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Deoxy Sugars (4):
Recent article
Deoxy Sugars
Abstract
Biosynthetic genes encoding proteins involved in the first steps of deoxyhexose biosynthesis from D-glucose-1-phosphate were expressed in Saccharopolyspora erythraea. The resulting mutant was able to accumulate and utilise TDP-L-olivose. Co-expression of the spinosyn glycosyl transferase SpnP in the...
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PMID: 19343260
PDF is available here.
PDF is available here.
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Abstract
The cycloaddition reaction of acylketenes with vinyl ethers affords an extremely direct route to 2,6-dideoxysugars and their methyl ethers. The lithium enolate of commercial 2,6,6-trimethyldioxinone 3 was fluorinated in good yield to afford fluorinated dioxinone 8. An illustrative range of fluorinat...
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PMID: 19343243
PDF is available here.
PDF is available here.
Biochemistry (Washington) (48)12 2009
Abstract
3-Acetamido-3,6-dideoxy-alpha-D-glucose or Quip3NAc is an unusual dideoxy sugar found in the O-antigens of various Gram-negative bacteria and in the S-layer glycoprotein glycans of some Gram-positive bacteria. It is produced in these organisms as a dTDP-linked sugar, with five enzymes ultimately req...
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PMID: 19191736
PDF is available here.
PDF is available here.
Carbohydrate Research (344)2 2009
Abstract
Cyclic and linear oligosaccharides constituted with 2-deoxy sugar units are synthesized by an oligomerization reaction involving activated thioglycoside monomers, consisting of a 2-deoxy sugar unit. The oligomerization promoter plays an important role in the formation of either the cyclic- or the li...
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PMID: 19022421
PDF is available here.
PDF is available here.
Carbohydrate Research (343)18 2008
Abstract
A homogeneous sulfated heterorhamnan was obtained by aqueous extraction, then by ultrafiltration from the green seaweed Gayralia oxysperma. Besides alpha-L-rhamnose it contains glucuronic and galacturonic acids, xylose and glucose. The structure was established by methylation analyses of the carboxy...
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PMID: 18845298
PDF is available here.
PDF is available here.
Carbohydrate Research (343)18 2008
Abstract
An efficient synthesis of 4-methoxyphenyl alpha-L-Rhap-(1-->3)-alpha-L-Rhap-(1-->3)-alpha-L-Rhap-(1-->2)-6-deoxy-alpha-L-Talp, the tetrasaccharide related to the GPLs of Mycobacterium intracellare serotype 7, was achieved with 4-methoxyphenyl 3,4-di-O-benzoyl-6-deoxy-alpha-L-talopyranoside (6c) as t...
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PMID: 18954866
PDF is available here.
PDF is available here.
Journal of Biological Chemistry (283)48 2008
Abstract
We isolated different GPL species from M. avium, and using mass spectrometry and NMR analyses, characterized the molecular requirements of the GPL-TLR2 interaction. Interestingly, the extent of the respective acetylation and methylation of the 6-deoxytalose and rhamnose contained within the core GPL...
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PMID: 18824550
PDF is available here.
PDF is available here.
Carbohydrate Research (343)12 2008
Abstract
Our results highlight the capability of carbohydrates to act as scaffolds for the precise positioning of functional groups productive for a specific chemical reaction....
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PMID: 18062945
PDF is available here.
PDF is available here.
Carbohydrate Research (343)8 2008
Abstract
When 3-C-sulfonyl-pent-2-enofuranosides and 3-C-sulfonyl-hex-2-enofuranosides were reacted with primary and secondary amines, only the beta-anomeric methoxy group of the pent-2-enofuranoside did not cause any hindrance to incoming nitrogen nucleophiles. This resulted in the 'unusual' addition of ami...
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PMID: 18405888
PDF is available here.
PDF is available here.
Carbohydrate Research (343)6 2008
Abstract
We report here the chemical structure and the genetic locus of the CPS produced by C. jejuni strain CG8486, which belongs to the serotype HS:4 CPS complex. C. jejuni CG8486 CPS was observed to be composed of approximately 17 disaccharide repeating blocks of 4-substituted N-acetyl-beta-D-glucopyranos...
