Linker Strategies in Solid-Phase Organic Synthesis guides the ..

AB - Linker design is an expanding field with an exciting future in state-of-the-art organic synthesis. Ever-increasing numbers of ambitious solution phase reactions are being adapted for solid-phase organic chemistry and to accommodate them, large numbers of sophisticated linker units have been developed and are now routinely employed in solid-phase synthesis. Linker Strategies in Solid-Phase Organic Synthesis guides the reader through the evolution of linker units from their genesis in solid-supported peptide chemistry to the cutting edge diversity linker units that are defining a new era of solid phase synthesis. Individual linker classes are covered in easy to follow chapters written by international experts in their respective fields and offer a comprehensive guide to linker technology whilst simultaneously serving as a handbook of synthetic transformations now possible on solid supports. Topics include: The principles of solid phase organic synthesis. Electrophile and nucleophile cleavable linker units. Cyclative cleavage as a solid phase strategy. Photocleavable linker units. Safety-catch linker units. Enzyme cleavable linker units. T1 and T2 -versatile triazene linker groups. Hydrazone linker units. Benzotriazole linker units. Phosphorus linker units. Sulfur linker units. Selenium and tellurium linker units. Sulfur, oxygen and selenium linker units cleaved by radical processes. Silicon and germanium linker units. Boron and stannane linker units. Bismuth linker units. Transition metal carbonyl linker units. Linkers releasing olefins or cycloolefins by ring-closing metathesis. Fluorous linker units. Solid-phase radiochemistry. The book concludes with extensive linker selection tables, cataloguing the linker units described in this book according to the substrate liberated upon cleavage and conditions used to achieve such cleavage, enabling readers to choose the right linker unit for their synthesis. Linker Strategies in Solid-Phase Organic Synthesis is an essential guide to the diversity of linker units for organic chemists in academia and industry working in the broad areas of solid-phase organic synthesis and diversity oriented synthesis, medicinal chemists in the pharmaceutical industry who routinely employ solid-phase chemistry in the drug discovery business, and advanced undergraduates, postgraduates, and organic chemists with an interest in leading-edge developments in their field.

T1 - Solid-phase total synthesis of cyclic peptide brachystemin A and its immunomodulating activity

Based on these unexpected findings, we hypothesized that excess glycosylating agent may alkylate the sulfamyl group during glycosylation, such that subsequent cleavage provides products 20 and 21. To test this, the amount of glycosylating agent was decreased during a reaction, which resulted in the production of glycosylated linkers 21 and 22. It was evident that two unexpected reactions had occurred. First, the use of excess glycosylating agent, common practice for solid-phase-synthesis protocols, leads to activation of the sulfamyl group of the acylsulfonamide safety-catch linker, permitting cleavage at this location. This reaction had not been reported previously [–], because the architecture of this safety-catch linker means that the modified sulfamyl group remains on the resin after cleavage and release of the product, and this was not examined. As the new bifunctional resins 11 and 16 contain the additional Zemplén cleavage site, the product of this dominant but undesired reaction was evident. Second, the observation that reducing the concentration of the glycosylation agent caused an increase in the production of glycosylated linker 21, implied that sodium methoxide may directly cleave safety-catch linkers without prior activation.


Carboxylic Acid Linkers - Solid Phase Synthesis

A new safety-catch linker for solid-phase organic synthesis is described

Safety-catch linkers are useful for solid-phase oligosaccharide synthesis as they are orthogonal to many common protective groups. A new acylsulfonamide safety-catch linker was designed, synthesized and employed during glycosylations using an automated carbohydrate synthesizer. The analysis of the cleavage products revealed shortcomings for oligosaccharide synthesis.


A linker for solid phase synthesis of nucleic acid, ..

