Synthesis of deoxy and alanine-substituted derivatives of a T cell stimulating glycopeptide—An investigation of conditions for cleavage from the solid phase and deprotection

Sjölin, Petter; George, Shaji K.; Bergquist, Karl‐Erik; Roy, Somnath; Svensson, Åsa; Kihlberg, Jan

doi:10.1039/a900435a

Cited by 22 publications

(44 citation statements)

References 35 publications

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“…30 Complete cleavage required use of TFA and cationic scavengers, 31 as commonly used in peptide synthesis, but at elevated temperature. To explore conditions for cleavage of the fluorinated linker 14 versus the corresponding nonfluorinated linker, resin-bound 15a and 15b were prepared and subjected to cleavage under different conditions ( Figure 1).…”

Section: Resultsmentioning

confidence: 99%

Preparation of Fluorinated Linkers: Use of ¹⁹F NMR Spectroscopy to Establish Conditions for Solid-Phase Synthesis of Pilicide Libraries

2000

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Three fluorinated linkers which are analogues of linkers commonly used in solid-phase peptide synthesis have been prepared. One of the linkers was used in combination with gel-phase 19F NMR spectroscopy to develop conditions for solid-phase synthesis of two libraries of pilicides, i.e. compounds designed to inhibit assembly of adhesive pili in uropathogenic Escherichia coli. Attachment to and cleavage from the linker could be monitored based on the chemical shift of the fluorine atom of the linker. In addition, use of the linker as internal standard allowed quantification and optimization of reactions occurring further away from the linker when fluorinated building blocks were employed. Importantly, high-quality 19F NMR spectra were obtained for compounds linked to a TentaGel resin in a standard NMR tube using an ordinary NMR instrument.

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Section: Resultsmentioning

confidence: 99%

Preparation of Fluorinated Linkers: Use of ¹⁹F NMR Spectroscopy to Establish Conditions for Solid-Phase Synthesis of Pilicide Libraries

2000

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“…We used serine as amolecular platform flanked by one lipophilic tail linked to the amino group with asaccharide group grafted onto the hydroxy moiety,and two carboxylates derived from glutamic acid were attached to the carboxylic acid of serine.D irect glycosylation at the hydroxy group of serine was hampered by a b-elimination reaction, as already reported. [20,21] We achieved the synthesis through the introduction of apropargyl moiety on N-Boc serine,coupling with glutamic acid esters,and click chemistry with either protected glucosyl or maltosyl groups bearing an azido group,followed by deprotection of the benzyl and acetate groups.W e prepared compounds with either as hort (8c, 8d), medium (8b, 9b), or long aliphatic tail (8a, 9a). We also introduced branched chains (8e, 8f)a nd chains bearing ah ydrophobic cyclic ring (8g).…”

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confidence: 99%

Glycosyl‐Substituted Dicarboxylates as Detergents for the Extraction, Overstabilization, and Crystallization of Membrane Proteins

et al. 2018

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To tackle the problems associated with membrane protein (MP) instability in detergent solutions, we designed a series of glycosyl-substituted dicarboxylate detergents (DCODs) in which we optimized the polar head to clamp the membrane domain by including, on one side, two carboxyl groups that form salt bridges with basic residues abundant at the membrane-cytoplasm interface of MPs and, on the other side, a sugar to form hydrogen bonds. Upon extraction, the DCODs 8 b, 8 c, and 9 b preserved the ATPase function of BmrA, an ATP-binding cassette pump, much more efficiently than reference or recently designed detergents. The DCODs 8 a, 8 b, 8 f, 9 a, and 9 b induced thermal shifts of 20 to 29 °C for BmrA and of 13 to 21 °C for the native version of the G-protein-coupled adenosine receptor A R. Compounds 8 f and 8 g improved the diffraction resolution of BmrA crystals from 6 to 4 Å. DCODs are therefore considered to be promising and powerful tools for the structural biology of MPs.

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“…Thus, known 2,3,4-tri-O-acetyl-D-fucopyranose (20) [27] was converted into the corresponding p-methoxyphenyl glycoside (21) in 78% yield. De-O-acetylation followed by 3,4-O-isopropylidene acetal formation using 2,2-dimethoxy-propane and 10-camphorsulfonic acid in dry acetone afforded the required acceptor 22 in 87% overall yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of a tetra- and a trisaccharide related to an anti-tumor saponin “Julibroside J28” from Albizia julibrissin

Roy

Mukhopadhyay

2007

Glycoconj J

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Simple and convergent synthesis of a tetra- and a trisaccharide portions of an antitumor compound Julibroside J(28), isolated from Albizia julibrissin, that showed significant in vitro antitumor activity against HeLa, Bel-7402 and PC-3M-1E8 cancer cell lines is reported. The tetrasaccharide has been synthesized as its p-methoxyphenyl glycoside starting from commercially available D-glucose, L-rhamnose and L-arabinose. The trisaccharide part has been synthesized from commercially available N-acetyl D-glucosamine, D-fucose and D-xylose using simple protecting group manipulations. Sulfuric acid immobilized on silica has been used successfully as a Brönsted acid catalyst for the crucial glycosylation steps.

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Synthesis of deoxy and alanine-substituted derivatives of a T cell stimulating glycopeptide—An investigation of conditions for cleavage from the solid phase and deprotection

Cited by 22 publications

References 35 publications

Preparation of Fluorinated Linkers: Use of ¹⁹F NMR Spectroscopy to Establish Conditions for Solid-Phase Synthesis of Pilicide Libraries

Preparation of Fluorinated Linkers: Use of ¹⁹F NMR Spectroscopy to Establish Conditions for Solid-Phase Synthesis of Pilicide Libraries

Glycosyl‐Substituted Dicarboxylates as Detergents for the Extraction, Overstabilization, and Crystallization of Membrane Proteins

Synthesis of a tetra- and a trisaccharide related to an anti-tumor saponin “Julibroside J28” from Albizia julibrissin

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Synthesis of deoxy and alanine-substituted derivatives of a T cell stimulating glycopeptide—An investigation of conditions for cleavage from the solid phase and deprotection

Cited by 22 publications

References 35 publications

Preparation of Fluorinated Linkers: Use of 19F NMR Spectroscopy to Establish Conditions for Solid-Phase Synthesis of Pilicide Libraries

Preparation of Fluorinated Linkers: Use of 19F NMR Spectroscopy to Establish Conditions for Solid-Phase Synthesis of Pilicide Libraries

Glycosyl‐Substituted Dicarboxylates as Detergents for the Extraction, Overstabilization, and Crystallization of Membrane Proteins

Synthesis of a tetra- and a trisaccharide related to an anti-tumor saponin “Julibroside J28” from Albizia julibrissin

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Preparation of Fluorinated Linkers: Use of ¹⁹F NMR Spectroscopy to Establish Conditions for Solid-Phase Synthesis of Pilicide Libraries

Preparation of Fluorinated Linkers: Use of ¹⁹F NMR Spectroscopy to Establish Conditions for Solid-Phase Synthesis of Pilicide Libraries