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PMID: 18346720
PDF is available here.
PDF is available here.
Journal of Bacteriology (190)10 2008
Abstract
Mycobacterium avium-Mycobacterium intracellulare complex (MAC) is the most common isolate of nontuberculous mycobacteria and causes pulmonary and extrapulmonary diseases. MAC species can be grouped into 31 serotypes by the epitopic oligosaccharide structure of the species-specific glycopeptidolipid...
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PMID: 18326570
PDF is available here.
PDF is available here.
Abstract
We describe the three-dimensional structure of the enzyme from Caulobacter crescentus determined to a nominal resolution of 1.8 A and refined to an R-factor of 17.9%. The overall fold of the enzyme places it into the well-characterized aspartate aminotransferase superfamily. Each subunit of the dime...
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PMID: 18247575
PDF is available here.
PDF is available here.
Carbohydrate Research (343)3 2008
Abstract
Two new ligands of transition metal cations based on galactose-derived scaffolds were synthesised: 1,5-anhydro-2-deoxy-3,4,6-tri-O-(2-picolyl)-D-galactitol and methyl 2-deoxy-3,4,6-tri-O-(2-picolyl)-alpha-D-galactopyranoside. These ligands permitted the isolation as single crystals of a Co(II) and a...
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PMID: 18179787
PDF is available here.
PDF is available here.
Carbohydrate Research (343)3 2008
Abstract
Synthesis of 2-deoxy-D-arabino/lyxo-hexopyranosyl disaccharides is reported. In these, the disaccharides contain 2-deoxy-arabino-hexopyranosyl and 2-deoxy-lyxo-hexopyranosyl sugars as either the reducing or the non-reducing or both the sugar units of the disaccharides. The activated 2-deoxy-1-thiogl...
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PMID: 18067881
PDF is available here.
PDF is available here.
Biochemical Journal (410)1 2008
Abstract
We focused on the elucidation of the biosynthesis pathway of dTDP-alpha-D-Quip3NAc (dTDP-3-acetamido-3,6-dideoxy-alpha-D-glucose) from the Gram-positive, anaerobic, thermophilic organism Thermoanaerobacterium thermosaccharolyticum E207-71, which carries Quip3NAc in its S-layer glycan. The biosynthes...
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PMID: 17941826
PDF is available here.
PDF is available here.
Organic Letters (10)2 2008
Abstract
ZACA-lipase-catalyzed acetylation tandem process has been shown to proceed satisfactorily with either TBS-protected 4-penten-1-ol or 3-buten-1-ol to provide the corresponding enantiomerically pure (R)-2-ethyl-1-alkanols. Either (R)-5 or (R)-6 was converted to 3 in seven steps. The other fragment 4 w...
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PMID: 18076181
PDF is available here.
PDF is available here.
Acta Biochimica Polonica (55)1 2008
Abstract
Mesorhizobium loti mutant 2213.1 derived from the wild-type strain NZP2213 by Tn5 mutagenesis showed impaired effectiveness of symbiosis with the host plant Lotus corniculatus (Turska-Szewczuk et al., 2007 Microbiol Res, in press). The inability of lipopolysaccharide (LPS) isolated from the mutant 2...
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PMID: 18217107
PDF is available here.
PDF is available here.
Carbohydrate Research (342)18 2007
Abstract
We report a comparison of several synthetic methodologies used to prepare protected derivatives of the 2,6-dideoxysugar l-digitoxose. A novel, stereoselective synthetic route to efficiently access methyl 4-O-tert-butyldimethylsilyl-2,6-dideoxy-3-O-trimethylsilyl-alpha-l-ribo-hexopyranoside in 35% yi...
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PMID: 17950714
PDF is available here.
PDF is available here.
Abstract
Significant progress has recently been made concerning the engineering of deoxysugar biosynthesis. The biosynthetic gene clusters of several deoxysugars from various polyketides and aminoglycosides-producing microorganisms have been cloned and studied. This review introduces the biosynthetic pathway...
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PMID: 18167436
PDF is available here.
PDF is available here.
