2-Deoxyglucose selectively inhibits Fc and complement receptor-mediated phagocytosis in mouse peritoneal macrophages II. Dissociation of the inhibitory effects of 2-deoxyglucose on phagocytosis and ATP generation. (1/352)
Macrophages incubated in 2-deoxy-D-glucose (2-dG)-containing medium showed a marked decrease in cellular ATP content, and were unable to ingest IgG- and complement-coated erythrocytes via the corresponding membrane receptors for these ligands. However, the inhibitory effects of 2-dG on Fc- and C3 receptor-mediated phagocytosis were not a consequence of lowered macrophage ATP levels since addition of glucose or mannose to the culture medium restored the capacity of the macrophages to ingest IgG- and C3-coated particles without increasing ATP levels. These results indicate that Fc- and C3 receptor-mediated phagocytosis (opsonin dependent) differs qualitatively from the ingestion of latex and zymosan particles (opsonin independent); they suggest that the same regulatory molecules govern the responses of phagocytic cells to signals initiated by both the Fc and C3 receptors. The possibility that these molecules are regulated by glycosylation is discussed. (+info)Structure of the O-specific polysaccharide of a serologically separate strain Proteus penneri 2 from a new proposed serogroup O66. (2/352)
O-specific polysaccharide chain of Proteus penneri strain 2 lipopolysaccharide was studied by full and partial acid hydrolysis, Smith degradation, methylation analysis, and NMR spectroscopy, including two-dimensional rotating-frame NOE spectroscopy (ROESY) and 1H,13C heteronuclear multiple-quantum coherence (HMQC) experiments. Together with D-glucose and 2-acetamido-2-deoxy-D-glucose, the polysaccharide was found to contain two rarely occurring sugars, 6-deoxy-L-talose (L-6dTal) and 2,3-diacetamido-2,3,6-trideoxy-L-mannose (L-RhaNAc3NAc), and the following structure of a non-stoichiometrically O-acetylated tetrasaccharide repeating unit was established: [equation: see text] The O-specific polysaccharide studied has a unique composition and structure and, accordingly, P. penneri 2 is serologically separate among Proteus strains. Therefore, we propose for P. penneri 2 a new Proteus O-serogroup O66 where this strain is at present the single representative. (+info)Interactions on 3-deoxy and 6-deoxy derivatives of N-acetyl-D-glucosamine with hen lysozyme. (3/352)
The interactions of deoxy derivatives of GlcNAc, 6-deoxy-GlcNAc, and 3-deoxy-GlcNAc with hen egg-white lysozyme [EC 3.2.1.17] were studied at various pH's by measuring the changes in the circular dichroic (CD) band at 295 nm. It was shown that 6-deoxy-GlcNAc and 3-deoxy-GlcNAc bind at subsite C of lysozyme and compete with GlcNAc. The pH dependence of the binding constant of 6-deoxy-GlcNAc was the same as that of GlcNAc. On the other hand, the binding constants of 3-deoxy-GlcNAc were 3--10 times smaller than those of GlcNAc in the pH range from 3 to 9. X-ray crystallographic studies show that O(6) and O(3) of GlcNAc at subsite C are hydrogen-bonded to the indole NH's of Trp 62 and Trp 63, respectively, but the above results indicate that Trp 63, not Trp 62, is important for the interaction of GlcNAc with lysozyme. (+info)2-Deoxyglucose selectively inhibits Fc and complement receptor-mediated phagocytosis in mouse peritoneal macrophages. I. Description of the inhibitory effect. (4/352)
