Synthesis in the glycosciences II
This Thematic Series “Synthesis in the glycosciences II” follows the first serieslaunched in 2010. The many different works impressively demonstrate the variety in the glycosciences. Fantasy and imagination have led to novel glycoconjugate architectures and glycobiological experiments. Expertise and rational planning have allowed the utilization of carbohydrates in stereoselective synthesis and the employment of enzymes in oligosaccharide synthesis. Analytical and pharmacological knowhow have disclosed polysaccharide and glycoconjugate structures, their biological effects and their potential as carbohydrate drugs. Boldness and interdisciplinary communication have opened the field for many medical applications benefitting human health, such as in tumor diagnosis, tumor treatment and vaccination.
See also the Thematic Series:
Synthesis in the glycosciences
Multivalent glycosystems for nanoscience
See videos about glycoscience at Beilstein TV.
- Full Research Paper
- Published 20 Mar 2012
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Figure 1: Monobenzylated methyl α- and β-D-gluco- and galactopyranoside acceptors 1–6.
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Figure 2: Benzylated glycopyranosyl halide donors 7–9.
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Scheme 1: Synthesis of monobenzylated glucopyranosyl acceptors 1–4. Reagents and conditions: (a) Benzaldehyde...
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Scheme 2: Synthesis of 3-O-monobenzylated gluco- und galactopyranosyl acceptors 5 and 6. Reagents and conditi...
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Scheme 3: Synthesis of 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl chloride (8) and 2,3,4,6-tetra-O-benzyl-α-...
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- Letter
- Published 20 Mar 2012
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Figure 1: (a) Schematic representation of a heteroglycocluster of the 2:2 series containing Man and Fuc. (b) ...
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Scheme 1: Synthesis of heteroglycoclusters of the 2:2 series. Reagents and conditions: (i) 0.1% TFA in H2O; (...
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Scheme 2: Synthesis of heteroglycoclusters of the 3:1 series. Reagents and conditions: (i) 1a, 2a or 3a, 0.1%...
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- Published 27 Mar 2012
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Figure 1: Schematic diagram of the network of hydrogen bonds in the binding pocket of the complex between MBP...
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Figure 2: 2-19F-Maltose reporter system: Nonstereoselective fluorine labeling at the 2-position of maltose le...
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Scheme 1: Syntheses of maltose derivatives; reagents and conditions: (a) Ac2O, Pyr, 97%; (b) HBr, AcOH, 99%; ...
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Scheme 2: Synthesis of the maltose- and galacto-type derivatives; reagents and conditions: (a) TBDMS-Cl, imid...
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Figure 3: 1-D 19F NMR: Experimental demonstration of differential binding of gluco- and manno-type 2-F-labele...
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Figure 4: 19F NMR expansion (of Figure 3) of the gluco-type region of the 2-F-maltose reporter system.
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Figure 5: Competitive titration with the 2-F-maltose reporter system and 19F NMR: only the important section ...
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- Letter
- Published 28 Mar 2012
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Scheme 1: Electrochemical conversion of thioglycosides to glycosyl triflates.
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Figure 1: 1H NMR spectrum of glycosyl triflate 2a.
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Scheme 2: Triflic acid mediated isomerization of β-glycoside.
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- Published 05 Apr 2012
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Figure 1: Structure of trehalose (1), validoxylamine A (2), 1-thiatrehazolin (3), trehalostatin (4), casuarin...
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Figure 2: Structure of nojirimycin-based (7, 8) and pyrrolidine-based (9) leads.
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Figure 3: Structures of potential inhibitors 10–21.
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Scheme 1: Synthesis of nojirimycin-based inhibitors 10,12 and 13. Reagents and conditions: (a) H2, Pd/C, NH4O...
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Scheme 2: Synthesis of pyrrolidine derivatives 14, 16, 17 and 19. Reagents and conditions: (a) H2, Pd(OH)2/C,...
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Scheme 3: Synthesis of pyrrolidines 20 and 21. Reagents and conditions: (a) H2, Pd/C, MeOH, HCl; (b) octanal,...