Microbiology (153)Pt 12 2007
Abstract
I polyketide synthase involved in platenolide biosynthesis, 45 other genes have been identified. It was possible to propose a function for most of the inferred proteins in spiramycin biosynthesis, in its regulation, in resistance to the produced antibiotic or in the provision of extender units for t...
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PMID: 18048924
PDF is available here.
PDF is available here.
Journal of Bacteriology (189)23 2007
Abstract
We characterized the biosynthetic pathways for dTDP-d-Qui4N and dTDP-d-Qui4NAc (the nucleotide-activated precursors of d-Qui4NGlyAc and d-Qui4NAc in O antigens). Predicted genes involved in the synthesis of the two sugars were cloned, and the gene products were overexpressed and purified as His-tagg...
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PMID: 17905981
PDF is available here.
PDF is available here.
Abstract
We incubated hIAPP transgenic mouse islets for up to 7 days in 16.7 mM glucose (conditions that result in amyloid deposition) plus increasing concentrations of the inhibitor. WAS-406 at doses of 0, 10, 100, and 1,000 microM resulted in a dose-dependent decrease in amyloid deposition (% islet area oc...
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PMID: 17804609
PDF is available here.
PDF is available here.
Carbohydrate Research (342)14 2007
Abstract
The O-polysaccharide was isolated by mild acid degradation of the lipopolysaccharide of Providencia alcalifaciens O6 and studied by sugar and methylation analysis, selective hydrolytic removal of 3,6-dideoxy-L-xylo-hexose (colitose, Col), (1)H and (13)C NMR spectroscopy, including 2D (1)H,(1)H COSY,...
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PMID: 17559819
PDF is available here.
PDF is available here.
Carbohydrate Research (342)11 2007
Abstract
Over-expressed GerB (dTDP-4-keto-6-deoxy-d-glucose aminotransferase) of Streptomyces sp. GERI-155 was used in the enzymatic synthesis of dTDP-4-amino-4,6-dideoxy-D-glucose (2) from dTDP-4-keto-6-deoxy-D-glucose (1). [Carbohydrate structure: see text]. Five enzymes including dTMP kinase (TMK), acetat...
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PMID: 17532307
PDF is available here.
PDF is available here.
Biochemistry (Washington) (46)31 2007
Abstract
Desosamine is a 3-(dimethylamino)-3,4,6-trideoxyhexose found, for example, in such macrolide antibiotics as erthyromycin, azithromycin, and clarithromycin. The efficacies of these macrolide antibiotics are markedly reduced in the absence of desosamine. In the bacterium Streptomyces venezuelae, six e...
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PMID: 17630700
PDF is available here.
PDF is available here.
Carbohydrate Research (342)10 2007
Abstract
The synthesis of either anomers of aryl 2-deoxy-D-glycopyranosides from 2-deoxy-1-thioglycosides is reported. The alpha-anomers form as the major product when thioglycosides react with differently substituted phenols and naphthols, in the presence of N-iodosuccinimide/triflic acid. On the other hand...
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PMID: 17477910
PDF is available here.
PDF is available here.
Journal of Organic Chemistry (72)15 2007
Abstract
A chemoenzymatic synthesis of deoxy sugar esters is described. The synthesis is based on the O-alkylation of carboxylic acid with 2-bromo-5-acetoxypentanal. The method allows treatment of hydroxy carboxylic acids without protection of alcoholic hydroxyl groups. Several stereoisomeric deoxy sugar est...
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PMID: 17602527
PDF is available here.
PDF is available here.
Microbiology (153)Pt 7 2007
Abstract
The O-antigen moiety of the LPS is one of the most variable cell surface components of the Gram-negative bacterial outer membrane. Variation is due to the presence of different sugars and sugar linkages. Here, it is reported that a group of Escherichia coli O serogroups (O17, O44, O73, O77 and O106)...
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PMID: 17600060
PDF is available here.
PDF is available here.
Carbohydrate Research (342)9 2007
Abstract
3,4,6-Tri-O-acetyl-D-galactal, 3,4,6-tri-O-acetyl-D-glucal and 3,6,2',3',4'6'-hexa-O-acetyl-D-lactal were reacted with N-hydroxymethylphthalimide and boron trifluoride etherate to produce the corresponding phthalimidomethyl unsaturated glycosides via Ferrier rearrangement. When the galactal derivati...