Incubation of normal or thioglycollate-elicited mouse peritoneal macrophages with 2-deoxy-D-glucose (2-dG) inhibits the capacity of these macrophages to phagocytize IgG- or complement-coated particles via their Fc and C3 receptors. 2-dG has no inhibitory effect on the capacity of these macrophages to phagocytize latex or zymosan particles, which are ingested in the absence of specific opsonins, and it does not inhibit binding of IgG- or C3-coated particles to their respective receptors on the macrophage's plasma membrane. 2-dG exerts its inhibitory effect on the macrophage and not on the opsonized particle. The inhibition is independent of particle size, occurs within 15-30 min of addition of this glucose analogue to the medium at 37 degrees C, cannot be overcome by supra-agglutinating amounts of opsonizing antibody, and is completely reversible by substitution of 5.5 mM glucose for 50 mM 2-dG in the medium. Addition of equimolar amounts of glucose or mannose, but not of fructose, galactose, fucose, or glucosamine, to medium containing 50 mM 2-dG results in substantial reversal of the inhibitory effect of 2-dG on Fc and C3 receptor mediated phagocytosis. (+info)Interference of nucleoside diphosphate derivatives of 2-deoxy-D-glucose with the glycosylation of virus-specific glycoproteins in vivo. (5/352)
The predominant effect of 2-deoxy-D-glucose on chick embryo cells infected with Semliki Forest virus is an interference with glycosylation of virus-specific glycoproteins; this results in a block of synthesis of infectious virus. Incorporation of radioactive mannose is blocked severely in the presence of 2-deoxyglucose in the cultural medium although it is readily phosphorylated and subsequently activated by GTP to yield GDP-mannose, which accumulates under these conditions. The intracellular concentrations of GDP-mannose and UDP-N-acetyl-D-hexosamine are not reduced in the presence of the inhibitor. An equimolar concentration of mannose in the cultural medium competes with the inhibitory effect of the deoxysugar and drops the cellular pool of GDP-2-deoxy-D-glucose below the level of detection, at the same time restoring the synthesis of infectious virus. When the intracellular concentration of UDP-2-deoxyglucose is reduced by addition of glucose into the cultural medium the inhibition of virus synthesis by the deoxysugar and the concentration of GDP-2-deoxyglucose within the cells remain near to the values when the inhibitor is present alone. It is concluded that among the metabolites of 2-deoxyglucose which occur in vivo after addition of 2-deoxyglucose to the culture medium, GDP-2-deoxyglucose is the agent responsible for inhibition of glycosylation of viral glycoproteins. (+info)[18F]-labeled 3-deoxy-3-fluoro-D-glucose: synthesis and preliminary biodistribution data. (6/352)
A cyclotron target system for the production of anhydrous [18F] fluoride ion has been developed and used for the synthesis of carrier-free [18F]-3-deoxy-3fluoro-D-glucose (3-FDG). The synthesis is sufficiently rapid and efficient to allow production of usable amounts of 3-FDG with a 6-MeV cyclotron. Preliminary animal studies show that 3-FDG is in fact a glucose analog. (+info)The effect of 2-deoxy-D-glucose and D-glucose on the efferent discharge rate of sympathetic nerves. (7/352)
Efferent discharges were recorded from nerve filaments dissected from the adrenal and renal nerves in the rabbit. 2. An increase in discharge rate was observed in the adrenal nerve filaments following I.V. administration of 2-deoxy-D-glucose (2-DG). No change in discharge rate after 2-DG infusion was observed in the renal nerve filaments. 3. A decrease in discharge rate of the adrenal nerve filaments was observed after I.V. injection of glucose, but there was no change in the activity of renal nerve filaments. 4. Transection of the spinal cord abolished the adrenal nerve response to the systemic administration of 2-DG and glucose. 5. It is suggested that there might be a pathway from the hypothalmic area to the adrenal nerve cells of the spinal cord, but not to the renal nerve cells, through which activity of the adrenal nerve might be changed in response to 2-DG and glucose infusion. (+info)Thymidine diphosphate-6-deoxy-L-lyxo-4-hexulose reductase synthesizing dTDP-6-deoxy-L-talose from Actinobacillus actinomycetemcomitans. (8/352)
