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2 article(s) from Collot, Mayeul

Glycosylation efficiencies on different solid supports using a hydrogenolysis-labile linker

Mayeul Collot,
Steffen Eller,
Markus Weishaupt and
Peter H. Seeberger

Beilstein J. Org. Chem. 2013, 9, 97–105, doi:10.3762/bjoc.9.13

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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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Letter

Published 16 Jan 2013

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Acylsulfonamide safety-catch linker: promise and limitations for solid–phase oligosaccharide synthesis

Jian Yin,
Steffen Eller,
Mayeul Collot and
Peter H. Seeberger

Beilstein J. Org. Chem. 2012, 8, 2067–2071, doi:10.3762/bjoc.8.232

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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 26 Nov 2012

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