Synthesis and structural analysis using 2-D NMR of sialyl Lewis X (SLex) and Lewis X (Lex) oligosaccharides: ligands related to E-selectin [ELAM-1] binding.

Ball, Graham E.; O'Neill, Roger A.; Schultz, Joanne E.; Lowe, John B.; Weston, Brent W.; Nagy, Jon O.; Brown, E. G.; Hobbs, Christopher; Bednarski, Mark D.

doi:10.1021/ja00039a080

Cited by 100 publications

(27 citation statements)

References 1 publication

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“…4D) by the presence of an additional N-acetyl signal at d 2.033 and the V H3a and V H3e resonances at d 1.797 and d 2.761, respectively, when comparing the spectrum to that of 6. Although the offresonance ROESY spectrum (not shown) did not show cross peaks between V H3 and IV H3 as reported in the literature [25], the a-2,3-linkage between V and IV became evident from the TOCSY (100 ms) spectrum (Fig. 5D).…”

Section: D and 2dsupporting

confidence: 74%

Enzymatic synthesis of the core-2 sialyl Lewis X O-glycan on the tumor-associated MUC1a’ peptide

Gallego¹,

Dudziak²,

Kragl³

et al. 2003

Biochimie

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Starting from a tumor-associated synthetic MUC1-derived peptide MUC1a' and using a completely enzymatic approach for the synthesis of the core-2 sialyl Lewis X glycopart, the following glycopeptide was synthesized:First, polypeptide N-acetylgalactosaminyltransferase 3 was used to site-specifically glycosylate MUC1a' to give MUC1a'-GalNAc. Then, in a one-pot reaction employing b-galactosidase and core-2 b6-N-acetylglucosaminyltransferase the core-2 O-glycan structure was prepared. The core-2 structure was then sequentially galactosylated, sialylated, and fucosylated by making use of b4-galactosyltransferase 1, a3-sialyltransferase 3, and a3-fucosyltransferase 3, respectively, resulting in the sialyl Lewis X glycopeptide. The overall yield of the final compound was 23% (3.2 mg, 1.4 µmol). During the synthesis three intermediate glycopeptides containing O-linked GalNAc, Gal(b1-4)GlcNAc(b1-6)[Gal(b1-3)]GalNAc, and Neu5Ac(a2-3)Gal(b1-4)GlcNAc(b1-6)[Gal(b1-3)]GalNAc, respectively, were isolated in mg quantities. All products were characterized by mass spectrometry and NMR spectroscopy.

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Section: D and 2dsupporting

confidence: 74%

Enzymatic synthesis of the core-2 sialyl Lewis X O-glycan on the tumor-associated MUC1a’ peptide

Gallego¹,

Dudziak²,

Kragl³

et al. 2003

Biochimie

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“…However, it has not been used as a distance constraint, since no build-up procedure at different angles 0 was performed. The number of distance constraints obtained by offresonance ROESY is much larger than what is usually derived by classical procedures for such molecules (Ball et al, 1992;Lin et al, 1992;Miller et al, 1992;Mukhopadhyay et al, 1994). As stated above and as can be seen in Figs.…”

Section: Determination Of Interproton Distances and Correlation Timesmentioning

confidence: 78%

Solution structure of a LewisX analogue by off-resonance 1H NMR spectroscopy without use of an internal distance reference

Berthault¹,

Birlirakis²,

Rubinstenn

et al. 1996

J Biomol NMR

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A recent 1H NMR method has been applied to the determination of the solution structure and internal dynamics of a synthetic mixed C/O trisaccharide related to sialyl Lewis(x). Varying the rf field offset in ROESY-type experiments enabled the measurement of longitudinal and transverse dipolar cross-relaxation rates with high accuracy. Assuming that for each proton pair the motion could be represented by a single exponential autocorrelation function, it was possible to derive geometrical parameters (r) and dynamic parameters (tau(cp)). With this assumption, 224 cross-relaxation rates have been transformed into 30 interproton distance constraints and 30 dipolar correlation times. The distance constraints have been used in a simulated-annealing procedure. This trisaccharide exhibits a structure close to the O-glycosidic analogue, but its flexibility seems highly reduced. On the basis of the determined structure and dynamics, it is shown that no conformational exchange occurs, the molecule existing in the form of a unique family in aqueous solution. In order to assess the quality of the resulting structures and to validate this new experimental procedure of distance extraction, we finally compare these solution structures to the ones obtained using three different sets of distances deduced from three choices of internal reference. It appears that this procedure allows the determination of the most precise and accurate solution.

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“…There are numerous reports in the literature that deal with the chemical [12][13][14][15][16][17] or chemoenzymatic 18 preparation of Le x analogues as well as that of Le x intermediate building blocks to be further converted into the Sialyl Le x tetrasaccharide. It has been established early on by Jacquinet and Sinaÿ 12 as well as by Hindsgaul et al 13 that the glycosylation at O-4 of N-acetylglucosamine in such syntheses was often difficult.…”

Section: Synthesis Of Trisaccharide 10: Additional Results On the Glymentioning

confidence: 99%

Synthesis of a BSA-Lex glycoconjugate and recognition of Lex analogues by the anti-Lex monoclonal antibody SH1: The identification of a non-cross reactive analogue

Wang

Asnani

Auzanneau

2010

Bioorganic & Medicinal Chemistry

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Synthesis and structural analysis using 2-D NMR of sialyl Lewis X (SLex) and Lewis X (Lex) oligosaccharides: ligands related to E-selectin [ELAM-1] binding.

Cited by 100 publications

References 1 publication

Enzymatic synthesis of the core-2 sialyl Lewis X O-glycan on the tumor-associated MUC1a’ peptide

Enzymatic synthesis of the core-2 sialyl Lewis X O-glycan on the tumor-associated MUC1a’ peptide

Solution structure of a LewisX analogue by off-resonance 1H NMR spectroscopy without use of an internal distance reference

Synthesis of a BSA-Lex glycoconjugate and recognition of Lex analogues by the anti-Lex monoclonal antibody SH1: The identification of a non-cross reactive analogue

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