A Study of 13CH Coupling Constants in Pentopyranoses and Some of their Derivatives.

Bock, Klaus; Pedersen, Christian; Rasmussen, Poul; Jensen, R. B.; Dahl, Otto; Buchardt, Ole; Schroll, G.

doi:10.3891/acta.chem.scand.29b-0258

Cited by 218 publications

(53 citation statements)

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“…This was confirmed by the large values J C-1Ј,H-1Ј 170.5 Hz and 172.4 Hz, respectively, for BbGL-II and BbGL-II-Ac 4 (Table 3), which fall within the range expected for ␣ anomers (19), and observed for Me-␣-D-Galp (Table 3).…”

Section: Resultssupporting

confidence: 67%

“…This was confirmed by measurement of the values 1 J C-1Ј,H-1Ј 158.7 Hz and 157.4 Hz for BbGL-I and BbGL-I-Ac 3 , respectively (Table 3), which fall within the appropriate range for the ␤ anomeric configuration (19), as exemplified by the value 1 J C-1Ј,H-1 160.6 Hz observed for Me-␤-D-Galp (Table 3). The assignments of sugar ring size for BbGL-I and BbGL-I-Ac 3 were made on the basis of the similarity of the J values of the sugar rings to those of Me-␤-D-Galp (Table 3).…”

Section: Resultssupporting

confidence: 57%

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A newly discovered cholesteryl galactoside from Borrelia burgdorferi

Ben-Menachem

Kübler-Kiełb²,

Coxon³

et al. 2003

Proc. Natl. Acad. Sci. U.S.A.

148

128

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Two major glycolipids, which comprise Ϸ36% of the total lipid mass from Borrelia burgdorferi, the etiological agent of Lyme disease, were investigated. We determined the fatty acid type, sugar identity, anomeric configuration, and substituent type and position. The structures were identified as cholesteryl 6-O-acyl-␤-D-galactopyranoside (B. burgdorferi glycolipid 1, BbGL-I), and 1,2-di-O-acyl-3-O-␣-D-galactopyranosyl-sn-glycerol (BbGL-II). The major fatty acids were palmitate and oleate. The structures were corroborated by gas-liquid chromatography MS, matrix-assisted laser desorption͞ionization time-of-flight spectroscopy, fast atom bombardment MS, detailed NMR spectrometry, and metabolic labeling. This is a previously undescribed demonstration of a cholesteryl galactoside in bacteria. Lipopolysaccharide was not detected in B. burgdorferi. The two glycolipids have several properties suggesting they may function as lipopolysaccharide: both are main components of the bacterial membrane, surface exposed, and have a three-domain structure. BbGL-I elicited specific antibodies in mice and rabbits, and BbGL-II elicited antibodies that reacted with both glycolipids.T he etiological agent of Lyme disease, Borrelia burgdorferi, is transmitted to humans through the bite of Ixodes ticks. Lyme disease is a multisystem infection, which affects the skin, joints, nervous system, and heart (1). The licensed vaccine (LYMErix, SmithKline Beecham) contains recombinant lipidated OspA. Although lipopolysaccharide (LPS) has been identified in several spirochaetales, such as Leptospira (2) and Treponema (3), there is no evidence for the presence of LPS in Borrelia species (4).Two surface-exposed glycolipids identified in B. burgdorferi react with sera from Lyme disease patients (5-7). These immunoreactive glycolipids have been characterized as monogalactosyl diacylglycerolipids (8). It has been proposed that these glycolipids differ only in their fatty acid composition. We designated these glycolipids as B. burgdorferi glycolipid I (BbGL-I) and B. burgdorferi glycolipid II (BbGL-II). We show that although BbGL-II is a monogalactosyl diacylglycerol as reported (8), BbGL-I has the unique structure cholesteryl 6-O-acyl-␤-D-galactopyranoside. Experimental ProceduresOrganism and Growth Conditions. B. burgdorferi strains B31 (ATCC 35210), BL303 (courtesy of G. Wormser, Division of Infectious Diseases, New York Medical College, Valhalla) and N40 (courtesy of L. Bockenstedt, Department of Internal Medicine, Yale University School of Medicine, New Haven, CT) were cultivated in BSK-H medium (Sigma). Media were inoculated with 2% (vol͞vol) of a frozen culture and incubated statically at 37°C for 72 h to the mid-exponential growth phase. Cells were harvested by centrifugation at 12,000 ϫ g for 30 min, washed three times with cold PBS, and stored at Ϫ20°C.Lipid Extraction and Purification. Lipids were extracted from washed cells as described (9). The chloroform was removed, and the dried lipids (0.1-0.2 mg͞mg cell) dissolved in 1-2 ml of chlorofor...

