Structure de la <i>N</i>-acétyllactosamine (acétamido-2 désoxy-2 <i>O</i>-β-<scp>D</scp>-galactopyrannosyl-4a-<scp>D</scp>-glucopyrannose)

Longchambon, F.; Ohanessian, J.; Gillier‐Pandraud, H.; Duchet, D.; Jacquinet, Jean‐Claude; Sînaÿ, Pierre

doi:10.1107/s0567740881003658

Cited by 33 publications

(10 citation statements)

References 4 publications

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“…Therefore, three additional families, apart of the major one described for N-acetyl-lactosamine 15 16 When the comparison between expected and experimental vicinal proton-proton couplings was performed, the calculated couplings notoriously deviated from the experimental results, highlighted in Tables 1 and 2. In fact, the MM MM3 * -based calculations predict a higher percentage of the unusual anti-W conformers around the glycosidic linkage than those actually existing.…”

Section: Resultsmentioning

confidence: 95%

“…Therefore, B, C and D adopt the regular syn-exo-anomeric region around U, as for natural O-glycosyl compounds. X-ray analysis of N-acetyl-lactosamine, 15 has shown that this compound adopts minimum B in the solid state. Therefore, according to the MM MM3 * calculations, N-acetyllactosamine and its C-glycosyl analogue show similar U, values, but differ around 180°for W. Moreover, MD simulations revealed that the major minima were conformationally stable during the time scale of the simulations (3 ns).…”

Section: Resultsmentioning

confidence: 99%

“…These results support, in a definitive manner, the exclusive recognition of syn-type conformations around both U/W torsió n angles of b-linked galactosides by galectins. 15 In fact, in the X-ray structure of different lactose derivatives bound to galectins, 15 besides the typical key interactions between the nonreducing end galactoside residue (hydrogen bonds and aromatic-sugar interactions), there is a key hydrogen bond between the OH-3 group of the Glc(GlcNAc) and a properly oriented polar lateral chain of the polypeptide moiety. 27 This key hydrogen bond is only possible if the natural disaccharide (or glycomimetics thereof) adopts a syn-type around U/W.…”

Section: The Bound State the Interaction Of 1 With Viscumin (Mistletmentioning

confidence: 99%

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The conformation of the C-glycosyl analogue of N-acetyl-lactosamine in the free state and bound to a toxic plant agglutinin and human adhesion/growth-regulatory galectin-1

Garcı́a-Aparicio

Sollogoub

Blériot

et al. 2007

Carbohydrate Research

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Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 99%

Section: The Bound State the Interaction Of 1 With Viscumin (Mistletmentioning

confidence: 99%

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The conformation of the C-glycosyl analogue of N-acetyl-lactosamine in the free state and bound to a toxic plant agglutinin and human adhesion/growth-regulatory galectin-1

Garcı́a-Aparicio

Sollogoub

Blériot

et al. 2007

Carbohydrate Research

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“…The minimum energy calculations indicate that the conformation and steric arrangement of the two disaccharides are essentially identical. X-ray crystallographic analyses of lactose and N-acetyl-lactosamine [33,34] …”

Section: Discussionmentioning

confidence: 99%

Binding of Disaccharides by Peanut Agglutinin as Studied by Ultraviolet Difference Spectroscopy

Neurohr

Bundle

Young

et al. 1982

European Journal of Biochemistry

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The binding of the disaccharides methyl b-D-lactoside and 2-acetamido-2-deoxy-3-O-(~-~-galactopyranosyI)-fi-D-galactopyranose [~-D-Gal-(l+3)-~-GalNAc] to peanut agglutinin was studied by ultraviolet difference spectroscopy. The magnitude of the difference spectra varied with the concentration of the carbohydrates; association constants and thermodynamic parameters were determined from titration experiments at different temperatures. The enthalpy and entropy changes for binding of methyl b-D-lactoside were found to bethe observed thermodynamic parameters were AH" = -78 5 kJ mol-', AS" = -177 f 16 J mol-' K-'. For both disaccharides, the enthalpy change upon binding to the lectin is much larger than that found for the binding of These studies showed that ultraviolet difference spectroscopy is a useful and powerful tool for the study of sugar binding to this lectin. By observing directly the changes in the ultraviolet spectrum of the protein upon binding of carbohydrates, the need for bulky fluorescent or other spectroscopic reporter groups attached to the carbohydrate is eliminated together with their possible perturbations. We have therefore used this method to study the thermodynamics of oligosaccharide binding to peanut agglutinin, employing the methyl p-glycoside of lactose and fl-D-Gal-(l+3)-u-GalNAc, which has been established as the best inhibitor of this lectin

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“…The reported solid state (20) conformation for p-lactose as determined by X-ray diffraction studies is + = 50" and $ = lo0, in qualitative agreement with the solution studies. However, the solid state conformation for p-lactosamine is + = 30" and $ = -20°, significantly different from the solution studies (21). Furthermore, Kochetkov and co-workers, studying related p-1,4 linkages, have presented evidence that a model considering a single predominant conformer (22), as in the studies above, is not sufficient to account for the experimental data and so the conformational preference(s) of these P-1,4 linkages still requires further investigations.…”

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confidence: 78%

Syntheses of model oligosaccharides of biological significance. 9. Syntheses of trideuteriomethyl di-3,6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranoside: the I antigen branch-point trisaccharide and related disaccharides

Whitfield¹,

Ruzicka²,

Carver³

et al. 1987

Can. J. Chem.

