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1. (Article ID: 9852)
 
Takahashi N, Hotta T, Ishihara H, Mori M, Tejima S, Bligny R, Akazawa T, Endo S, Arata Y
Xylose-containing common structural unit in N-linked oligosaccharides of laccase from sycamore cells
Biochemistry 25(2) (1986) 388-395
 

The structures of asparagine-linked oligosaccharides of laccase excreted by sycamore (Acer pseudoplatanus L.) cells are reported. Peptic glycopeptides obtained from the laccase were treated with N-oligosaccharide glycopeptidase (EC 3.5.1.52) to release the oligosaccharide moieties. The oligosaccharides thus obtained were fractionated into six components by gel filtration, thin-layer chromatography, and high-performance liquid chromatography. The structures of the isolated oligosaccharides were determined by sugar analysis, exoglycosidase digestion, and methylation analysis in combination with high-resolution proton nuclear magnetic resonance spectroscopy. It was found that (1) the six oligosaccharides are a series of compounds of xylose-containing biantennary complex types that share as the core a common structural unit, i.e., Xyl-β(l-2)[Man-α(l-6)]Man-β(l-4)GlcNAc-β(l-4)[Fuc-α(1-3)]GlcNAc, and (2) mannose, N-acetylglucosamine, galactose, and fucose residues are additionally linked to the core as the outer chain moieties.

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2. (Article ID: 10005)
 
York WS, Oates JE, van Halbeek H, Darvill AG, Albersheim P, Tiller PR, Dell A
Location of the O-acetyl substituents on a nonasaccharide repeating unit of sycamore extracellular xyloglucan
Carbohydrate Research 173 (1988) 113-132
 

The locations of the O-acetyl substituents on the major nonasaccharide repeating unit of the xyloglucan isolated from sycamore extracellular polysaccharides were determined by a combination of analytical methods, including f.a.b.-m.s. and 1H-n.m.r. spectroscopy. The O-2-linked-β-D-galactosyl residue of the nonasaccharide was found to be the dominant site of O-acetyl substitution. Both mono-O-acetylated and di-O-acetylated β-D-galactosyl residues were detected. The degree of O-acetylation of the β-D-galactosyl residue, was estimated by 1H-n.m.r. spectroscopy to be 55-60% at O-6, 15-20% at O-4, and 20-25% at O-3. 1H-n.m.r. spectroscopy also indicated that approximately 50% of the β-D-galactosyl residues are mono-O-acetylated, 25-30% are di-O-acetylated, and 20% are not acetylated.

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3. (Article ID: 10073)
 
Stevenson TT, Darvill AG, Albersheim P
Structure of plant cell walls XXIII. Structural features of the plant cell-wall polysaccharide rhamnogalacturonan-II
Carbohydrate Research 182 (1988) 207-226
 

Rhamnogalacturonan-II (RG-II), isolated from the cell walls of suspension-cultured sycamore cells, has been further characterized. End-group analysis of RG-II showed that the polysaccharide contains about 30 glycosyl residues. Some 28 residues have been found as constituents of well characterized oligosaccharide fragments of RG-II. RG-II was treated with lithium metal dissolved in ethylenediamine to degrade the glycosyluronic acid residues. The major product was isolated, characterized, and shown to be the triglycosylalditol α-Xyl-(1→3)-α-Fuc-(1→4)-β-Rha-(1→31)-apiitol. This tetrasaccharide fragment of RG-II has three residues in common with a previously characterized heptasaccharide that had been derived from RG-II by partial hydrolysis with acid. RG-II was found to contain a large number of branched galactosyluronic acid residues that have not yet been identified as components of oligosaccharide fragments, although they are undoubtedly part of an octa(galactosyluronic acid) fragment generated by partial acid hydrolysis. The results of sequential partial acid hydrolysis provided evidence that, in RG-II, the extremely acid-labile 3-deoxy-d-manno-2-octulosonic-acid and 3-deoxy-d-lyxo-2-heptulosaric acid residues are attached to O-3 of 3,4-linked galactosyluronic acid residues, and that the mildly acid-labile apiofuranosyl residues are attached to O-2 of 2,4-linked galactosyluronic acid residues. These and previously published data suggested that RG-II has a highly branched structure, arranged around an α-(1→4)-linked galactosyluronic acid backbone.

