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10149-14-1 | D-manno-2-Octulosonic acid, 3-deoxy-
CAS No: 10149-14-1 Catalog No: AG0004LX MDL No:
Product Description
Catalog Number:
AG0004LX
Chemical Name:
D-manno-2-Octulosonic acid, 3-deoxy-
CAS Number:
10149-14-1
Molecular Formula:
C8H14O8
Molecular Weight:
238.1920
IUPAC Name:
(4R,5R,6R,7R)-4,5,6,7,8-pentahydroxy-2-oxooctanoic acid
InChI:
InChI=1S/C8H14O8/c9-2-5(12)7(14)6(13)3(10)1-4(11)8(15)16/h3,5-7,9-10,12-14H,1-2H2,(H,15,16)/t3-,5-,6-,7-/m1/s1
InChI Key:
KYQCXUMVJGMDNG-SHUUEZRQSA-N
SMILES:
OC[C@H]([C@H]([C@@H]([C@@H](CC(=O)C(=O)O)O)O)O)O
UNII:
ZWK96OG89F
Properties
Complexity:
252
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
4
Defined Bond Stereocenter Count:
0
Exact Mass:
238.069g/mol
Formal Charge:
0
Heavy Atom Count:
16
Hydrogen Bond Acceptor Count:
8
Hydrogen Bond Donor Count:
6
Isotope Atom Count:
0
Molecular Weight:
238.192g/mol
Monoisotopic Mass:
238.069g/mol
Rotatable Bond Count:
7
Topological Polar Surface Area:
156A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-3.6
Literature
| Title | Journal |
|---|---|
| The origin of 8-amino-3,8-dideoxy-D-manno-octulosonic acid (Kdo8N) in the lipopolysaccharide of Shewanella oneidensis. | The Journal of biological chemistry 20130329 |
| Exploring the cross-reactivity of S25-2: complex with a 5,6-dehydro-Kdo disaccharide. | Acta crystallographica. Section F, Structural biology and crystallization communications 20130101 |
| Synthesis and immunomodulatory activities of Helicobacter pylori lipophilic terminus of lipopolysaccharide including lipid A. | Carbohydrate research 20120715 |
| The lipopolysaccharide from Capnocytophaga canimorsus reveals an unexpected role of the core-oligosaccharide in MD-2 binding. | PLoS pathogens 20120501 |
| Structure of the O-antigen polysaccharide present in the lipopolysaccharide of Cronobacter dublinensis (subspecies lactaridi or lausannensis) HPB 3169. | Canadian journal of microbiology 20120401 |
| Phosphorylcholine allows for evasion of bactericidal antibody by Haemophilus influenzae. | PLoS pathogens 20120301 |
| Benzyl benzoate glycoside and 3-deoxy-D-manno-2-octulosonic acid derivatives from Solidago decurrens. | Journal of natural products 20120127 |
| The Synthesis and Origin of the Pectic Polysaccharide Rhamnogalacturonan II - Insights from Nucleotide Sugar Formation and Diversity. | Frontiers in plant science 20120101 |
| Characterization of Arabidopsis CTP:3-deoxy-D-manno-2-octulosonate cytidylyltransferase (CMP-KDO synthetase), the enzyme that activates KDO during rhamnogalacturonan II biosynthesis. | Plant & cell physiology 20111001 |
| Structures and genetics of Kdo-containing O-antigens of Cronobacter sakazakii G2706 and G2704, the reference strains of serotypes O5 and O6. | Carbohydrate research 20110927 |
| Characterization of the carbohydrate backbone of Vibrio parahaemolyticus O6 lipopolysaccharides. | Microbiology and immunology 20110801 |
| Structural diversity of the core oligosaccharide domain of Pseudomonas aeruginosa lipopolysaccharide. | Biochemistry. Biokhimiia 20110701 |
| Modulation of substrate specificities of D-sialic acid aldolase through single mutations of Val-251. | The Journal of biological chemistry 20110422 |
| Targeting bacterial membranes: identification of Pseudomonas aeruginosa D-arabinose-5P isomerase and NMR characterisation of its substrate recognition and binding properties. | Chembiochem : a European journal of chemical biology 20110321 |
| New targets for antibacterial design: Kdo biosynthesis and LPS machinery transport to the cell surface. | Current medicinal chemistry 20110101 |
| Biofilm development on Caenorhabditis elegans by Yersinia is facilitated by quorum sensing-dependent repression of type III secretion. | PLoS pathogens 20110101 |
| Exploring the metabolic network of the epidemic pathogen Burkholderia cenocepacia J2315 via genome-scale reconstruction. | BMC systems biology 20110101 |
| Conjugation of LPS-derived oligosaccharides to proteins using oxime chemistry. | Methods in molecular biology (Clifton, N.J.) 20110101 |
| Evidence for a two-metal-ion mechanism in the cytidyltransferase KdsB, an enzyme involved in lipopolysaccharide biosynthesis. | PloS one 20110101 |
| Bacteriophage-resistant mutants in Yersinia pestis: identification of phage receptors and attenuation for mice. | PloS one 20110101 |