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. Can. J. Chem. 65,693 (1987). ' The title trisaccharide, 13c, was synthesized, as well as its two component disaccharides, 10c and l l c . Four disaccharides, 3c, 4c, 5c, and 7c, were also prepared to serve as model compounds for the investigation of the 3-dimensional structure of more complex oligosaccharides. The P-1,3 linkage was formed in 75% yield by coupling 3,4,6-tri-0-acetyl-2-deoxy-2-phthalimido-P-D-glucopyranosyl bromide (9) with trideuteriomethyl2-O-benzoyl-4,6-benzylidene-~-~-galactopyranoside (2a), using silver trifluoromethanesulphonate as a promoter in the presence of the base 2,6-di-tert-butyl-4-methylpyridine. Using a silver zeolite as a promoter under a variety of conditions, both a-1,3 and P-1,3 linkages were formed. The P-1,6 linkages were prepared in high yield using 9 and silver zeolite with either trideuteriomethyl 2,3-di-0-benzoyl-P-D-galactopyranoside Chem. 65, 693 (1987). On a synthCtisC le trisaccharide mentionnC dans le titre (13c) ainsi que les deux disaccharides qui le foment (10c et l l c ) . On a aussi prCparC les quatre disaccharides 3c, 4c, 5c et 7c comme composCs modkles pour 1'Ctude de la structure tridimensionnelle d'oligosaccharides plus complexes. On a form6 la liaison P-1,3 avec un rendement de 75% en procCdant au couplage du bromure de tri-0-acttyl-3,4,6 dCoxy-2 phtalimido-2 P-D-glycopyrannosyle (9) avec le 0-benzoyl-2 benzylidkne-4,6 P-D-galactopyrannoside de trideut6romCthyle (2a), sous l'influence du trifluoromCthanesulfonate d'argent comme promoteur de la reaction et en prksence de di-tert-butyl-2,6 mCthyl-4 pyridine comme base. Si on utilise le zeolite d'argent comme promoteur, sous diverses conditions, il y a formation des liaisons a-1,3 ainsi que p-1,3. On a prCparC les liaisons P-1 ,6 avec de bons rendements en faisant rCagir le composC 9, en prCsence de zColite d'argent comme promoteur, avec soit le di-0-benzoyl-2,3 P-D-galactopyrranoside de trideutCromCthyle (86) soit le 0-benzoyl-2 0-(tri-0-acCtyl-3,4,6 dCoxy-2 phtalimido-2 P-D-g1~~0pyrann0~yl)-3 P-D-galactopyrannoside de trideutCromCthyle ( l l b ) . On a utilisC le bromure de tri-0-benzyl-2,3,4 a-L-fucopyrannosyle (lb) pour la fucosylation, catalysCe par les ions halogknures, du composC 2a ou de son isomkre 0-benzoyle-3 (26). Les glycosylations des bromures de di-0-acCtyl-3,6 0-(tCtra-0-acCtyl-2,3,4,6 P-D-gala~topyranno~y1)-4 dCoxy-2 phtalimido-2 P-D-glucopyrannosyle (66) et de 0-(tetra-0-acCtyl-2,3,4,6 P-D-galactopyrannosy1)-4 tri-0-acCtyl-2,3,6 a -D -g l~~~p y r a n n~~y l e (50) par l'heptadeutCro-isopropanol se font sous l'influence du zeolite d'argent comme promoteur.[Traduit par la revue]As part of our program of studies of complex oligosaccharides, in particular those structures related to neoplasia (I), we have synthesized trisaccharide 13c and several related disaccharides 3c, 4c, 5c, 7c, and 10c as their P-glycosides. These anomerically pure oligosaccharides are suitable for the elucidation of their 3-dimensional structures by nrnr spectroscopic techniques (2).1i is our that to understand the biol...

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Structure de la N-acétyllactosamine (acétamido-2 désoxy-2 O-β-D-galactopyrannosyl-4a-D-glucopyrannose)

Cited by 33 publications

References 4 publications

The conformation of the C-glycosyl analogue of N-acetyl-lactosamine in the free state and bound to a toxic plant agglutinin and human adhesion/growth-regulatory galectin-1

The conformation of the C-glycosyl analogue of N-acetyl-lactosamine in the free state and bound to a toxic plant agglutinin and human adhesion/growth-regulatory galectin-1

Binding of Disaccharides by Peanut Agglutinin as Studied by Ultraviolet Difference Spectroscopy

Syntheses of model oligosaccharides of biological significance. 9. Syntheses of trideuteriomethyl di-3,6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranoside: the I antigen branch-point trisaccharide and related disaccharides

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