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Figure 4: Histogram of the inhibitory activity of compounds 7–10, 12–14, 16 and 20. Derivatives 10, 14 and 16...
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- Full Research Paper
- Published 10 Apr 2012
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Figure 1: Synthetic route to transform oxyglycal I to a septanoside V.
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Scheme 1: Reaction conditions: (i) NaOMe, PhMe, reflux, 8 h; (ii) methyl acrylate (for 3); tert-butyl acrylat...
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Scheme 2: Reaction conditions: (i) phenylboronic acid (for 8); 4-methoxyphenylboronic acid (for 9); 3-methylp...
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Scheme 3: Reaction conditions: (i) phenylacetylene (for 11); oct-1-yne (for 12); Pd(PPh3)2Cl2 (20 mol %), CuI...
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Scheme 4: Reaction conditions: (i) Pd/C (10 %), H2, MeOH, rt, 24 h; (ii) NaBH4, MeOH, 0 °C to rt, 3 h.
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- Published 13 Apr 2012
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Figure 1: Polysaccharide structures of pullulan and dextran cyanoethylation with acrylonitrile and NaOH as ca...
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Figure 2: ATR–IR spectra of (a) dextran, 6 kDa, and cyanoethyldextrans (b–d) CED-1–3.
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Figure 3: ATR–IR spectra of (a) pullulan, 100 kDa, and cyanoethylpullulans (b–d) CEP-1–3.
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Figure 4: 1H NMR spectra (300 MHz) of (a) CED-2 (DSNMR(1) = 1.81) in D2O; (b) dextran, native in D2O; (c) CED...
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Figure 5: 1H NMR spectra (400 MHz) of (a) CEP-2 (DSNMR(3) = 1.31) in D2O; (b) pullulan, native in D2O; (c) CE...
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Figure 6: Gas chromatogram of hydrolyzed and trimethylsilylated cyanoethylglucans; (a) CED-1 (DSGC = 0.74); (...
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Figure 7: Experimentally determined substituent distribution in the glucosyl units (glc) of cyanoethyldextran...
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Figure 8: Experimentally determined substituent distribution in the glucosyl units (glc) of cyanoethylpullula...
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Figure 9: TEM micrograph of iron oxide nanoparticles prepared from an aqueous dispersion.
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Figure 10: SEM micrographs of CEP-3 with iron oxide nanoparticles, (Table 3, entry 2).
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Figure 11: TEM micrograph of (a) uncoated iron oxide nanoparticles; (b) of CEP-3 + iron oxide nanoparticles (n...
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Figure 12: ESI Fe distribution maps of CEP-3 with iron oxide nanoparticle (Table 3, entry 1). (A) Net Fe, shown in re...
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- Full Research Paper
- Published 18 Apr 2012
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Scheme 1: Orthogonal strategy introduced by Ogawa et al.
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Scheme 2: Determination of the AP activation pathways.
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Scheme 3: AP building blocks in oligosaccharide synthesis.
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- Published 24 Apr 2012
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Figure 1: Absolute chemical structures of M. fermentans α-glycolipid antigens, GGPL-I and GGPl-III (GGPL: Gly...
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Scheme 1: An established synthetic pathway to α-glycosyl-sn-glycerols 4a and 5a. A reagent combination of CBr4...
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Scheme 2: Syntheses of GGPL-I homologue I-a and its isomer I-b. Conditions: (a) K2CO3, CH3OH; (b) cesium palm...
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Figure 2: 1H NMR spectra of I-a and I-b (500 MHz, 25 °C, CDCl3/CD3OD 10:1). The assignment of sn-glycerol met...
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Figure 3: Distributions of gg, gt and tg-conformers in 3-substituted sn-glycerols at 11 mM in solutions of CD...
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Figure 4: Distributions of gg, gt and tg-conformers in 1-substituted sn-glycerols. In these sn-isomers, Φ1 an...
