide insights into differences in binding of neuraminidase inhibitors to wild type and mutant influenza viruses. PloS one 20110101
Inhibition of human neuraminidase 3 (NEU3) by C9-triazole derivatives of 2,3-didehydro-N-acetyl-neuraminic acid. Bioorganic & medicinal chemistry letters 20101215
Carbocycles related to oseltamivir as influenza virus group-1-specific neuraminidase inhibitors. Binding to N1 enzymes in the context of virus-like particles. Journal of medicinal chemistry 20101028
Analogs of zanamivir with modified C4-substituents as the inhibitors against the group-1 neuraminidases of influenza viruses. Bioorganic & medicinal chemistry 20100601
Complexity in influenza virus targeted drug design: interaction with human sialidases. Journal of medicinal chemistry 20100408
'Click chemistry' synthesis of a library of 1,2,3-triazole-substituted galactose derivatives and their evaluation against Trypanosoma cruzi and its cell surface trans-sialidase. Bioorganic & medicinal chemistry 20100401
The effect of neuraminidase blocker on gabazine-induced seizures in rat hippocampus. Fiziolohichnyi zhurnal (Kiev, Ukraine : 1994) 20100101
Human sialidase inhibitors: design, synthesis, and biological evaluation of 4-acetamido-5-acylamido-2-fluoro benzoic acids. Bioorganic & medicinal chemistry 20090701
Efficient method for the preparation of peracetylated Neu5Ac2en by flash vacuum pyrolysis. The Journal of organic chemistry 20090605
Sialic acid: a preventable signal for pneumococcal biofilm formation, colonization, and invasion of the host. The Journal of infectious diseases 20090515
Discovery of novel inhibitors of Trypanosoma cruzi trans-sialidase from in silico screening. Bioorganic & medicinal chemistry letters 20090201
Crystal structure of the NanB sialidase from Streptococcus pneumoniae. Journal of molecular biology 20081212
Limited inhibitory effects of oseltamivir and zanamivir on human sialidases. Antimicrobial agents and chemotherapy 20081001
Structure of the catalytic domain of Streptococcus pneumoniae sialidase NanA. Acta crystallographica. Section F, Structural biology and crystallization communications 20080901
2-Deoxy-2,3-didehydro-N-acetylneuraminic acid analogs structurally modified by thiocarbamoylalkyl groups at the C-4 position: Synthesis and biological evaluation as inhibitors of human parainfluenza virus type 1. Bioorganic & medicinal chemistry 20080715
Membrane type sialidase inhibits the megakaryocytic differentiation of human leukemia K562 cells. Biochimica et biophysica acta 20080501
Investigation into an efficient synthesis of 2,3-dehydro-N-acetyl neuraminic acid leads to three decarboxylated sialic acid dimers. Carbohydrate research 20080407
Photoaffinity labeling of sialidase with a biotin-conjugated phenylaminodiazirine derivative of 2,3-didehydro-2-deoxy-N-acetylneuraminic acid. Biological & pharmaceutical bulletin 20080301
Design, synthesis, and biological evaluation of human sialidase inhibitors. Part 1: selective inhibitors of lysosomal sialidase (NEU1). Bioorganic & medicinal chemistry letters 20080115
Sialidase activity in Mycoplasma synoviae. Avian diseases 20071201
Role of sialidase in Mycoplasma alligatoris-induced pulmonary fibroblast apoptosis. Veterinary microbiology 20070331
Synthesis and evaluation of 4-O-alkylated 2-deoxy-2,3-didehydro-N-acetylneuraminic acid derivatives as inhibitors of human parainfluenza virus type-3 sialidase activity. Bioorganic & medicinal chemistry letters 20070315
STD NMR spectroscopy and molecular modeling investigation of the binding of N-acetylneuraminic acid derivatives to rhesus rotavirus VP8* core. Glycobiology 20070101
2-Deoxy-2,3-didehydro-N-acetylneuraminic acid analogues structurally modified at the C-4 position: synthesis and biological evaluation as inhibitors of human parainfluenza virus type 1. Bioorganic & medicinal chemistry 20061201
Preparation of a fluorous protecting group and its application to the chemoenzymatic synthesis of sialidase inhibitor. Chemical communications (Cambridge, England) 20060807
Insights from modeling the 3D structure of H5N1 influenza virus neuraminidase and its binding interactions with ligands. Biochemical and biophysical research communications 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
A QSAR study on influenza neuraminidase inhibitors. Bioorganic & medicinal chemistry 20060215
Structural analysis of a designed inhibitor complexed with the hemagglutinin-neuraminidase of Newcastle disease virus. Glycoconjugate journal 20060201