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PMID: 17407773
PDF is available here.
PDF is available here.
Journal of Biological Chemistry (282)26 2007
Abstract
We describe the first three-dimensional structure of this sugar isomerase complexed with dTDP and solved to 1.5 A resolution. The FdtA dimer assumes an almost jellyfish-like appearance with the sole alpha-helices representing the tentacles. Formation of the FdtA dimer represents a classical example...
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PMID: 17459872
PDF is available here.
PDF is available here.
Journal of Molecular Biology (369)5 2007
Abstract
We describe the structure of a complex containing an inhibitory analogue of UDP-galactose, UDP-2F-galactose, in a complex with the Arg365Lys mutant of alpha3GT. The inhibitor is bound in a distorted, bent configuration and comparison with the structure of the apo form of this mutant shows that the i...
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PMID: 17493636
PDF is available here.
PDF is available here.
Carbohydrate Research (342)8 2007
Abstract
Armed deoxyhexose glycosyl donors are very reactive and sometimes too uncontrollably activated in glycosylation reactions; yields can be thereby reduced, especially when unreactive glycosyl acceptors are involved. In this paper, the behaviour of a range of deoxyhexose trihaloacetimidate (trichloro-...
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PMID: 17335788
PDF is available here.
PDF is available here.
Abstract
Carbohydrate Research (342)5 2007
Abstract
Carbohydrate-based vinyl selenides of the arabino, ribo and 2-deoxy-ribo configuration have been prepared by Wittig-type reactions of various protected furanoses. Moderate yields were always obtained due to the nature and reactivity of both carbohydrate lactols and selenium-based olefinating reagent...
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PMID: 17258697
PDF is available here.
PDF is available here.
Carbohydrate Research (342)3-4 2007
Abstract
An oligosaccharide that corresponds to the repeating unit of the O-polysaccharide was obtained by mild acid degradation of the lipopolysaccharide of Providencia alcalifaciens O36. Structural studies of the oligosaccharide and O-deacylated lipopolysaccharide were performed using sugar and methylation...
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PMID: 16815342
PDF is available here.
PDF is available here.
Journal of Bacteriology (189)3 2007
Abstract
We defined the complete structure of a novel serotype 7 GPL that has a unique terminal amido sugar. The main molecular mass is 1,874, and attached to the tetrapeptide-amino alcohol core is the serotype 7-specific oligosaccharide unit of 4-2'-hydroxypropanoyl-amido-4,6-dideoxy-2-O-methyl-beta-hexose-...
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PMID: 17122347
PDF is available here.
PDF is available here.
Carbohydrate Research (342)1 2007
Abstract
A glyconucleoside containing a thioglycoside linkage, namely 1-(3-S-beta-D-ribofuranosyl-2,3-dideoxy-3-thio-beta-D-ribofuranosyl)-thymine, has been prepared through condensation of a suitably protected derivative of 3'-thiothymidine with an activated ribose sugar. NMR has been used to study the conf...
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PMID: 17145047
PDF is available here.
PDF is available here.
Abstract
We propose here a method, based on deprotection of benzylated cyclodextrins, to selectively access a variety of complex structures with two or three new different functionalities on the primary platform. Our strategy is based on a mechanistic hypothesis involving the approach of an aluminium reagent...
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PMID: 18022890
PDF is available here.
PDF is available here.
Abstract
Mikrobiologiia (76)4 2007
Abstract
For the first time, from the surface of the dikaryotic mycelium of the xylotrophic basidiomycete Grifola frondosa 0917 a lectin has been isolated with a molecular mass of 68 +/- 1 kDa, consisting of two subunits of 33-34 kDa each. The lectin is a hydrophilic glycoprotein with the protein : glycan ra...
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PMID: 17974205
PDF is available here.
PDF is available here.
