The Structure of Pentasaccharides and Hexasaccharides from Blood Group Substance H

Kochetkov, N. K.; Derevitskaya, V. A.; Arbatsky, Nikolay P.

doi:10.1111/j.1432-1033.1976.tb10641.x

Cited by 50 publications

(23 citation statements)

References 11 publications

(1 reference statement)

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“…Thus the basal disaccharide being terminated with a-L-fucose residue at C-2 or a-N-acetylglucosamine residue at C-4 leads to trisaccharides described earlier [3]. On the other hand substitution of the basal disaccharide with disaccharide Gal(l-4)GlcNAc at C-6 of N-acetylgalactosaminitol residue leads after addition of two terminal monosaccharides to hexasaccharides [4]. The basal disaccharide bearing the disaccharide units at C-3 and C-6 of the galactose residue is the common structural element of series I oligosaccharides and that bearing disaccharide units at C-3 of galactose and C-6 of N-acetylgalactosaminitol residues is the common element of series I11 oligosaccharide structures.…”

Section: Discussionmentioning

confidence: 99%

“…%-Configuration of fucose residues in blood-group substances has been determined earlier [15] and especially proved for penta and hexasaccharides described in our previous paper [4]. 8-Galactosidase has completely split terminal galactose residues from oligosaccharides and their fragments and the respective degradation products were formed with a high yield; this has proved unambiguously the P-configuration of galactose residues.…”

Section: The Structure Of Oligosaccharidesmentioning

confidence: 95%

“…It is not surprising that attachment of an a-L-fucose residue stops the chain growth, since the sequence E-L-FUC( 1 + 2)P-~-Gal( 1 -i4)P-~-GlcNAc, constituting the complete determinant of blood-group H activity, appears. In all three cases of an a-N-acetylglucosamine residue occurring [3,4] it occupies the definite position, namely at C-4 of the galactose residue in the basal disaccharide (Fig. 7) and perhaps this position is the only possible site where it appears and stops further chain elongation.…”

Section: Discussionmentioning

confidence: 99%

“…Earlier we have reported the structure of trisaccharides [3], penta and hexasaccharides [4] isolated 'from pig blood-group substance H. This paper is concerned with elucidation of the structure of more complex oligosaccharides, having from seven to eleven monosaccharides units, isolated after degradation of the same glycoprotein H.…”

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confidence: 99%

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The Structure of Carbohydrate Chains of Blood‐Group Substance

Derevitskaya

Arbatsky

Kochetkov

1978

European Journal of Biochemistry

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Twenty individual higher reduced oligosaccharides, having from seven to eleven monosaccharide units, were isolated after sodium borohydride degradation of blood-group substance H from pig stomach linings. Anion-exchange high-pressure liquid chromatography appears to be a very convenient and effective method for this kind of higher oligosaccharide mixtures separation. The oligosaccharide structures were determined by means of periodate oxidation, methylation analysis, partial acid and enzymic hydrolysis. It has been found that all the oligosaccharides investigated can be divided into four series. The oligosaccharides belonging to each series have the common oligosaccharide fragment to which terminal L-fucose and/or N-acetyl-D-glucosamine residues are attached. Comparison of all the oligosaccharide structures, including tri, penta and hexasaccharides described earlier, shows that .the lower oligosaccharides represent the structural element of the higher oligosaccharides.Recently a high degree of heterogeneity of carbohydrate chains of blood-group substances from different sources has been demonstrated [l -61. The treatment of glycoproteins with alkaline sodium borohydride [7] results in the cleavage of practically undegraded carbohydrate chains as oligosaccharides (see, however [S]). The separation of a complicated oligosaccharide mixture using anion-exchange chromatography in borate buffer 191 gives rise to individual oligosaccharides. The elucidation of their structure makes it possible to draw a more definite conclusion about the carbohydrate chains of bloodgroup substances.Earlier we have reported the structure of trisaccharides [3], penta and hexasaccharides [4] isolated 'from pig blood-group substance H. This paper is concerned with elucidation of the structure of more complex oligosaccharides, having from seven to eleven monosaccharides units, isolated after degradation of the same glycoprotein H.

