Synthesis of allyl O-[sodium (α-d-glcero-d-talo-2-octulopyranosyl)onate]-(2 → 6)-2-acetamido-2-deoxy-β-d-glucopyranoside, a core constituent of the lipopolysaccharide from Acinetobacter calcoaceticus NCTC 10305

Gass, Josef; Strobl, Martina; Loibner, Andreas P.; Kosma, Paul; Zähringer, Ulrich

doi:10.1016/0008-6215(93)80005-y

Cited by 44 publications

(8 citation statements)

References 22 publications

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“…The low field shifts of the protons at A2 and A3 compared with free NH 2 (12) were indicative of N-acylation at these positions. A ␤-linkage was assigned to the anomeric proton at ␦4.35 because of its relatively smallagreed with that of synthetic ␣-Ko derivatives (15). These findings indicated that sugar E was ␣-Ko.…”

Section: Thementioning

confidence: 86%

Characterization of a Novel d-Glycero-d-talo-oct-2-ulosonic acid-substituted Lipid A Moiety in the Lipopolysaccharide Produced by the Acetic Acid Bacterium Acetobacter pasteurianus NBRC 3283

Hashimoto

Ozono

Furuyashiki

et al. 2016

Journal of Biological Chemistry

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Acetobacter pasteurianus is an aerobic Gram-negative rod that is used in the fermentation process used to produce the traditional Japanese black rice vinegar kurozu. Previously, we found that a hydrophobic fraction derived from kurozu stimulates Toll-like receptors to produce cytokines. LPSs, particularly LPS from A. pasteurianus, are strong candidates for the immunostimulatory component of kurozu. The LPS of A. pasteurianus remains stable in acidic conditions during the 2 years of the abovementioned fermentation process. Thus, we hypothesized that its stability results from its structure. In this study, we isolated the LPS produced by A. pasteurianus NBRC 3283 bacterial cells and characterized the structure of its lipid A component. The lipid A moiety was obtained by standard weak acid hydrolysis of the LPS. However, the hydrolysis was incomplete because a certain proportion of the LPS contained acid-stable D-glycero-D-talo-oct-2-ulosonic acid (Ko) residues instead of the acid-labile 3-deoxy-D-manno-oct-2-ulosonic acid residues that are normally found in typical LPS. Even so, we obtained a Ko-substituted lipid A with a novel sugar backbone, ␣-Man(1-4)[␣-Ko(2-6)]␤-GlcN3N(1-6)␣-GlcN(1-1)␣-GlcA. Its reducing end GlcN(1-1)GlcA bond was also found to be quite acid-stable. Six fatty acids were attached to the backbone. Both the whole LPS and the lipid A moiety induced TNF-␣ production in murine cells via Toll-like receptor 4, although their activity was weaker than those of Escherichia coli LPS and lipid A. These results suggest that the structurally atypical A. pasteurianus lipid A found in this study remains stable and, hence, retains its immunostimulatory activity during acetic acid fermentation.

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Section: Thementioning

confidence: 86%

Characterization of a Novel d-Glycero-d-talo-oct-2-ulosonic acid-substituted Lipid A Moiety in the Lipopolysaccharide Produced by the Acetic Acid Bacterium Acetobacter pasteurianus NBRC 3283

Hashimoto

Ozono

Furuyashiki

et al. 2016

Journal of Biological Chemistry

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“…Either the Kdo that links the core region to lipid A (KdoI, in Acinetobacter) [20][21][22] or the branching Kdo attached to it (KdoII, in Burkholderia cepacia and Yersinia pestis) [23][24][25][26][27][28][29] may be replaced by the stereochemically similar sugar, dglycero-d-talo-oct-2-ulopyranosonic acid (Ko). [30] This sugar was also detected in the LPSs of B. caryophylli; however, its location could not be determined. [31] The biosynthesis of Ko and the regulation of the exchange between Kdo and Ko have not been elucidated so far.…”

Section: Introductionmentioning

confidence: 95%

Lipopolysaccharides from Serratia marcescens Possess One or Two 4‐Amino‐4‐deoxy‐L‐arabinopyranose 1‐Phosphate Residues in the Lipid A and D‐glycero‐D‐talo‐Oct‐2‐ulopyranosonic Acid in the Inner Core Region