Abstract
The crystalline form of 1-deoxy-D-tagatose, C6H12O5, is shown to be 1-deoxy-alpha-D-tagatopyranose; the absolute configuration is determined by use of D-lyxono-1,4-lactone as the starting material. The title compound crystallized as concomitant polymorphs from a mixture of ethyl actate and methanol....
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PMID: 17206062
PDF is available here.
PDF is available here.
Glycobiology (16)12 2006
Abstract
The structure of the complex mixture of the core oligosaccharide components of the lipooligosaccharide (LOS) fraction of Agrobacterium tumefaciens strain TT111 was determined directly on the deacetylated products by means of spectroscopical methods. The rhamnan oligosaccharide elongating the inner K...
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PMID: 16877750
PDF is available here.
PDF is available here.
Abstract
The C-3 deoxygenation step in the biosynthesis of d-forosamine (4-N,N-dimethylamino-2,3,4,6-tetradeoxy-d-threo-hexopyranose), a constituent of spinosyn produced by Saccharopolyspora spinosa, was investigated. The spnQ gene, proposed to encode a TDP-4-keto-2,6-dideoxy-d-glucose 3-dehydratase was clon...
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PMID: 17076492
PDF is available here.
PDF is available here.
Abstract
Combinatorial biosynthesis was applied to Streptomyces deoxysugar biosynthesis genes in order to reconstitute "unnatural natural gene clusters" for the biosynthesis of four D-deoxysugars (D-olivose, D-oliose, D-digitoxose, and D-boivinose). Expression of these gene clusters in Streptomyces albus 16F...
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PMID: 17021216
PDF is available here.
PDF is available here.
Abstract
The formation of acetic acid was elucidated based on volatile reaction products and related nonvolatile key intermediates. The origin and yield of acetic acid were determined under well-controlled conditions (90-120 degrees C, pH 6-8). Experiments with various 13C-labeled glucose isotopomers in the...
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PMID: 16939325
PDF is available here.
PDF is available here.
Carbohydrate Research (341)11 2006
Abstract
A photoinduced electron-transfer (PET) reaction was used for the deoxygenation at C-2 of aldonolactones derivatized as 2-O-[3-(trifluoromethyl)benzoyl] or benzoyl esters. By irradiation of different D-galactono- and D-glucono-1,4-derivatives, with a 450W lamp, using 9-methylcarbazole as photosensiti...
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PMID: 16696960
PDF is available here.
PDF is available here.
Carbohydrate Research (341)10 2006
Abstract
Six (3,4,4',6',3'' or 6'')-monodeoxy analogues of the title trisaccharide (1-6) have been prepared utilising monodeoxy monosaccharide precursors. The reducing end deoxy derivatives were synthesised by N-iodosuccinimide/silver trifluoromethanesulfonate (NIS/AgOTf)-promoted couplings of a common disac...
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PMID: 16616903
PDF is available here.
PDF is available here.
Abstract
Recent development of a new class of patented alkylsaccharide transmucosal delivery enhancement agents, collectively designated as Intravail (Aegis Therapeutics) absorption enhancers, has created opportunities for new therapeutic options across a broad spectrum of human diseases. Int...
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PMID: 16822227
PDF is available here.
PDF is available here.
Abstract
Recent development of a new class of patented alkylsaccharide transmucosal delivery enhancement agents, collectively designated as Intravail (Aegis Therapeutics) absorption enhancers, has created opportunities for new therapeutic options across a broad spectrum of human diseases. Intravail absorptio...
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PMID: 16822227
PDF is available here.
PDF is available here.
Abstract
The synthesis of d- and l-glycero-alpha-manno-thioheptopyranosides, protected with 4,6-O-alkylidene-type acetals is described. In glycosylations carried out with preactivation with the 1-benzenesulfinylpiperidine/trifluoromethanesulfonic anhydride couple, both the D- and L-glycero series exhibit exc...
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PMID: 16771524
PDF is available here.
PDF is available here.
Journal of Bacteriology (188)10 2006
Abstract
We mutated a number of them and tested the ability of the mutants to nodulate a variety of legumes. At the same time, changes in the production of surface polysaccharides (particularly the rhamnan O antigen) were examined. Deletion of rmlB to wbgA and mutation in fixF abolished rhamnan synthesis. Mu...