The serotype c-specific polysaccharide antigen of Actinobacillus actinomycetemcomitans NCTC 9710 contains an unusual sugar, 6-deoxy-L-talose, which has been identified as a constituent of cell wall components in some bacteria. Two genes coding for thymidine diphosphate (dTDP)-6-deoxy-L-lyxo-4-hexulose reductases were identified in the gene cluster required for biosynthesis of serotype c-specific polysaccharide. Both dTDP-6-deoxy-L-lyxo-4-hexulose reductases were overproduced and purified from Escherichia coli transformed with the plasmids containing these genes. The sugar nucleotides converted by both reductases were purified by reversed-phase high performance liquid chromatography and identified by (1)H nuclear magnetic resonance and gas-liquid chromatography. The results indicated that one of two reductases produced dTDP-6-deoxy-L-talose and the other produced dTDP-L-rhamnose (dTDP-6-deoxy-L-mannose). The amino acid sequence of the dTDP-6-deoxy-L-lyxo-4-hexulose reductase forming dTDP-6-deoxy-L-talose shared only weak homology with that forming dTDP-L-rhamnose, despite the fact that these two enzymes catalyze the reduction of the same substrate and the products are determined by the stereospecificity of the reductase activity. Neither the gene for dTDP-6-deoxy-L-talose biosynthesis nor its corresponding protein product has been found in other bacteria; this biosynthetic pathway is identified here for the first time. (+info)Deoxy sugars, also known as deoxyriboses, are sugars that have one or more hydroxyl (-OH) groups replaced by a hydrogen atom. The most well-known deoxy sugar is deoxyribose, which is a component of DNA (deoxyribonucleic acid).
Deoxyribose is a pentose sugar, meaning it has five carbon atoms, and it differs from the related sugar ribose by having a hydrogen atom instead of a hydroxyl group at the 2' position. This structural difference affects the ability of DNA to form double-stranded helices through hydrogen bonding between complementary base pairs, which is critical for the storage and replication of genetic information.
Other deoxy sugars may also be important in biology, such as L-deoxyribose, a component of certain antibiotics, and various deoxyhexoses, which are found in some natural products and bacterial polysaccharides.
Deoxy sugar
DTDP-glucose 4,6-dehydratase
DTDP-4-dehydrorhamnose 3,5-epimerase
DTDP-6-deoxy-L-talose 4-dehydrogenase
Rhamnose
Fuculose
Quercitrin
Propylene glycol
Fucose
Thymidine diphosphate glucose
Desosamine
Daunosamine
Digitalose
CM chondrite
Ferrier rearrangement
Cyclopropenium ion
David M. Lemal
Synthesis of nucleosides
Cladinose
Microbial metabolism
Sulfoglycolysis
Dideoxynucleotide
Deoxyribose
Fluorodeoxyglycosylamine
Glycoazodyes
Sulfoquinovose
Macrolide
2-NBDG
2-Deoxy-D-glucose
Oleandrose
Deoxy sugar - Wikipedia
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Ribose12
- Deoxyribose is derived from the same precursor as ribose being that the reduction of the sugar with the extra hydroxyl group results in the deoxy-sugar, which has its hydroxyl group replaced with a hydrogen atom. (wikipedia.org)
- The CAS register number of 2-Deoxy-D-ribose is 533-67-5. (lookchem.com)
- Uses of 2-Deoxy-D-ribose: it can be used to produce lithium 2-deoxy-D-erythro-pentonate at temperature of 40 °C. This reaction will need reagent 3 M KOH, 30 percent H 2 O 2 , MgO, 0.1 M LiOH with reaction time of 18 hours. (lookchem.com)
- The result produced a variety of simple sugars - including ribose, a key component of RNA. (cosmosmagazine.com)
- RNA is made from monomers of the sugar β-D-ribose and the sugar along with the nitrogenous base and inorganic phosphate is called a ribonucleotide - without the phosphate, it's a nucleoside. (herbs2000.com)