Linker design is an expanding field with an exciting future in state-of-the-art organic synthesis. Ever-increasing numbers of ambitious solution phase reactions are being adapted for solid-phase organic chemistry and to accommodate them, large numbers of sophisticated linker units have been developed and are now routinely employed in solid-phase synthesis. Linker Strategies in Solid-Phase Organic Synthesis guides the reader through the evolution of linker units from their genesis in solid-supported peptide chemistry to the cutting edge diversity linker units that are defining a new era of solid phase synthesis. Individual linker classes are covered in easy to follow chapters written by international experts in their respective fields and offer a comprehensive guide to linker technology whilst simultaneously serving as a handbook of synthetic transformations now possible on solid supports. Topics include: The principles of solid phase organic synthesis. Electrophile and nucleophile cleavable linker units. Cyclative cleavage as a solid phase strategy. Photocleavable linker units. Safety-catch linker units. Enzyme cleavable linker units. T1 and T2 -versatile triazene linker groups. Hydrazone linker units. Benzotriazole linker units. Phosphorus linker units. Sulfur linker units. Selenium and tellurium linker units. Sulfur, oxygen and selenium linker units cleaved by radical processes. Silicon and germanium linker units. Boron and stannane linker units. Bismuth linker units. Transition metal carbonyl linker units. Linkers releasing olefins or cycloolefins by ring-closing metathesis. Fluorous linker units. Solid-phase radiochemistry. The book concludes with extensive linker selection tables, cataloguing the linker units described in this book according to the substrate liberated upon cleavage and conditions used to achieve such cleavage, enabling readers to choose the right linker unit for their synthesis. Linker Strategies in Solid-Phase Organic Synthesis is an essential guide to the diversity of linker units for organic chemists in academia and industry working in the broad areas of solid-phase organic synthesis and diversity oriented synthesis, medicinal chemists in the pharmaceutical industry who routinely employ solid-phase chemistry in the drug discovery business, and advanced undergraduates, postgraduates, and organic chemists with an interest in leading-edge developments in their field.

Solid phase organic synthesis is ..

N2 - Linker design is an expanding field with an exciting future in state-of-the-art organic synthesis. Ever-increasing numbers of ambitious solution phase reactions are being adapted for solid-phase organic chemistry and to accommodate them, large numbers of sophisticated linker units have been developed and are now routinely employed in solid-phase synthesis. Linker Strategies in Solid-Phase Organic Synthesis guides the reader through the evolution of linker units from their genesis in solid-supported peptide chemistry to the cutting edge diversity linker units that are defining a new era of solid phase synthesis. Individual linker classes are covered in easy to follow chapters written by international experts in their respective fields and offer a comprehensive guide to linker technology whilst simultaneously serving as a handbook of synthetic transformations now possible on solid supports. Topics include: The principles of solid phase organic synthesis. Electrophile and nucleophile cleavable linker units. Cyclative cleavage as a solid phase strategy. Photocleavable linker units. Safety-catch linker units. Enzyme cleavable linker units. T1 and T2 -versatile triazene linker groups. Hydrazone linker units. Benzotriazole linker units. Phosphorus linker units. Sulfur linker units. Selenium and tellurium linker units. Sulfur, oxygen and selenium linker units cleaved by radical processes. Silicon and germanium linker units. Boron and stannane linker units. Bismuth linker units. Transition metal carbonyl linker units. Linkers releasing olefins or cycloolefins by ring-closing metathesis. Fluorous linker units. Solid-phase radiochemistry. The book concludes with extensive linker selection tables, cataloguing the linker units described in this book according to the substrate liberated upon cleavage and conditions used to achieve such cleavage, enabling readers to choose the right linker unit for their synthesis. Linker Strategies in Solid-Phase Organic Synthesis is an essential guide to the diversity of linker units for organic chemists in academia and industry working in the broad areas of solid-phase organic synthesis and diversity oriented synthesis, medicinal chemists in the pharmaceutical industry who routinely employ solid-phase chemistry in the drug discovery business, and advanced undergraduates, postgraduates, and organic chemists with an interest in leading-edge developments in their field.