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4. (Article ID: 10195)
 
Kiefer LL, York WS, Albersheim P, Darvill AG
Structure of plant cell walls. XXX. Structural characterization of an arabinose-containing heptadecasaccharide enzymically isolated from sycamore extracellular xyloglucan
Carbohydrate Research 197 (1990) 139-158
 

An arabinose-containing heptadecasaccharide, generated by endoglucanase digestion of the xyloglucan secreted by suspension-cultured sycamore cells, was structurally characterized. The structure of the heptadecasaccharide was unambiguously determined through combined data generated by 1H-n.m.r. spectroscopic, fast-atom bombardment mass spectrometric, and glycosyl-composition and glycosyl-linkage analyses of the intact heptadecasaccharide and of oligosaccharide fragments of the heptadecasaccharide. 1D and 2D 1H-n.m.r. analyses provided data for assignment of the anomeric configurations of the glycosidic linkages, as well as information about the glycosylic and linkage compositions of the heptadecasaccharide. F.a.b.-m.s. data provided the molecular weight and supplied critical information about the glycosylic composition and glycosylic sequence of the heptadecasaccharide. The heptadecasaccharide was found to be a combination of previously characterized nona- and hepta-saccharide components of xyloglucan. The nonasaccharide was shown to be glycosidically linked to the heptasaccharide through C-4 and the β-glucosyl residue nearest to the nonreducing end of the heptasaccharide component. An arabinosyl residue was glycosidically linked at C-2 of the same β-glucosyl residue at the non-reducing end of the heptasaccharide component of the heptadecasaccharide. Although the presence of arabinosyl residues in sycamore xyloglucan has been recognized since 1973, the location of the arabinosyl residues had not been ascertained.

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5. (Article ID: 10203)
 
Hisamatsu M, York WS, Darvill AG, Albersheim P
The structure of plant cell walls. XXXV. Characterization of seven xyloglucan oligosaccharides containing from seventeen to twenty glycosyl residues
Carbohydrate Research 227 (1992) 45-71
 

The complete primary structures of seven oligosaccharide subunits of the xyloglucan secreted by suspension-cultured acer pseudoplatanus cells were determined. The oligosaccharides, ranging in size from 17 to 20 glycosyl residues, were generated by treatment of the xyloglucan with an endo-β-(1→4)-glucanase. The oligosaccharide components of a fraction obtained by Bio-Gel P-2 chromatography of enzyme-treated xyloglucan were further purified by normal-phase h.p.l.c. and then converted to the corresponding oligoglycosyl alditols by reduction with NaBH4. The oligoglycosyl alditols, are purification to near homogeneity by reversed-phase h.p.l.c., were structurally characterized by 1H-n.m.r. spectroscopy, fast-atom bombardment mass spectrometry (f.a.b-m.s.), and analysis of their glycosyl-residue and glycosyl-linkage compositions. Novel structural elements of xyloglucans were observed in this study, including β-d-xylopyranosyl and α-l-arabinofuranosyl-(1→3)-β-d-xylopyranosyl sidechains. The results also extend our list of correlations between 1H-n.m.r. resonances and specific structural features of xyloglucans and thus enhance our ability to determine the structures of xyloglucans from various sources.

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6. (Article ID: 10227)
 
Tezuka K, Hayashi M, Ishihara H, Akazawa T, Takahashi N
Studies on synthetic pathway of xylose-containing N-linked oligosaccharides deduced from substrate specificities of the processing enzymes in sycamore cells (Acer pseudoplatanus L.)
European Journal of Biochemistry 203 (1992) 401-413
 

We measured the activities of α-1,3-mannosyl-glycoprotein β-1,2-N-acetylglucosaminyltransferase, α-1,6-mannosyl-glycoprotein β-1,2-N-acetylglucosaminyltransferase, β-1,4-mannosyl-glycoprotein β-1,2-xylosyltransferase and glycoprotein 3-α-L-fucosyltransferase in the Golgi fraction of suspension-cultured cells of sycamore (Acer pseudoplatanus L.) using fluorescence-labelled oligosaccharides as acceptor substrates for these transferase reactions. The structures of the pyridylaminated oligosaccharides produced by these reactions were analyzed by two-dimensional sugar mapping using high-performance liquid chromatography. We demonstrated that (formula; see text) was processed to produce by these in vitro reactions. On the basis of these results, we discuss a biosynthetic pathway for xylose containing N-linked oligosaccharides in plant glycoproteins.