- DNA is made of monomers formed by the pentose sugar deoxy-ribose, along with a nitrogenous base and inorganic phosphate to make a deoxyribonucleotide. (herbs2000.com)
- The DNA monomers are differentiated from the RNA monomers by the absence of an oxygen at the number two carbon in the sugars and are called a 2-deoxy-β-D-ribose sugars. (herbs2000.com)
- Horton Derek, Kokrady Satish S.: Acyclic-sugar nucleoside analogs derived from cytosine with the d-aldopentoses, and from uracil with d-lyxose and d-ribose. (iupac.org)
- The sugar in DNA has 5 carbon atoms (labelled 1′ - 5′), and is called deoxy-ribose (hence the "Deoxy-ribo" in DNA). (tourwimberleytx.com)
- The deoxy prefix indicates that the 2′ carbon atom of the sugar lacks the oxygen atom that is linked to the 2′ carbon atom of ribose (the sugar in ribonucleic acid, or RNA), as shown in Figure 5.2. (tourwimberleytx.com)
- The pentose sugar in DNA is called deoxyribose, and in RNA, the sugar is ribose. (tourwimberleytx.com)
- The difference between the sugars is the presence of the hydroxyl group on the 2′ carbon of the ribose and its absence on the 2′ carbon of the deoxyribose. (tourwimberleytx.com)
Hydroxyl group2
- Deoxy sugars are sugars that have had a hydroxyl group replaced with a hydrogen atom. (wikipedia.org)
- Reversibly catalyzes the oxidation of a hydroxyl group of sugar alcohols to form a keto sugar, aldehyde or lactone. (reference.md)
Glycosides7
- Definition Glycosides are non-reducing organic compounds that on hydrolysis with acids or enzymes yield: 1- A sugar part (or glycone, formed of one or more sugar units). (slideshare.net)
- These constitute the non-sugar moieties of the glycosides Types acc. (slideshare.net)
- to glycosidic linkage: They contain free -OH group (in O-glycosides), free NH (in N-glycosides), free SH(in S- glycosides) The common linkage between the sugar part and the aglycone is an oxygen linkage connecting the reducing group of a sugar and an alcoholic or a phenolic hydroxyl group of the aglycone to give O-glycosides. (slideshare.net)
- to the stereo of the sugars: sugars exist in isomeric - and -forms, both - and -glycosides are theoretically possible, but most of the naturally occurring glycosides are of the -type Types acc. (slideshare.net)
- Glycosides Dr. Mostafa Hegazy The sugar moiety in glycosides consists of either : 1- A monosaccharide molecule (e.g. glucose, rhamnose. (slideshare.net)
- Common sugar in glycosides is -D-glucose, Other sugars (like pentoses and deoxy-hexoses) Sugar derivatives (e.g. uronic acids such as glucuronic acid in glycyrrhizin) are also found. (slideshare.net)
- Glycosides Dr. Mostafa Hegazy Sugar Attachment The sugar moiety is attached to the aglycone part mostly at : one position (e.g. in monodesmosidic saponins), or two different positions (e.g. in bidesmosidic saponins). (slideshare.net)
Pentose sugar1
- a pentose sugar C 5 H 10 O 4 that is a structural element of DNA. (tourwimberleytx.com)
Derivatives4
- In a paper published in the journal Nature Communications , Michel Nuevo, George Cooper, and Scott Sandford, all from NASA's Ames Research Centre in the US, report detecting 2-deoxyribose - the sugar component of DNA - and several deoxysugar derivatives in residues produced from the ultraviolet irradiation of ice mixtures under standard astrophysical conditions in the laboratory. (cosmosmagazine.com)
- The presence of sugar derivatives in primitive meteorites, together with other compounds of biological interest such as amino acids, nucleobases, and amphiphiles is consistent with a scenario in which a significant fraction of the inventory of compounds from which biological processes started on the primitive Earth may have been delivered via comets, meteorites, and interplanetary dust particles (IDPs)," the authors write. (cosmosmagazine.com)