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Figure 5: A common conformational property of GGPL-I and DPPC. The tail lipid moiety favors two gauche-confor...
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- Full Research Paper
- Published 30 Apr 2012
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Scheme 1: Reactivity of N-glycosyl nitrones 1 towards dipolarophiles and nucleophiles leading to products of ...
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Scheme 2: Additions of lithiated alkoxyallenes to L-erythrose-derived nitrone 1a leading to 3,6-dihydro-2H-1,...
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Figure 1: By-products 4 and 5 isolated from the reaction of nitrone 1a with lithiated methoxyallene.
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Figure 2: Single-crystal X-ray analysis of (3R)-3a (ellipsoids are drawn at a 50% probability level).
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Figure 3: Model proposed for the addition of lithiated allenes to nitrone 1a.
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Scheme 3: Speculative mechanistic suggestion for the formation of tetrasubstituted pyrrole derivative 5.
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Scheme 4: Introduction of a 5-hydroxy group into 1,2-oxazine derivatives 3 by a hydroboration/oxidation proto...
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Scheme 5: Samarium diiodide-induced ring opening of tetrahydro-2H-1,2-oxazine derivatives 12 and 13.
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Scheme 6: Reaction of tetrahydro-2H-1,2-oxazine 18 with samarium diiodide. (a) NaH (1.4 equiv), BnBr (1.2 equ...
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Scheme 7: Attempted synthesis of pyrrolidine derivatives from precursor 13. (a) TMSCl (1.5 equiv), imidazole,...
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Scheme 8: Synthesis of TBS-protected tetrahydro-2H-1,2-oxazine 27 and its transformation into pyrrolidine der...
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- Published 02 May 2012
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Scheme 1: Different strategies to access C-glycosides starting from 1-substituted glycals.
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Scheme 2: Sonogashira–Hagihara reaction of 1-iodo-2-chloroglucal 12 with phenylacetylene (8a) to afford 13.
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- Published 08 May 2012
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Figure 1: Structure of glycyrrhizin (GL), carbenoxolone (CBX), and spacer analogues.
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Scheme 1: Synthesis of methyl 2-haloethyl 1-thio-glucuronide derivatives: (a) 1 M NaOMe, MeOH, −60 °C to −45 ...
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Scheme 2: Synthesis of thioalkylglucuronide GA derivatives: (a) DMF, DIPEA, 45–50 °C, 16 h, 79%; (b) TEA, Ac2...
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Figure 2: 400 MHz 1H NMR expansion plots of the carbohydrate region of compound 11, recorded at various tempe...
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Scheme 3: Synthesis of 3-thioether-bridged glucuronide derivatives: (a) K2CO3, acetone, 60%; (b) 0.8 M NaOMe,...
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- Published 09 May 2012
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Scheme 1: Reaction scheme of terminal galactose in poly-LacNAc-glycans (1a–d) or GalNAc in LacDiNAc (2) by ga...
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Figure 1: Conversion of 3b (squares) to the corresponding α,β-unsaturated aldehyde 7b (triangles) and side pr...
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Scheme 2: Enzymatic modifications of oxidised poly-LacNAc oligomers. A: Elongation of LacNAc-6-aldehyde 3a by...
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Scheme 3: A: Labelling of poly-LacNAc oligomers 3a–c and 9a with biotin hydrazide derivative BACH (12) yieldi...
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Figure 2: HPLC analysis for the conversion of modified LacNAc oligomers 3a, 15a, and 7a with β3-GlcNAc-transf...
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Scheme 4: Chemical conjugation of oxidised poly-LacNAc oligomers with heptasaccharide–linker–NH2 (17) by redu...
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- Published 14 May 2012
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Figure 1: The papulacandins.
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Scheme 1: (a) H2SO4, MeOH, reflux, 18 h, 3: 98%; (b) BnBr, K2CO3, acetone, reflux, 18 h; (c) LiAlH4, THF, rt,...
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Scheme 2: (a) NaOMe in MeOH, MeOH, rt, 1 h, 96%; (b) (t-Bu)2Si(OTf)2, pyridine, DMF, −40 °C to rt, 2 h, 90%; ...
