A Practical Solid‐Phase Synthesis of Glycosylphosphatidylinositol Precursors

Reichardt, Niels‐Christian; Martín‐Lomas, Manuel

doi:10.1002/anie.200351950

Cited by 35 publications

(5 citation statements)

References 41 publications

(15 reference statements)

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“…This protecting group is mainly used in automated peptide synthesis but has also been used as an orthogonal protecting group in oligosaccharide synthesis. [17][18][19][20][21][22] Unfortunately, the reaction of unprotected glycopyranoses with FmocCl did not show high regioselectivity for the 6-position, as was achieved for 6-TBDMS protection in compound 2. There-Scheme 1.…”

Section: Development Of a Strategy For The Synthesis Of Cyclosal-(glymentioning

confidence: 99%

Synthesis of cycloSal‐(Glycopyranosyl‐6)‐phosphates as Activated Sugar Phosphates

2013

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The synthesis of cycloSal‐masked glycopyranosyl phosphates demands suitably protected precursors. A highly regioselective strategy for the preparation of cycloSal‐(1,2,3,4‐tetra‐O‐acetylglycopyranosyl‐6)‐phosphates was developed. Intermediate introduction of the Fmoc‐group allowed the isolation of the 1,2,3,4‐tetra‐O‐acetyl glycopyranoses to be skipped, thus, no isomerization occurred. Glycopyranoses were first converted into the 6‐O‐TBDMS‐1,2,3,4‐tetra‐O‐acetyl derivatives then, in a one‐pot reaction, the silyl ether was cleaved and the resulting 1,2,3,4‐tetra‐O‐acetyl glycopyranoses were trapped with Fmoc‐chloride. In this exchange of protecting groups no acetyl group migration occurred. The 6‐O‐Fmoc‐protected intermediates were selectively converted into the cycloSal‐masked glycopyranosyl phosphates in a one‐pot reaction. Finally, the reactivity of these activated glycopyranosyl‐6‐phosphates was demonstrated in the synthesis of 1,6‐diglycopyranosyl‐phosphates.

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Section: Development Of a Strategy For The Synthesis Of Cyclosal-(glymentioning

confidence: 99%

Synthesis of cycloSal‐(Glycopyranosyl‐6)‐phosphates as Activated Sugar Phosphates

2013

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“…We have already developed a step by step solid-phase synthesis of GPI anchor precursors which may allow for the synthesis of a variety of pseudotrisaccharide structures. 39 In this synthetic approach, the common precursor 52 was transformed in three steps into diol 88 which was attached to a functionalised resin through OH-1 of the myo-inositol unit. We also explored a different approach however, starting from alcohol 57 and attaching the pseudodisaccharide building block to the solid-support through 6-OH of the 2-azido-2-deoxy-a-Dglucopyranosyl moiety.…”

Section: Synthesismentioning

confidence: 99%

Design and synthesis of inositolphosphoglycan putative insulin mediators

et al. 2005

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The binding modes of a series of molecules, containing the glucosamine (1-->6) myo-inositol structural motif, into the ATP binding site of the catalytic subunit of cAMP-dependent protein kinase (PKA) have been analysed using molecular docking. These calculations predict that the presence of a phosphate group at the non-reducing end in pseudodisaccharide and pseudotrisaccharide structures properly orientate the molecule into the binding site and that pseudotrisaccharide structures present the best shape complementarity. Therefore, pseudodisaccharides and pseudotrisaccharides have been synthesised from common intermediates using effective synthetic strategies. On the basis of this synthetic chemistry, the feasibility of constructing small pseudotrisaccharide libraries on solid-phase using the same intermediates has been explored. The results from the biological evaluation of these molecules provide additional support to an insulin-mediated signalling system which involves the intermediacy of inositolphosphoglycans as putative insulin mediators.

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“…The tetrasaccharide was then linked to the pseudodisaccharide in solution to afford the GPI core in 32% yield. In a recent report on the solid-phase synthesis of the GPI core 70 by Reichardt and Martin-Lomas [51] (Scheme 9), the pseudodisaccharide was prepared first in solution and was then attached to a polyethylene glycol (PEG)-grafted polystyrene resin. This approach was employed to avoid solidphase formation of the most problematic glycosidic linkage and to facilitate the final-stage purification.…”

Section: Scheme 7 Highly Convergent Synthesis Of the Intact Gpi Of Tmentioning

confidence: 99%

Chemical Synthesis of GPIs and GPI‐Anchored Glycopeptides

Guo

Bishop

2004

Eur J Org Chem

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This microreview summarizes some recent progress in the study of glycosylphosphatidylinositols (GPI), focusing on the strategies established for the synthesis of optically pure myoinositol derivatives and complex GPIs and GPI conjugates. Although in the past decade many GPIs have been achieved by linear, convergent and solid-phase synthesis, the GPIs with 2-O-acylated inositol residues and the GPI conjugates of peptides and glycopeptides have not been accomplished

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A Practical Solid‐Phase Synthesis of Glycosylphosphatidylinositol Precursors

Cited by 35 publications

References 41 publications

Synthesis of cycloSal‐(Glycopyranosyl‐6)‐phosphates as Activated Sugar Phosphates

Synthesis of cycloSal‐(Glycopyranosyl‐6)‐phosphates as Activated Sugar Phosphates

Design and synthesis of inositolphosphoglycan putative insulin mediators

Chemical Synthesis of GPIs and GPI‐Anchored Glycopeptides

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