Synthesis of a model, linear d-mannopentaose for the nonreducing-end sequence of the cell-surface d-mannan of Escherichia coli, Candida albicans, and Saccharomyces cerevisiae

Ogawa, Tomoya; Yamamoto, Hisao

doi:10.1016/0008-6215(85)85150-8

Cited by 43 publications

(8 citation statements)

References 29 publications

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“…The O-antigen structure of O9 LPS has been studied using methylation analysis, smith degradation, optical rotation and enzymatic methods, [9][10][11] however, a precise assignment by NMR spectroscopy has not been conducted.…”

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confidence: 99%

An Unambiguous Assignment and Structural Analysis Using Solution NMR Experiments of O-Antigen from Escherichia coli ATCC23505 (Serotype O9)

et al. 2007

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Bacterial lipopolysaccharides (LPSs) are major surfaceexposed structural components of the outer membrane of Gram-negative bacteria. LPSs consist of lipid A, a core region, and an O-antigen region in many bacteria.1) LPSs play an important role in the pathogenicity of Gram-negative infections. In experimental animals, purified LPSs induce numerous pathophysiological activities that can lead to shock and death, a condition called "Sepsis".2) Most of these biological activities, including the induction of inflammatory cytokines, are expressed by the lipid A moiety, a ubiquitous component of LPSs that is structurally similar and serologically cross-reacting among Enterobacteriaceae, via toll-like receptor 4 (TLR4). [3][4][5] However, numerous recent studies have revealed that LPSs possessing the mannose homopolymer (MHP) as the O-antigen region, such as the LPS from Escherichia coli (E. coli) O9 (O9 LPS), exhibit several characteristic immunological activities differ from those of the well-known endotoxic shock. In addition, we previously described that the mannan moieties of Candida albicans water-soluble fraction, CAWS, from fungi shows similar immunological properties to Gramnegative bacterial O9 LPS.6) These characteristic activities should be exhibited by recognizing mannose residues via lectins, such as mannose-binding lectin (MBL). 7,8) Therefore, analyzing the structure of O-antigens, especially mannoserich regions, is important for understanding some of the biological activities of LPSs.The O-antigen structure of O9 LPS has been studied using methylation analysis, smith degradation, optical rotation and enzymatic methods, [9][10][11] however, a precise assignment by NMR spectroscopy has not been conducted.In general, focusing on the anomeric proton as the starting point for assignment, TOCSY and HSQC-TOCSY experiments are useful for the analysis of individual sugar components in polysaccharides.12) However, in some cases, the assignment can be empirically based due to signals that heavily overlap and small J coupling constants. For the reasons mentioned above, we attempted to apply recently developed pulse sequences, the heteronuclear 2-bond correlation (H2BC) experiments [13][14][15] in order to achieve an unambiguous assignment of the high mannose type polysaccharide, the O-antigen from O9 LPS.In the present study, we report on the structure of the Oantigen of O9 LPS, and completely assign all protons and carbons using 1D-, 2D-NMR spectroscopy including the DQF-COSY, TOCSY, NOESY, HSQC, H2BC, HSQC-TOCSY, and HMBC methods. ExperimentalBacterial Strain and Conditions for Growth E. coli ATCC23505 was obtained from American Type Culture Collection (ATCC). The strain was grown in Luria Bertani (LB) medium.Preparation of LPS O9 LPS was extracted from E. coli ATCC23505 (O9:K9B:H12) by the phenol water method.16) The acetone-dried cells (10 g) cultured in LB medium were suspended in 175 ml of distilled water (preheated at 65°C), and then 175 ml of 90% liquid phenol (preheated at 65°C) was added under vigorous st...

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An Unambiguous Assignment and Structural Analysis Using Solution NMR Experiments of O-Antigen from Escherichia coli ATCC23505 (Serotype O9)

et al. 2007

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“…Nevertheless, disaccharide 12α was easily separated from the reaction mixture. Removal of the allyl group was carried out in one step using palladium chloride in acetic acid-water [28] and gave 13 in 74% yield. Phosphorylation using the phosphoroamidite method [29] gave 14, which after hydrogenolysis yielded the desired compound III.…”

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confidence: 99%

A New Preparative Synthesis of 1-D-6-O-(2-Amino-2-Deoxy-D-glycopyranosyl)-chiro-Inositol 1-Phosphate and 1,2-Cyclic Phosphate

Martín‐Lomas¹,

Flores-Mosquera

Khiar

2000

Eur. J. Org. Chem.

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A convenient preparative synthesis of 1‐D‐6‐O‐(2‐amino‐2‐deoxy‐α‐D‐glycopyranosyl)‐chiro‐inositol 1‐phosphate (III) and ‐1,2‐cyclic phosphate (IV) using D‐chiro‐inositol as starting material is reported. Compound III has been previously found to behave as type P inositolphosphoglycans (the putative second messengers of insulin‐like growth factor I) in organotypic cultures of chicken embryo. The synthesis of III and IV, now reported, considerably improves previous synthesis of III and permits the effective preparation of these substances for biological investigation.

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“…Deallylation of 3 with PdCl 2 in methanol, 9 followed by trichloroacetimidate formation 10 with trichloroacetonitrile in the presence of DBU, produced the disaccharide donor 5 (67% for two steps). Coupling…”

Section: Resultsmentioning

confidence: 99%

A concise synthesis of two isomeric pentasaccharides, the O repeat units from the lipopolysaccharides of P. syringae pv. porri NCPPB 3364T and NCPPB 3365

Zhang

Kong

2004

Carbohydrate Research

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, the O repeats from the lipopolysaccharides of Pseudonomonas syringae pv. porri NCPPB 3364 T and 3365 was achieved via assembly of the building blocks, allyl 3, (7), and allyl 2,4-di-O-benzoyl-a-L L -rhamnopyranoside (10). Coupling of 1 with 2 followed by deallylation and trichloroacetimidate formation gave the disaccharide donor 5, while condensation of 6 with 7, followed by dechloroacetylation, offered the disaccharide acceptor 9. Then, 5 was coupled with 10 to obtain the trisaccharide 11, and subsequent deallylation and trichloroacetimidate formation furnished the trisaccharide donor 13. Coupling of 9 with 13, followed by deprotection, afforded pentasaccharide 19, while condensation of 9 with 5, followed by deallylation and trichloroacetimidate formation, gave the tetrasaccharide donor 16, whose coupling with 10 and subsequent deprotection yielded another pentasaccharide 22.

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Synthesis of a model, linear d-mannopentaose for the nonreducing-end sequence of the cell-surface d-mannan of Escherichia coli, Candida albicans, and Saccharomyces cerevisiae

Cited by 43 publications

References 29 publications

An Unambiguous Assignment and Structural Analysis Using Solution NMR Experiments of O-Antigen from Escherichia coli ATCC23505 (Serotype O9)

An Unambiguous Assignment and Structural Analysis Using Solution NMR Experiments of O-Antigen from Escherichia coli ATCC23505 (Serotype O9)

A New Preparative Synthesis of 1-D-6-O-(2-Amino-2-Deoxy-D-glycopyranosyl)-chiro-Inositol 1-Phosphate and 1,2-Cyclic Phosphate

A concise synthesis of two isomeric pentasaccharides, the O repeat units from the lipopolysaccharides of P. syringae pv. porri NCPPB 3364T and NCPPB 3365

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