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Scheme 3: (a) Pd2(dba)3∙CHCl3, NaOt-Bu, toluene, 50 °C, 6–20 h, 23: 72%, 24: 79%, 25: 62%; (b) DiBAL-H, CH2Cl2...
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Scheme 4: (a) Pd/C, NaHCO3, H2, THF, rt, 1.5 h, 98%; (b) MOMCl, DiPEA, DMAP, CH2Cl2, rt, 4 d, 78%; (c) TBAHF,...
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- Published 21 May 2012
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Figure 1: Carbohydrate arrays on polystyrene slides can be obtained by noncovalent immobilisation of tritylat...
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Scheme 1: Synthesis of the tritylated compounds 3 [28], 5 and 7: (a) dichloromethane, 2.5 h, rt, 98%, (b) HBTU/DI...
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Figure 2: Comparison of the polystyrene and glass surfaces with and without aluminium backing by matrix-free ...
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Scheme 2: The Man–Trt compound 5 forms the disulfide 8 during UV ionisation in MALDI-TOF MS analysis.
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Figure 3: Limit-of-detection analysis of 5 on aluminium-backed glass and polystyrene slides. Both systems sho...
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Figure 4: Comparison of MALDI-TOF MS spectra on the aluminium-backed polystyrene and glass slides after washi...
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Figure 5: Photo of the aluminium strip on the back of the polystyrene support.
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- Published 23 May 2012
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Figure 1: Saponins from A. gypsophiloides 1, R = OH and 2, R = H.
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Figure 2: Part of a 2D ROESY spectrum of compound 1. The corresponding parts of the 1H NMR spectrum are shown...
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Figure 3: Key ROESY (dashed line) correlations for compound 1.
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Figure 4: Part of the HMBC spectrum of compound 1. 1H and 13C NMR spectra are shown along the horizontal and ...
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Figure 5: IL-6 production of primary endotheliocytes in the presence of compounds 1 and 2. Error bars represe...
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Figure 6: Growth inhibition zones for F. neoformans IGC 3957 in the presence of compounds 1 and 2 at pH 4.0. ...
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- Full Research Paper
- Published 29 May 2012
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Scheme 1: Synthesis of (4-{[(β-D-galactopyranosyl)oxy]methyl}furan-3-yl)methyl hydrogen sulfate (GSF, 5) and ...
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Figure 1: Effects of increasing concentrations of (4-{[(β-D-galactopyranosyl)oxy]methyl}furan-3-yl)methyl hyd...
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Figure 2: Inhibition of adhesion of WM-115 cells to fibrinogen (A), or to fibronectin (B) with increasing con...
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Figure 3: Inhibition of adhesion of melanoma cells WM-115 to fibronectin-coated plastic by 5 mM (4-{[(β-D-gal...
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Figure 4: In silico blind-docking (A, B) and molecular dynamic simulations (C) of (4-{[(β-D-galactopyranosyl)...
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Figure 5: Intact cell monolayers of WM-115 cells in 12-well plates were wounded with a 100 µL pipette tip and...
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Figure 6: A: Zymograms (color inverted) of serum-free conditioned medium of melanoma cells treated with (4-{[...
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Figure 7: Adhesion of HBMEC-60 to extracellular matrix proteins. Prior to the adhesion experiments, HBMEC-60 ...
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Figure 8: Effect of (4-{[(β-D-galactopyranosyl)oxy]methyl}furan-3-yl)methyl hydrogen sulfate (GSF) on transmi...
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Figure 9: Influence of saccharide mimetics on endothelial networking (matrigel-assay) (A) and tube formation ...
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- Review
- Published 30 May 2012
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Figure 1: Tumor-associated glycosylation on MUC1 tandem repeat peptides.
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Scheme 1: Synthesis of MUC1 tetanus toxoid protein conjugate vaccines.
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Scheme 2: TN, T and sialyl-T MUC1 Pam3Cys two-component vaccines.