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PMID: 16672619
PDF is available here.
PDF is available here.
Carbohydrate Research (341)4 2006
Abstract
Replacement of specific hydroxyl groups by fluorine in carbohydrates is an ongoing challenge from chemical, biological, and pharmaceutical points of view. A rapid and efficient two-step, regio- and stereoselective synthesis of 2-deoxy-2-(R)-fluoro-beta-d-allose (2-(R)-fluoro-2-deoxy-beta-d-allose; 2...
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PMID: 16413000
PDF is available here.
PDF is available here.
Abstract
Chromomycin A3 is an antitumor drug produced by Streptomyces griseus subsp. griseus. It consists of a tricyclic aglycone with two aliphatic side chains and two O-glycosidically linked saccharide chains, a disaccharide of 4-O-acetyl-D-oliose (sugar A) and 4-O-methyl-D-oliose (sugar B), and a trisacch...
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PMID: 16391039
PDF is available here.
PDF is available here.
FEMS Microbiology Letters (199)1 2006
Abstract
Smooth-type lipopolysaccharide (LPS) of Burkholderia pseudomallei has been reported to contain two kinds of O-antigenic polysaccharides, a 1,3-linked homopolymer of 6-deoxy-heptose and a polymer with a repeating unit of 21923)-glucose-(121923)-6-deoxy-talose-(12192 with O-acetyl or O-methyl modificat...
PDF is available here.
PDF is available here.
Journal of Organic Chemistry (70)25 2005
Abstract
[reaction: see text] A general procedure for the stereoselective synthesis of 2-deoxy-2-iodo-hexo- and -hepto-pyranosyl glycosides from furanoses is reported. The proposed methodology provides a new route for accessing 2-deoxy-oligosaccharides. The procedure involves three reactions: Wittig-Horner o...
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PMID: 16323838
PDF is available here.
PDF is available here.
Carbohydrate Research (340)17 2005
Abstract
Sunlight-mediated photooxygenation of 3-O-acetyl and 3-O-methyl derivatives of 1,2-O-alkylidene-5(E)-eno-5,6,8-trideoxy-alpha-D-xylo-oct-1,4-furano-7-uloses (1a-e) in carbon tetrachloride solution gave stable 4,7-epidioxy derivatives in 4R (2a-e) and 4S (3a-e) configurations. The presence of an endo...
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PMID: 16182263
PDF is available here.
PDF is available here.
Carbohydrate Research (340)16 2005
Abstract
Hexopyranoside methyl alpha-D-mannoside (8) was homologated to yield 7-(acylamino)-2,6,7-trideoxy-heptopyranosides 19-26. A crucial reaction step is the radical cleavage of benzylidene derivative 10 to obtain bromide 11. Since nucleophilic substitution of 11 with KCN provided the bicyclic nitrile 13...
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PMID: 16168970
PDF is available here.
PDF is available here.
Carbohydrate Research (340)16 2005
Abstract
Both cis- and trans-2-substituted-1,2,3,6-tetrahydro-pyridin-3-ols have been prepared via an aldol condensation-ring-closing metathesis sequence. A stereodivergent synthesis of optionally functionalized deoxyimino sugars was achieved via asymmetric dihydroxylation or epoxidation/nucleophilic substit...
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PMID: 16169539
PDF is available here.
PDF is available here.
Molecular Microbiology (58)1 2005
Abstract
The indolocarbazole staurosporine is a potent inhibitor of a variety of protein kinases. It contains a sugar moiety attached through C-N linkages to both indole nitrogen atoms of the indolocarbazole core. Staurosporine biosynthesis was reconstituted in vivo in a heterologous host Streptomyces albus b...
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PMID: 16164546
PDF is available here.
PDF is available here.
Journal of Organic Chemistry (70)20 2005
Abstract
In the synthesis of vinyl sulfone-modified hex-5-enofuranosides, the E/Z ratios of the products are influenced by the stereoelectronic property of a group present at the C-3 position. This observation has been utilized to influence the diastereoselectivity of addition of amines to C-5 of vinyl sulfo...
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PMID: 16277326
PDF is available here.
PDF is available here.