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7. (Article ID: 10292)
 
Kiefer LL, York WS, Darvill AG, Albersheim P
Structure of plant cell walls. Part 27. Xyloglucan isolated from suspension-cultured sycamore cell walls is O-acetylated
Phytochemistry 28 (1989) 2105-2107
 

Xyloglucan oligosaccharides were enzymically released from purified cell walls isolated from suspension-cultured sycamore cells. The O-acetyl substitution pattern of these oligosaccharides was determined by 1H NMR spectroscopy. This analysis revealed that most of the 2-linked galactosyl residues of the decasaccharide and nonasaccharide fragments of cell wall xyloglucan are O-acetyl substituted, while the heptasaccharide fragment does not contain O-acetyl substituents. This acetylation pattern does not differ significantly from that of the same xyloglucan oligosaccharides enzymically released from the xyloglucan secreted by suspension-cultured sycamore cells.

cell wall, 1H NMR, xyloglucan, O-acetate

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8. (Article ID: 10340)
 
Stevenson TT, Darvill AG, Albersheim P
Structure of plant cell walls XXII. 3-Deoxy-D-lyxo-2-heptulosaric acid, a component of the plant cell-wall polysaccharide rhamnogalacturonan-II
Carbohydrate Research 179 (1988) 269-288
 

3-Deoxy-d-lyxo-heptulosaric acid (DHA) has been identified as a component of plant cell walls. This sugar was found in the pectic polysaccharide rhmanogalacturonan-II as a component of the disaccharide β-l-Araf-(1→5)-d-DHAp. The structural formula and linkage position of DHA were determined by mass spectrometry of several derivatives. The lyxo configuration was determined by 1H-n.m.r. spectroscopy of a derivative of the isolated disaccharide. The d configuration was determined by partial degradation of DHA to l-glyceric acid. DHA was found to be present in the primary cell walls of many higher plants, including several dicots, two monocots, and a gymnosperm, but was not detected in two bacterial lipopolysaccharides.

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9. (Article ID: 10341)
 
Stevenson T, Darvill AG, Albersheim P
Structure of plant cell walls XXIII. Structural features of the plant cell-wall polysaccharide rhamnogalacturonan-II
Carbohydrate Research 199 (1988) 269-288
 

3-Deoxy-d-lyxo-heptulosaric acid (DHA) has been identified as a component of plant cell walls. This sugar was found in the pectic polysaccharide rhmanogalacturonan-II as a component of the disaccharide β-l-Araf-(1→5)-d-DHAp. The structural formula and linkage position of DHA were determined by mass spectrometry of several derivatives. The lyxo configuration was determined by 1H-n.m.r. spectroscopy of a derivative of the isolated disaccharide. The d configuration was determined by partial degradation of DHA to l-glyceric acid. DHA was found to be present in the primary cell walls of many higher plants, including several dicots, two monocots, and a gymnosperm, but was not detected in two bacterial lipopolysaccharides.

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10. (Article ID: 10373)
 
Lau JM, McNeil M, Darvill AG, Albersheim P
Treatment of rhamnogalacturonan I with lithium in ethylenediamine
Carbohydrate Research 168 (1987) 245-274
 

Rhamnogalacturonan I is a pectic polysaccharide that is solubilized from the walls of suspension-cultured sycamore cells (Acer pseudoplatanus) by the action of a highly purified endo-1,4-α-polygalacturonanase. Rhamnogalacturonan I has a linear backbone consisting of the diglycosyl repeating unit, →4)-α-d-GalpA-(1→2)-α-l-Rhap-(1→. Approximately half of the α-l-rhamnosyl residues of the backbone are branched at O-4. Selective cleavage at the galactosyluronic acid residues of the backbone by treatment of rhamnogalacturonan I wit lithium in ethylenediamine resulted in the release of the neutral glycosyl-residue sidechains that had been attached to the backbone. Various analytical techniques, including combined liquid chromatography-mass spectrometry, combined gas-liquid chromatography-mass spectrometry, and 1H-nuclear magnetic resonance spectroscopy, were used to determine the structure of the side chains. The majority of the sidechains were isolated as oligoglycosylalditols, with rhamnitol at the “reducing” end. Terminal 2-, 4-, or 6-linked galactosyl residues were found attached to O-4 of the rhamnitol residues The 2-, 4-, and 6-linked galactosyl residues had terminal or 2-linked