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Section: Discussionmentioning

confidence: 99%

Section: The Structure Of Oligosaccharidesmentioning

confidence: 95%

Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

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The Structure of Carbohydrate Chains of Blood‐Group Substance

Derevitskaya

Arbatsky

Kochetkov

1978

European Journal of Biochemistry

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“…The oligosaccharide mixtures were chromatographed on a Sephadex G-50 column (1.5 x 20 cm) or a TSK-HW40 column (0.8 x 53 cm) calibrated with the following standard mono-and oligosaccharides: GalNAc-ol (1), Gal(fll-3)GalNAc-ol (2) [26], GlcNAc(~I-4)Gal(,81-3)GalNAc-ol (3) [26], Fuc(~l-2)Gal(fll-3)[GlcNAe(cd-4)Gal(,81-4)GleNAc(fll-6)]GalNAc-ol (4) [27]. The oligosaccharides were eluted with water and detected either by measuring UV adsorbtion at 200 nm or the radioactivity of the fractions.…”

Section: Chromatography Of Oligosaccharidesmentioning

confidence: 99%

Mucin‐type glycoprotein from Drosophila melanogaster embryonic cells: characterization of carbohydrate component

et al. 1996

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Glycoprotein Analysis: General Methods

Debray¹,

Spik²

2000

Encyclopedia of Analytical Chemistry

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Glycosylation is a common co‐ and post‐translational modification of a protein which may have profound effects on protein structure and function. Many biologically interesting proteins are glycosylated at their asparagine, serine, and threonine residues. Glycosylation has now been recognized as being more ubiquitous and structurally varied than all other types of post‐translational modifications combined. The glycosylation pattern of a glycoprotein is not random but is dependent on cell type, physiological conditions and, in some cases, disease states. Carbohydrate chains or glycans attached to the peptide backbone are classified according to the nature of the linkage to the peptide and their structure; both of these parameters allow the definition of common cores. In addition to the extreme structural diversity and complexity of glycan structures, one feature of protein glycosylation is the presence at a single site of any one of a number of glycan structures. This property gives rise to an extremely heterogeneous population of glycoproteins, termed glycoforms. The complexity of the glycan structures, the multiple substitutions (microheterogeneity) at glycosylation sites, and the structural diversity associated with the protein backbone itself represent an enormous task for analytical structural studies. Indirect methods such as immunological approaches using antibodies or lectins provide some structural information concerning the nature of glycans. Prior to their structural study, glycans have to be released from the protein backbone by enzymatic or chemical methods. Different endoenzymes such as N ‐glycanase ® allow a complete deglycosylation of glycoproteins, providing a pool of oligosaccharides which may be further fractionated. Establishment of the site heterogeneity and assessment of the different glycoforms require isolation and analysis of the individual glycopeptides generated after hydrolysis with specific proteases. Fractionation of glycans or glycopeptides can be achieved by different high‐performance liquid chromatography (HPLC) or electrophoretic procedures. Lectins, due to their extreme specificities with regard to monosaccharide or oligosaccharide motifs, represent powerful tools for sequential glycan fractionation. Traditionally, a complete structural analysis of the glycan structures, including determination of the carbohydrate sequence and the sugar linkage, has been a tedious, multidisciplinary task. Characterization and determination of the relative amount of individual constituent monosaccharides is generally obtained by gas–liquid chromatography (GLC) after hydrolysis of the oligosaccharide chain. Information concerning the nature of linkages and branching points is furnished by the methylation procedure. Nevertheless, these chemical sequencing methods often necessitate milligrams of material. To progress from this situation, sensitive physicochemical or enzymatic methods have been developed. The nuclear magnetic resonance (NMR) study of oligosaccharides, even of the less sensitive of the physicochemical techniques, is extremely powerful because it allows determination in a mixture of glycans, the complete structure of individual glycans including nature of monosaccharides, sequence, type of linkages, anomericity and branching points. The recent advances in mass spectrometry (MS) techniques, mainly matrix‐assisted laser desorption/ionization (MALDI) or electrospray ionization (ESI), have provided very sensitive means for the analysis of oligosaccharides and glycopeptides. The gain in sensitivity associated with a minimum number of sample manipulation steps allows work at the submicrogram level. The use of enzyme reagents is rapidly becoming popular in modern carbohydrate analysis because of their inherent selectivities for a sugar substrate and its linkage type. Exoglycosidases can be used in conjunction with other methods such as MALDI/MS or fluorophore‐assisted carbohydrate electrophoresis (FACE) separation. Complete structural information is now feasible for low‐microgram and submicrogram quantities of a glycoprotein; this quality of performance places the field of carbohydrate analysis closer to the sequencing methods available for other biomolecules, proteins or nucleic acids.

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The Structure of Pentasaccharides and Hexasaccharides from Blood Group Substance H

Cited by 50 publications

References 11 publications

The Structure of Carbohydrate Chains of Blood‐Group Substance

The Structure of Carbohydrate Chains of Blood‐Group Substance

Mucin‐type glycoprotein from Drosophila melanogaster embryonic cells: characterization of carbohydrate component

Glycoprotein Analysis: General Methods

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