Vinogradov¹,

Lindner²,

Seltmann³

et al. 2006

Chemistry A European J

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The carbohydrate backbones of the core-lipid A region were characterized from the lipopolysaccharides (LPSs) of Serratia marcescens strains 111R (a rough mutant strain of serotype O29) and IFO 3735 (a smooth strain not serologically characterized but possessing the O-chain structure of serotype O19). The LPSs were degraded either by mild hydrazinolysis (de-O-acylation) and hot 4 M KOH (de-N-acylation), or by hydrolysis in 2 % aqueous acetic acid, or by deamination. Oligosaccharide phosphates were isolated by high-performance anion-exchange chromatography. Through the use of compositional analysis, electrospray ionization Fourier transform mass spectrometry, and 1H and 13C NMR spectroscopy applying various one- and two-dimensional experiments, we identified the structures of the carbohydrate backbones that contained D-glycero-D-talo-oct-2-ulopyranosonic acid and 4-amino-4-deoxy-L-arabinose 1-phosphate residues. We also identified some truncated structures for both strains. All sugars were D-configured pyranoses and alpha-linked, except where stated otherwise.

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“…However, we found that the coupling of 4 with acetobromoglucose at room temperature (rt) in the presence of 2,4-lutidine (1.5 equiv), gave orthoester 9 as crystals in quantitative yield. Me 3 SiOTf-catalyzed rearrangement [9] of 9 selectively offered the 1,6-linked trisaccharide 11 (76%), and acetylation gave 13. To confirm the selectivity of the rearrangement, 9 was acetylated first, then isomerized with TMSOTf to produce a compound (74%) identical to 13 [10].…”

Section: Resultsmentioning

confidence: 99%

“…After completion of the reaction, the mixture was partitioned between CH 2 Cl 2 (40 mL) and H 2 O (40 mL) and the organic phase was washed with 10% aq Na 2 S 2 O 3 (20 mL) and aq NaCl (30 mL) and concentrated under reduced pressure. The residual oil was purified by column chromatography with 1:1 petro- 3,4, (9).-As described in the preparation of 8, the coupling of compound 4 (1.0 g, 1.9 mmol) with 'acetobromoglucose' (0.94 g, 2.3 mmol) was carried out in the presence of silver triflate (590 mg, 2.3 mmol) and lutidine (265 mL, 2.3 mmol) to furnish 9 (R,S) (1.58 g, 96%) as an amorphous solid. Further purification by HPLC (1:1 petroleum ether-EtOAc) gave the R and S isomers as crystals.…”

Section: -O-mentioning

confidence: 99%

A highly convergent and effective synthesis of the phytoalexin elicitor hexasaccharide

Wang

Kong

1999

Carbohydrate Research

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Synthesis of allyl O-[sodium (α-d-glcero-d-talo-2-octulopyranosyl)onate]-(2 → 6)-2-acetamido-2-deoxy-β-d-glucopyranoside, a core constituent of the lipopolysaccharide from Acinetobacter calcoaceticus NCTC 10305

Cited by 44 publications

References 22 publications

Characterization of a Novel d-Glycero-d-talo-oct-2-ulosonic acid-substituted Lipid A Moiety in the Lipopolysaccharide Produced by the Acetic Acid Bacterium Acetobacter pasteurianus NBRC 3283

Characterization of a Novel d-Glycero-d-talo-oct-2-ulosonic acid-substituted Lipid A Moiety in the Lipopolysaccharide Produced by the Acetic Acid Bacterium Acetobacter pasteurianus NBRC 3283

Lipopolysaccharides from Serratia marcescens Possess One or Two 4‐Amino‐4‐deoxy‐L‐arabinopyranose 1‐Phosphate Residues in the Lipid A and D‐glycero‐D‐talo‐Oct‐2‐ulopyranosonic Acid in the Inner Core Region

A highly convergent and effective synthesis of the phytoalexin elicitor hexasaccharide

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