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Scheme 3: Preparation of RNase C by sequential NCL.
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Scheme 4: Preparation of an EPO analogue modified with complex type N-glycans at position 24 and 30.
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Scheme 5: Auxiliary-assisted NCL of two glycopeptide fragments.
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Scheme 6: NCL of a glycopeptide fragment, generating valine by desulfurization at the ligation site.
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Scheme 7: Synthesis of homogeneous glycoproteins by chemoenzymatic glycan remodeling.
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Figure 2: Di- and trivalent glycopeptide dendrimers evaluated for FimH inhibition.
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- Full Research Paper
- Published 01 Jun 2012
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Figure 1: Amines used for the synthesis of glycoclusters.
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Scheme 1: Synthesis of glycocluster B5 with isolation of the intermediate diazide 2.
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Scheme 2: Deacetylation of glycoconjugates B1–B6. (a) NaOMe, MeOH.
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Scheme 3: Formation of side-product 5 during the synthesis of 4.
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Figure 2: Dose-response curves for the inhibition of binding of HRP-labeled WGA to covalently immobilized Glc...
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Figure 3: Molecular model of divalent ligand C4 with its two chitobiose moieties occupying two adjacent bindi...
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- Letter
- Published 26 Jun 2012
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Figure 1: First (2) and second (3) generation of dendrimers based on chiral C2-symmetric pyrrolidine 1 and ha...
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Scheme 1: Use of the key intermediate (3S,4S)-1-benzyl-3,4-dihydroxypyrrolidine (6) [31] for the synthesis of pyr...
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Scheme 2: Synthesis of calixarene-based dendrimers 2 and 3. Reagents and conditions: DIPEA, CH2Cl2, 30 °C, 5 ...
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Figure 2: Expansion (about 7 to 3 ppm) of the 1H NMR spectra of (A) the free ligand 2, (B) the sodium picrate...
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Figure 3: Schematic of the inclusion of alkali-metal ions (sodium and potassium) in the polar cavity defined ...
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- Published 11 Jul 2012
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Figure 1: Known types of η6-tricarbonylchromium complexes of sugar derivatives [9-13].
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Scheme 1: Synthesis of glucoside 1l.
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Scheme 2: Deprotection of 2c and enzymatic cleavage of 3.
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Figure 2: ORTEP-plot of the asymmetric unit containing two molecules of compound 2a showing 30% probability e...
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Figure 3: ORTEP-plot of the asymmetric unit showing two molecules of compound 2b and 30% probability ellipsoi...
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Figure 4: ORTEP-plot of the asymmetrical unit showing two molecules of compound 2c and 30% probability ellips...
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Figure 5: ORTEP-plot of the asymmetric unit showing two molecules of compound 2d and 30% probability ellipsoi...
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Figure 6: ORTEP-plot of the asymmetrical unit showing two molecules of compound 2e and 30% probability ellips...
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Figure 7: ORTEP-plot of the asymmetric unit showing three molecules of compound 2j and 30% probability ellips...
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Figure 8: ORTEP-plot of the asymmetric unit showing three molecules of compound 2k and 30% probability ellips...
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Figure 9: ORTEP-plot of the asymmetric unit showing two molecules of compound pR-2m and 30% probability ellip...
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Figure 10: ORTEP-plot of the asymmetric unit showing three molecules of compound pS-2m and 30% probability ell...
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- Published 23 Jul 2012
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Figure 1: Structure of Lex and analogues 2–5.
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Figure 2: Monosaccharide building blocks 6–13.
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Scheme 1: Synthesis of trichloroacetimidate donors 9–11.
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Scheme 2: Synthesis of trisaccharides 26–28 and deprotection reactions giving 3–5.
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- Published 01 Aug 2012
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Figure 1: (A) Conventional approach for the chemical synthesis of sugar nucleotides from sugar 1-phosphates; ...
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Figure 2: Structures of the Manp-1P derivatives (1–8) previously shown [24,25] to be substrates for S. enterica GDP-...