- Blieszner Kathleen C., Horton Derek, Markovs Robert A.: Acyclic-sugar purine nucleosides derived from d-glucose: stereochemical correlations in acyclic-sugar derivatives unequally substituted at c-1. (iupac.org)
- Baker David C., Horton Derek: Synthesis and stereochemical characterization of a series of five-carbon, acyclic-sugar derivatives of 1,6-dihydro-6-thioxopurine (6-mercaptopurine). (iupac.org)
Nucleosides1
- Horton Derek, Liu Charng-Ming: Microbial oxidation as a route for cyclization of acylic-sugar nucleosides. (iupac.org)
Mannose1
- Acid hydrolysis of DOM polysaccharides releases a suite of characteristic neutral sugars (glucose, galactose, mannose, rhamnose, fucose and xylose), but most of the polysaccharide (80-90%) resists hydrolysis and undergoes Maillard-like reactions between amino- and reducing sugars. (copernicus.org)
Phosphate1
- The addition of the phosphate group also covalently connected to the sugar unit completes the basic component of the nucleic acid polymer. (herbs2000.com)
Residues1
- The unique LPS structure and associated sugar residues and arrangement are outlined in Figure 2 . (europeanpharmaceuticalreview.com)
Covalently1
- These components of the nucleic acids are linked together covalently through a glycosidic bond formed between the sugar unit and the nitrogenous base. (herbs2000.com)
Acid4
- Unique sugars in LPS include the core sugar, KDO (3 deoxy-α-D-manno-octulosonic acid), and unique arrangements of sugars in the O-antigen moiety, which are used to distinguish bacterial strains when characterising various gram-negative bacteria foodborne illness outbreaks (serotyping). (europeanpharmaceuticalreview.com)
- containing less oxygen in the molecule than the compound from which it is derived deoxy sugars -usually used in combination deoxyribonucleic acid. (tourwimberleytx.com)
- The sugar present in the DNA is 2'deoxyribose, a five carbon monosaccharide, which is devoid of oxygen in its 2′ position, hence the name deoxyribonucleic acid. (tourwimberleytx.com)
- The sugar in deoxyribonucleic acid (DNA) is deoxyribose. (tourwimberleytx.com)
Polysaccharides1
- However, a novel class of polysaccharides characterized by high N-acetyl aminosugar and 6-deoxysugar content, escapes rapid degradation and accumulates as a constituent of marine dissolved organic matter (DOM). (copernicus.org)
Glucose1
- CDP-D-Glucose is the precursor for synthesizing four of the five naturally occurring 3,6-dideoxy sugars-abequose (3,6-dideoxy-D-Xylo-hexose), ascarylose (3,6-dideoxy-L-arabino-hexose), paratose (3,6-dideoxy-D-ribohexose), and tyvelose (3,6-dideoxy-D-arabino-hexose. (nih.gov)
Amino5
- They are the amino sugar part and the hexose ring in the center, which can be 2-deoxystreptamine or streptidine. (pharmacygyan.com)
- In this antibiotic contains two or more amino sugars joined in glycoside linkage and a centrally located substituted 1,3-diaminocyclo hexane (aminocyclitol) loop. (pharmacygyan.com)
- Two amino sugars are bound to strepidine in streptomycine . (pharmacygyan.com)
- Two amino sugars are bound to 2-deoxy strepamine in the kanamycin and gentamycin families. (pharmacygyan.com)
- Amino sugars are bound to 2-deoxy streptamine in the neomycin family. (pharmacygyan.com)
Atoms1
- Some biologically important dideoxy sugars, sugars that have had two hydroxyl groups replaced with hydrogen atoms, include colitose and abequose. (wikipedia.org)
Pathway1
- The sugar blocks an enzyme of the so-called shikimate pathway, a metabolism route that only occurs in microorganisms and plants. (rural21.com)
Bacteria2