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Section: Resultssupporting

confidence: 67%

Section: Resultssupporting

confidence: 57%

A newly discovered cholesteryl galactoside from Borrelia burgdorferi

Ben-Menachem

Kübler-Kiełb²,

Coxon³

et al. 2003

Proc. Natl. Acad. Sci. U.S.A.

148

128

View full text Add to dashboard Cite

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“…The assignment of signals in spectra of 0-specific polysaccharides was achieved by a comparison of spectral data for the polysaccharides with those for methyl-6-deoxyaltrosides (Table 3). A coupling constant ( J 13C1-H1 = 164 Hz) indicated P-configuration of the glycosidic linkage [18]. This conclusion is confirmed by the absence of signals in the field of 66 -68 ppm which are peculiar for C5 atoms of a-anomers [19].…”

Section: Nmr Spectroscopic Studiessupporting

confidence: 57%

Structural studies on O-specific polysaccharides of lipopolysaccharides from Yersinia enterocolitica serovars O:1,2a,3, O:2a,2b,3 and O:3

et al. 1985

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Lipopolysaccharides from Yersinia enterocolitica serovars 0 : 1,2a,3, 0: 2a,2b,3 and 0: 3 have been isolated and characterized. 6-Deoxy-~-altrose residues were shown to be the main constituents of lipopolysaccharides isolated in addition to residues of L-rhamnose, D-glucose, D-galactose, 2-acetamido-2-deoxy-~-glucose, 2-acetamido-2-deoxy-~-galactose, D-glycero-D-manno-heptose and L-glycero-D-manno-heptose, 3-deoxy-~-manno-octulosonic acid being minor components of sugar chains.

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“…Another study reported that peracetylated methyl b-d-ribopyranoside had at 70 % the 1 C 4 conformation, whereas its a-anomer corresponded to a 1:1 mixture of the chair forms, again based on 1 H NMR spectroscopy. [33] In our case we presume a near 1:1 equilibrium ( Figure 2) for compounds 17 and 18 (and probably their precursor 15), and for their resulting pyrophosphates 36 and 37 (see Scheme 9 below), as can be deduced from the proton coupling constants J H1,H2 (Table 1). Because both chair forms of the a-anomer are expected to give a small coupling constant, we were not able to determine which is the preferred conformation of compounds 19 and 20, but one may assume that the 4 C 1 form dominates, analogously to acylated derivatives.…”

Section: Synthesis Of Pentopyranose Tetrakisphosphatesmentioning

confidence: 99%

Polyphosphates and Pyrophosphates of Pentopyranoses and Pentofuranoses as Allosteric Effectors of Human Hemoglobin: Synthesis, Molecular Recognition, and Oxygen Release

et al. 2011

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Perphosphorylated pentopyranoses and pentofuranoses were synthesized from parent carbohydrates as potential allosteric effectors of hemoglobin (Hb). The construction of seven- and eight-membered cyclic pyrophosphates was also carried out successfully on most of the pentoses. All final compounds were tested for their efficiency on oxygen release from human Hb. Most proved to be efficient allosteric effectors, some of them with an affinity toward Hb and an effect on oxygen release from Hb approaching that of myo-inositol hexakisphosphate, which is one of the most active allosteric effectors of Hb. The efficacy was higher for free phosphates than for pyrophosphates.

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A Study of 13CH Coupling Constants in Pentopyranoses and Some of their Derivatives.

Cited by 218 publications

References 0 publications

A newly discovered cholesteryl galactoside from Borrelia burgdorferi

A newly discovered cholesteryl galactoside from Borrelia burgdorferi

Structural studies on O-specific polysaccharides of lipopolysaccharides from Yersinia enterocolitica serovars O:1,2a,3, O:2a,2b,3 and O:3

Polyphosphates and Pyrophosphates of Pentopyranoses and Pentofuranoses as Allosteric Effectors of Human Hemoglobin: Synthesis, Molecular Recognition, and Oxygen Release

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