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Scheme 1: Reagents and conditions: (a) CH3I, NaH, DMF, 80%; (b) Ac2O–HOAc–H2SO4, 35:15:1, 81%; (c) EtSH, BF3·...
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Scheme 2: Reagents and conditions: (a) CH3I, NaH, DMF, 76%; (b) Ac2O–HOAc–H2SO4, 35:15:1, 65%; (c) EtSH, BF3·...
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Scheme 3: Reagents and conditions: (a) TrCl, DMAP, pyridine, 85%; (b) DMP, p-TsOH, 76%; (c) CH3I, NaH, DMF, 9...
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Scheme 4: Reagents and conditions: (a) (i) NaOCH3, CH3OH; (ii) TBDPSCl, imidazole, DMF, 78%; (b) BnBr, NaH, T...
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Scheme 5: Reagents and conditions: (a) Ag2O, CaSO4, CH3I, 52%; (b) Ac2O–HOAc–H2SO4, 70:30:1, 96%; (c) EtSH, BF...
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Scheme 6: Reagents and conditions: (a) PPh3, imidazole, I2, 65%; (b) (i) Ac2O–HOAc–H2SO4, 35:15:1; (ii) Pd–C,...
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Figure 3: Reaction catalyzed by GDP-ManPP.
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Figure 4: Structure of modified GDP-Man derivatives 48–52 produced from 9–13.
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Figure 5: Comparison of the relative activity of synthetic Manp-1P analogues 9–13 for GDP-ManPP, with that of...
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Figure 6: Summary of the substrate specificity of GDP-ManPP. Data from previous studies on the enzyme are als...
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- Published 21 Sep 2012
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Figure 1: (a) Synthesis sequence for the preparation of building blocks 4 and 5; (b) Retrosynthetic analysis ...
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Scheme 1: Reagents and conditions: (i) PhI(OAc)2, BF3·Et2O, CH2Cl2, −40 °C; then Ac2O, pyridine; (ii) N2H4·Ac...
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Scheme 2: Reagents and conditions. (i) TMSOTf, DCM, −10 °C, 80%; (ii) NaOMe, MeOH; then KOH, MeOH, 60 °C; the...
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Scheme 3: Automated synthesis of 20. Reagents and conditions: (i) (a) NIS, TfOH, dioxane, DCM, −40 to −20 °C,...
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Scheme 4: Automated synthesis of 16. Reagents and conditions: (i) (a) NIS, TfOH, dioxane, DCM, −40 to −20 °C,...
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Scheme 5: Automated synthesis of 27. Reagents and conditions: (i) (a) NIS, TfOH, dioxane, DCM, −40 to −20 °C,...
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Scheme 6: Automated synthesis of 30. Reagents and conditions: (i) (a) NIS, TfOH, dioxane, DCM, −40 to −20 °C,...
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Scheme 7: Reagents and conditions: (i) 10% DMF in PBS buffer pH 7.5, overnight, 80%.
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- Published 25 Sep 2012
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Scheme 1: Amadori rearrangement.
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Scheme 2: C-Elongation using the sodium cyanide/sodium borohydride and HCN/Pd(BaSO4) method.
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Scheme 3: C-Elongation as well as Amadori rearrangement in the D-gluco series.
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Scheme 4: C-Elongation method by modified Kiliani–Fischer protocol from of D-galactose, D-mannose as well as ...
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Scheme 5: Amadori rearrangement in the D-galacto series.
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Scheme 6: Amadori rearrangement in the D-manno series.
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Scheme 7: Amadori rearrangement in the GlcNAc series.
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- Published 25 Oct 2012
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Figure 1: Examples of naturally occurring iminosugars.
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Figure 2: The chemical structures of (+)-batzellasides A–C (1a–c).
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Scheme 1: Our previous approach to (+)-batzellaside B and retrosynthetic analysis for the new synthetic strat...
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Scheme 2: Reagents and conditions: (a) see [22]; (b) MeONa, MeOH, rt; 98%; (c) (i) p-TsOH, MeOH, rt; (ii) BF3·Et2...