| An experimentally-supported genome-scale metabolic network reconstruction for Yersinia pestis CO92. | BMC systems biology 20110101 |
| Kdo: a critical monosaccharide for bacteria viability. | Natural product reports 20101101 |
| Biochemical and immunocytological characterizations of Arabidopsis pollen tube cell wall. | Plant physiology 20100801 |
| Characterization of a putative 3-deoxy-D-manno-2-octulosonic acid (Kdo) transferase gene from Arabidopsis thaliana. | Glycobiology 20100501 |
| Complete genome sequence of Thermocrinis albus type strain (HI 11/12). | Standards in genomic sciences 20100430 |
| Sialic acid-containing lipopolysaccharides of Salmonella O48 strains--potential role in camouflage and susceptibility to the bactericidal effect of normal human serum. | Microbial ecology 20100401 |
| Diversity of non-stoichiometric substitutions on the lipopolysaccharide of E. coli C demonstrated by electrospray ionization single quadrupole mass spectrometry. | Rapid communications in mass spectrometry : RCM 20100101 |
| Genetic analysis of the Staphylococcus epidermidis macromolecular synthesis operon: Serp1129 is an ATP binding protein and sigA transcription is regulated by both sigma(A)- and sigma(B)-dependent promoters. | BMC microbiology 20100101 |
| Genome sequence of Cronobacter sakazakii BAA-894 and comparative genomic hybridization analysis with other Cronobacter species. | PloS one 20100101 |
| Importance of Lipopolysaccharide and Cyclic β-1,2-Glucans in Brucella-Mammalian Infections. | International journal of microbiology 20100101 |
| Characterization of the O-antigen in the lipopolysaccharide of Cronobacter (Enterobacter) malonaticus 3267. | Biochemistry and cell biology = Biochimie et biologie cellulaire 20091201 |
| Genetic analysis of the rkp-3 gene region in Sinorhizobium meliloti 41: rkpY directs capsular polysaccharide synthesis to KR5 antigen production. | Molecular plant-microbe interactions : MPMI 20091101 |
| Structure prediction and functional analysis of KdsD, an enzyme involved in lipopolysaccharide biosynthesis. | Biochemical and biophysical research communications 20091016 |
| Synthesis and antigenic properties of C-7-modified Kdo mono- and disaccharide ligands and Kdo disaccharide interresidue lactones. | Carbohydrate research 20090908 |
| WaaA of the hyperthermophilic bacterium Aquifex aeolicus is a monofunctional 3-deoxy-D-manno-oct-2-ulosonic acid transferase involved in lipopolysaccharide biosynthesis. | The Journal of biological chemistry 20090814 |
| Escherichia coli K-12 Suppressor-free Mutants Lacking Early Glycosyltransferases and Late Acyltransferases: minimal lipopolysaccharide structure and induction of envelope stress response. | The Journal of biological chemistry 20090605 |
| Profiles of structural heterogeneity in native lipooligosaccharides of Neisseria and cytokine induction. | Journal of lipid research 20090301 |
| The Kdo biosynthetic pathway toward OM biogenesis as target in antibacterial drug design and development. | Current drug discovery technologies 20090301 |
| Purification and characterization of the lipid A 1-phosphatase LpxE of Rhizobium leguminosarum. | The Journal of biological chemistry 20090102 |
| Identification of genes contributing to the virulence of Francisella tularensis SCHU S4 in a mouse intradermal infection model. | PloS one 20090101 |
| Klebsiella pneumoniae triggers a cytotoxic effect on airway epithelial cells. | BMC microbiology 20090101 |
| Structure of the oligosaccharide chain of the SR-type lipopolysaccharide of Ralstonia solanacearum Toudk-2. | Biomacromolecules 20080801 |
| The synthesis of the rhamnogalacturonan II component 3-deoxy-D-manno-2-octulosonic acid (Kdo) is required for pollen tube growth and elongation. | Journal of experimental botany 20080701 |
| Polysaccharides analysis of sinorhizobial capside by on-line anion exchange chromatography with pulsed amperometric detection and mass spectrometry coupling. | Journal of chromatography. A 20080328 |
| Exploration of specificity in germline monoclonal antibody recognition of a range of natural and synthetic epitopes. | Journal of molecular biology 20080321 |
| Single amino acid substitutions in either YhjD or MsbA confer viability to 3-deoxy-d-manno-oct-2-ulosonic acid-depleted Escherichia coli. | Molecular microbiology 20080201 |