- The rare deoxy sugar was isolated from cultures of the freshwater cyano-bacterium Synechococcus elongatus , which is capable of inhibiting the growth of related bacteria strains. (rural21.com)
- has been identified as the 2nd most consensus (ERIC) sequences which · 60 environmental samples were tak- frequent organism causing ventilator- are common to Gram-negative enteric en throughout the ICU, including associated pneumonia, the 4th most bacteria [11,12]. (who.int)
Inhibit1
- Deoxy-ATP (dATP) can reach toxic levels that inhibit ribonucleotide reductase, an enzyme essential for synthesis of DNA precursors. (medscape.com)
Synthesis2
Hydrolysis2
- To circumvent this, we modified our hydrolysis conditions to promote sugar-sugar cleavage. (copernicus.org)
- After hydrolysis the sugar part has reducing characters. (slideshare.net)
Five-carbon1
- deoxyribose, also called d-2-deoxyribose, five-carbon sugar component of DNA (q.v. (tourwimberleytx.com)
Experiments1
- Laboratory experiments have shown that a sugar critical to the structure of DNA arises when ice formed on planets, asteroids and meteorites is subjected to ultraviolet radiation. (cosmosmagazine.com)
Molecule3
- Scientists at the University of Tübingen in Germany have discovered a sugar molecule that inhibits plants and microorganisms and is harmless to human cells. (rural21.com)
- The newly discovered sugar molecule originating from cyanobacteria inhibits the growth of various microorganisms and plants, but is harmless to humans and animals. (rural21.com)
- The Tübingen research team consisting of chemists and microbiologists have now hit upon a very unusual antimetabolite with an incredibly simple chemical structure: a sugar molecule going by the scientific name of "7-desoxy-Sedoheptulose" (7dSh). (rural21.com)
Carbon2
- The term "deoxy" refers to the fact that there is no oxygen attached to the 2′ carbon atom . (tourwimberleytx.com)
- Is deoxyribose a 5 carbon sugar? (tourwimberleytx.com)
Microbial1
- Deoxysugars are ubiquitous in nature where they function in a variety of biological processes, including cell adhesion, immune response, determination of ABO blood groups, fertilization, antibiotic function, and microbial pathogenicity. (nih.gov)
Chemical1
- It also can be called as 2-Deoxy-D-erythropentose and the IUPAC name about this chemical is 3,4,5-trihydroxypentanal. (lookchem.com)
Deoxyribose1
- What is meant by the syllable deoxy in deoxyribose? (tourwimberleytx.com)
Core1
- The oligosaccharidic core consists of 10 - 12 sugars divided in a proximal and a distal region. (scirp.org)
Formation1
- The work continues about 25 years of experimentation regarding the formation of sugars as a result of non-biological astrophysical processes. (cosmosmagazine.com)
Presence1
- They also tested samples from selected meteorites and detected the presence of deoxysugars. (cosmosmagazine.com)
Means1
- Deoxy-Deus-in Latin means God! (tourwimberleytx.com)
Types1
- En Égypte, les isolats des patients étaient de types ERIC VII, VIII et IX et correspondaient à ceux des tubulures des appareils d'aspiration et de respiration artificielle et des cuvettes. (who.int)
Conversion1
- Bell R.Hays, Horton Derek, Williams Diana M., Winter-Mihaly Eva: Photochemical conversion of sugar dimethylthio-carbamates into deoxy sugars. (iupac.org)
Highly1
- Weidmann, H. Highly selective metal-graphite-induced reductions of deoxy halo sugars. (mpg.de)
Protein1
- Because the cross-links occurred between sulphur-rich parts of the mucin protein, the team developed a sulphur-containing anti-oxidant sugar called TDG (methyl 6-thio-6-deoxy-alpha-D-galactopyranoside) to reverse the effect. (thenakedscientists.com)
Group1
- In these processes, a tricoordinate boronic ester initially serves as a protective group for a sugar-derived 1,2- or 1,3-diol motif, permitting functionalization of free OH groups. (acs.org)