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Scheme 3: Reagents and conditions: (a) (i) K2CO3, MeOH, rt; (ii) TBSCl, Et3N, CH2Cl2, rt; (iii) BnBr, NaH, Bu4...
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- Letter
- Published 26 Nov 2012
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Figure 1: Structures of two novel linkers on different resins.
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Scheme 1: Synthesis of a new acylsulfonamide safety-catch linker. Reagents and conditions: (a) benzaldehyde, ...
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Scheme 2: Functionalization of different resins. Reagents and conditions: (a) Cs2CO3, DMF, TBAI, Merrifield c...
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Scheme 3: Glycosylation and cleavage reactions for analysis. Reagents and conditions: (a) automated glycosyla...
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Scheme 4: Further investigations of safety-catch linker. Reagents and conditions: (a) NaOMe, MeOH; (b) 19, NI...
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- Letter
- Published 10 Dec 2012
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Scheme 1: Synthesis of glycoamino acid derivative 3 and its dimer, from the known mannopyranoside 1.
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Scheme 2: To obtain the glycocystine derivative 3-dimer from the protected cysteine mannopyranoside precursor ...
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Figure 1: In the 1H/13C HMBC NMR spectrum of the S-Fm-protected glycoamino acid derivative 8, protecting-grou...
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Scheme 3: Proposed mechanism for the formation of S-Fm-protected 8 from N-Fmoc-protected 7 according to Rich ...
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- Full Research Paper
- Published 10 Jan 2013
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Figure 1: Azidosugars used in this study. The synthesis of the azidosugars 1–3 was modified from [47,48], compounds 4...
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Scheme 1: Reaction conditions and reagents: (a) Ns-chloride (6.00 equiv), 2,4,6-collidine (12.0 equiv), CH2Cl2...
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Scheme 2: Synthesis of spermine conjugates 20,21 and 24,25. 2-chlorotrityl chloride resin was used as a solid...
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Scheme 3: Synthesis of hexaalkynyl peptoids 26 and 27 on solid supports.
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Scheme 4: Synthesis of a hexa-glycosylated peptoid 28.
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- Letter
- Published 16 Jan 2013
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Scheme 1: Solid-phase synthesis of biopolymers. X represents a reactive site such as an amino group for pepti...
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Figure 1: Different resins used for solid-phase synthesis. (A) Hydrophobic PS resins. (B) Water-compatible re...
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Scheme 2: Design of linker 1. Cleavage by hydrogenolysis from a solid support reveals a conjugation site for ...
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Scheme 3: Synthesis of linker 1. Reactions and conditions: (a) NEt3, DCM, rt, 84%; (b) DHP, pyridinium p-tolu...
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Scheme 4: Coupling of linker 1 to different resins. Reactions and conditions: (a) 1. 1 and 16 or 17, Cs2CO3, ...
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Scheme 5: Model glycosylation by using an automated oligosaccharide synthesizer. Reactions and conditions: (a...
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Figure 2: Representative HPLC chromatograms of glycosylation experiments on PS-based and water-compatible res...
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Scheme 6: Glycosylation of 34 to linker 23 and subsequent Staudinger reduction of the azide. Reactions and co...
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- Published 14 Feb 2013
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Figure 1: Structure of some O-linked glycans found on the cell surface of P. aeruginosa.
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Scheme 1: Retrosynthetic analysis of D- and L-fucosamine building blocks.
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Scheme 2: (A) Synthesis of aldehydes 6a and 6b. (B) Alkyne reduction by hydrosilylation–protodesilylation seq...
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Scheme 3: Synthesis of D-fucosamine building blocks 8a and 8b.
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Scheme 4: Epimerization of aldehyde 6a.
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Scheme 5: Synthesis of L-fucosamine building block L-8a from D-Garner aldehyde.
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Scheme 6: Synthesis of D- and L-fucosamine-containing mono- and disaccharides carrying the pentanolamine link...
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