| Innate immune responses of synthetic lipid A derivatives of Neisseria meningitidis. | Chemistry (Weinheim an der Bergstrasse, Germany) 20080101 |
| Genome biology of Actinobacillus pleuropneumoniae JL03, an isolate of serotype 3 prevalent in China. | PloS one 20080101 |
| Characterization of a waaF mutant of Helicobacter pylori strain 26695 provides evidence that an extended lipopolysaccharide structure has a limited role in the invasion of gastric cancer cells. | Biochemistry and cell biology = Biochimie et biologie cellulaire 20071001 |
| Human MD-2 discrimination of meningococcal lipid A structures and activation of TLR4. | Glycobiology 20070801 |
| Mesophilic Aeromonas UDP-glucose pyrophosphorylase (GalU) mutants show two types of lipopolysaccharide structures and reduced virulence. | Microbiology (Reading, England) 20070801 |
| The structure of the O-polysaccharide from the lipopolysaccharide of Providencia alcalifaciens O36 containing 3-deoxy-d-manno-oct-2-ulosonic acid. | Carbohydrate research 20070226 |
| Evaluation of thioglycosides of Kdo as glycosyl donors. | Carbohydrate research 20070226 |
| Engineering of a sialic acid synthesis pathway in transgenic plants by expression of bacterial Neu5Ac-synthesizing enzymes. | Plant biotechnology journal 20070101 |
| Overproduction and increased molecular weight account for the symbiotic activity of the rkpZ-modified K polysaccharide from Sinorhizobium meliloti Rm1021. | Glycobiology 20061201 |
| Structure of the Escherichia coli heptosyltransferase WaaC: binary complexes with ADP and ADP-2-deoxy-2-fluoro heptose. | Journal of molecular biology 20061020 |
| Yersinia pestis YrbH is a multifunctional protein required for both 3-deoxy-D-manno-oct-2-ulosonic acid biosynthesis and biofilm formation. | Molecular microbiology 20060801 |
| Structure of the lipid A-inner core region and biological activity of Plesiomonas shigelloides O54 (strain CNCTC 113/92) lipopolysaccharide. | Glycobiology 20060601 |
| Determination of endotoxin by the measurement of the acetylated methyl glycoside derivative of Kdo with gas-liquid chromatography-mass spectrometry. | Journal of microbiological methods 20060201 |
| Stereoselective synthesis of oligo-alpha(2,8)-3-deoxy-D-manno-2-octulosonic acid derivatives. | Angewandte Chemie (International ed. in English) 20060123 |
| Rhizobial exopolysaccharides: genetic control and symbiotic functions. | Microbial cell factories 20060101 |
| Brucella spp noncanonical LPS: structure, biosynthesis, and interaction with host immune system. | Microbial cell factories 20060101 |
| Spermicidal activity of bacterial lipopolysaccharide is only partly due to lipid A. | Journal of andrology 20060101 |
| The elicitation of plant innate immunity by lipooligosaccharide of Xanthomonas campestris. | The Journal of biological chemistry 20050930 |
| The linkage between O-specific caryan and core region in the lipopolysaccharide of Burkholderia caryophylli is furnished by a primer monosaccharide. | Carbohydrate research 20050815 |
| Purification and biochemical characterization of a pyruvate-specific class II aldolase, HpaI. | Biochemistry 20050712 |
| The complete structure of the core carbohydrate backbone from the LPS of marine halophilic bacterium Pseudoalteromonas carrageenovora type strain IAM 12662T. | Carbohydrate research 20050613 |
| Isolation and characterisation of the lipopolysaccharide from Acidiphilium strain GS18h/ATCC55963, a soil isolate of Indian copper mine. | FEMS microbiology letters 20050515 |
| Sinorhizobium meliloti strain 1021 produces a low-molecular-mass capsular polysaccharide that is a homopolymer of 3-deoxy-D-manno-oct-2-ulosonic acid harboring a phospholipid anchor. | Glycobiology 20050101 |
| Physicochemical characterization of carboxymethyl lipid A derivatives in relation to biological activity. | The FEBS journal 20050101 |
| New conditions for matrix-assisted laser desorption/ionization mass spectrometry of native bacterial R-type lipopolysaccharides. | Rapid communications in mass spectrometry : RCM 20050101 |
| Structure of the core oligosaccharide of a rough-type lipopolysaccharide of Pseudomonas syringae pv. phaseolicola. | European journal of biochemistry 20041201 |