A sialidase mutant displaying trans-sialidase activity. Journal of molecular biology 20050128
Crystal structure of the human cytosolic sialidase Neu2. Evidence for the dynamic nature of substrate recognition. The Journal of biological chemistry 20050107
Reduction in the adherence of Pseudomonas aeruginosa to human buccal epithelial cells with neuraminidase inhibition. Polish journal of microbiology 20050101
Structural analogs of sialic acid interfere with the binding of erythrocyte binding antigen-175 to glycophorin A, an interaction crucial for erythrocyte invasion by Plasmodium falciparum. Molecular and biochemical parasitology 20041101
Sialic acid recognition by Vibrio cholerae neuraminidase. The Journal of biological chemistry 20040924
Saturation transfer difference (STD) 1H-NMR experiments and in silico docking experiments to probe the binding of N-acetylneuraminic acid and derivatives to Vibrio cholerae sialidase. Proteins 20040801
Localization of sialidase-positive cells expressing Mac-1 and immunoglobulin in the mouse thymus. Glycoconjugate journal 20040101
Investigation of neuraminidase-substrate recognition using molecular dynamics and free energy calculations. Journal of medicinal chemistry 20031218
Inhibition of influenza A virus sialidase activity by sulfatide. FEBS letters 20031023
Oxochromium(V) species formed with 2,3-dehydro-2-deoxy-N-acetylneuraminic or N-acetylneuraminic (sialic) acids: an in vitro model system of oxochromium(V) species potentially stabilized in the respiratory tract upon inhalation of carcinogenic chromium(VI) compounds. Chemical research in toxicology 20030701
The high resolution structures of free and inhibitor-bound Trypanosoma rangeli sialidase and its comparison with T. cruzi trans-sialidase. Journal of molecular biology 20030124
Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives. Bioorganic & medicinal chemistry letters 20020805
Synthesis and anti-influenza evaluation of polyvalent sialidase inhibitors bearing 4-guanidino-Neu5Ac2en derivatives. Bioorganic & medicinal chemistry letters 20020805
Computational 3-D modeling and site-directed mutation of an antibody that binds Neu2en5Ac, a transition state analogue of a sialic acid. Proteins 20011201
Thermal stability of the hemagglutinin-neuraminidase from Sendai virus evidences two folding domains. FEBS letters 20010420
Analysis of inhibitor binding in influenza virus neuraminidase. Protein science : a publication of the Protein Society 20010401
Inhibition of human parainfluenza virus type 1 sialidase by analogs of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid. Glycoconjugate journal 20010401
Synthesis of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid analogues modified at the C-4 and C-9 positions and their behaviour towards sialidase from influenza virus and pig liver membrane. Carbohydrate research 20010115
BCX-1812 (RWJ-270201): discovery of a novel, highly potent, orally active, and selective influenza neuraminidase inhibitor through structure-based drug design. Journal of medicinal chemistry 20000921
A novel approach to antiviral therapy for influenza. The Journal of antimicrobial chemotherapy 19991101
Potent inhibition of influenza sialidase by a benzoic acid containing a 2-pyrrolidinone substituent. Journal of medicinal chemistry 19990701
Dihydropyrancarboxamides related to zanamivir: a new series of inhibitors of influenza virus sialidases. 2. Crystallographic and molecular modeling study of complexes of 4-amino-4H-pyran-6-carboxamides and sialidase from influenza virus types A and B. Journal of medicinal chemistry 19980312
Design and synthesis of benzoic acid derivatives as influenza neuraminidase inhibitors using structure-based drug design. Journal of medicinal chemistry 19971205
A study of the active site of influenza virus sialidase: an approach to the rational design of novel anti-influenza drugs. Journal of medicinal chemistry 19960119
Structure-based inhibitors of influenza virus sialidase. A benzoic acid lead with novel interaction. Journal of medicinal chemistry 19950818
Structures of aromatic inhibitors of influenza virus neuraminidase. Biochemistry 19950314
4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid is a highly effective inhibitor both of the sialidase (neuraminidase) and of growth of a wide range of influenza A and B viruses in vitro. Antimicrobial agents and chemotherapy 19930701
Rational design of potent sialidase-based inhibitors of influenza virus replication. Nature 19930603

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