| Structure of minor oligosaccharides from the lipopolysaccharide fraction from Pseudomonas stutzeri OX1. | Carbohydrate research 20041115 |
| The structure of the phosphorylated carbohydrate backbone of the lipopolysaccharide of the phytopathogen bacterium Pseudomonas tolaasii. | Carbohydrate research 20040913 |
| The complete structure of the lipooligosaccharide from the halophilic bacterium Pseudoalteromonas issachenkonii KMM 3549T. | Carbohydrate research 20040802 |
| Exopolysaccharides produced by Burkholderia cenocepacia recA lineages IIIA and IIIB. | Journal of cystic fibrosis : official journal of the European Cystic Fibrosis Society 20040801 |
| Biosynthesis of a novel 3-deoxy-D-manno-oct-2-ulosonic acid-containing outer core oligosaccharide in the lipopolysaccharide of Klebsiella pneumoniae. | The Journal of biological chemistry 20040702 |
| Structure and biological activity of the short-chain lipopolysaccharide from Bartonella henselae ATCC 49882T. | The Journal of biological chemistry 20040514 |
| Structural studies on the R-type lipopolysaccharide of Aeromonas hydrophila. | Carbohydrate research 20040315 |
| Structure of a highly phosphorylated lipopolysaccharide core in the Delta algC mutants derived from Pseudomonas aeruginosa wild-type strains PAO1 (serogroup O5) and PAC1R (serogroup O3). | Carbohydrate research 20031114 |
| Substitution pattern of 3-deoxy-D-manno-oct-2-ulosonic acid in bacterial lipopolysaccharides investigated by methylation analysis of whole LPS. | Carbohydrate research 20031114 |
| Structural characterization of the carbohydrate backbone of the lipopolysaccharide of Vibrio parahaemolyticus O-untypeable strain KX-V212 isolated from a patient. | Carbohydrate research 20031114 |
| Structural elucidation of a novel core oligosaccharide backbone of the lipopolysaccharide from the new bacterial species Agrobacterium larrymoorei. | Carbohydrate research 20031114 |
| Lipopolysaccharides of Vibrio cholerae. I. Physical and chemical characterization. | Biochimica et biophysica acta 20031015 |
| Structure of the lipopolysaccharide of Pseudomonas aeruginosa O-12 with a randomly O-acetylated core region. | Carbohydrate research 20030901 |
| Elucidation of the structure of the lipopolysaccharide core and the linkage between the core and the O-antigen in Pseudomonas aeruginosa immunotype 5 using strong alkaline degradation of the lipopolysaccharide. | Biochemistry. Biokhimiia 20030801 |
| Structural analysis of the carbohydrate backbone of Vibrio parahaemolyticus O2 lipopolysaccharides. | Carbohydrate research 20030501 |
| Structure of an acidic polysaccharide from the marine bacterium Pseudoalteromonas flavipulchra NCIMB 2033(T). | Carbohydrate research 20030214 |
| Structure-based design of novel inhibitors of 3-deoxy-D-manno-octulosonate 8-phosphate synthase. | Drug design and discovery 20030101 |
| Structural analyses of the lipopolysaccharides from Chlamydophila psittaci strain 6BC and Chlamydophila pneumoniae strain Kajaani 6. | Carbohydrate research 20011121 |
| Structural analysis of the exopolysaccharide from Burkholderia caribensis strain MWAP71. | Carbohydrate research 20010823 |
| The structure of the lipooligosaccharide (LOS) from the alpha-1,2-N-acetyl glucosamine transferase (rfaK(NMB)) mutant strain CMK1 of Neisseria meningitidis: implications for LOS inner core assembly and LOS-based vaccines. | Glycobiology 20010801 |
| Determination of the chemical structure of the capsular polysaccharide of strain B33, a fast-growing soya bean-nodulating bacterium isolated from an arid region of China. | The Biochemical journal 20010715 |
| Isolation and structural characterization of an R-form lipopolysaccharide from Yersinia enterocolitica serotype O:8. | European journal of biochemistry 20010201 |
| Aquifex aeolicus 3-deoxy-D-manno-2-octulosonic acid 8-phosphate synthase: a new class of KDO 8-P synthase? | Journal of molecular evolution 20010201 |
| X-ray diffraction and high-resolution NMR spectroscopic analysis of 2,4,7,8-tetra-O-acetyl-3-deoxy-alpha-D-manno-2-octulopyranosono-1,5-lactone. | Carbohydrate research 20010115 |
| Cloning, sequencing, and functional analysis of three glycosyltransferases involved in the biosynthesis of the inner core region of Klebsiella pneumoniae lipopolysaccharide. | Journal of endotoxin research 20010101 |
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