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T1 - Linker Strategies in Solid-Phase Organic Synthesis

N2 - Solid-phase peptide synthesis, head-to-tail cyclization, and subsequent radiolabeling provided a reproducible, simple, rapid synthetic method to generate the cyclic peptide radiotracer cRGDyK([18F]FBA). Herein is reported the first on-resin cyclization and 18F-radiolabeling of a cyclic peptide (cRGDyK) in an overall peptide synthesis yield of 88% (cRGDyK(NH2)) and subsequent radiolabeling yield of 14 ± 2% (decay corrected, n = 4). This approach is generally applicable to the development of an automated process for the synthesis of cyclic radiolabeled peptides for positron emission tomography (PET).

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 synthesis and fluorine-18 radiolabeling of cycloRGDyK

BT - Linker Strategies in Solid-Phase Organic Synthesis

Aziridines in Parallel- and Solid-Phase Synthesis.

Using the Fmoc protection strategy of solid phase peptide synthesis, a 10 amino acid peptide was prepared and cyclized in a "head-to-tail" fashion while it was attached to the solid support. Cyclization was accomplished with either BOP or carbodiimide and the peptide was cleaved from the resin and purified using standard protocols.

N2 - Using the Fmoc protection strategy of solid phase peptide synthesis, a 10 amino acid peptide was prepared and cyclized in a "head-to-tail" fashion while it was attached to the solid support. Cyclization was accomplished with either BOP or carbodiimide and the peptide was cleaved from the resin and purified using standard protocols.

Advances in Solid-Phase Cycloadditions for Heterocyclic Synthesis.

AB - Using the Fmoc protection strategy of solid phase peptide synthesis, a 10 amino acid peptide was prepared and cyclized in a "head-to-tail" fashion while it was attached to the solid support. Cyclization was accomplished with either BOP or carbodiimide and the peptide was cleaved from the resin and purified using standard protocols.

Solid-phase peptide synthesis, head-to-tail cyclization, and subsequent radiolabeling provided a reproducible, simple, rapid synthetic method to generate the cyclic peptide radiotracer cRGDyK([18F]FBA). Herein is reported the first on-resin cyclization and 18F-radiolabeling of a cyclic peptide (cRGDyK) in an overall peptide synthesis yield of 88% (cRGDyK(NH2)) and subsequent radiolabeling yield of 14 ± 2% (decay corrected, n = 4). This approach is generally applicable to the development of an automated process for the synthesis of cyclic radiolabeled peptides for positron emission tomography (PET).

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M., Solid-phase synthesis of C-terminally modified peptides.


L., The Convergence of Synthetic Organic and Polymer Chemistries.

AB - Solid-phase peptide synthesis, head-to-tail cyclization, and subsequent radiolabeling provided a reproducible, simple, rapid synthetic method to generate the cyclic peptide radiotracer cRGDyK([18F]FBA). Herein is reported the first on-resin cyclization and 18F-radiolabeling of a cyclic peptide (cRGDyK) in an overall peptide synthesis yield of 88% (cRGDyK(NH2)) and subsequent radiolabeling yield of 14 ± 2% (decay corrected, n = 4). This approach is generally applicable to the development of an automated process for the synthesis of cyclic radiolabeled peptides for positron emission tomography (PET).

Clean Chemical Synthesis in Water - Organic chemistry

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.

Why is solid phase peptide synthesis limited to 70 …

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.

Solid Phase Peptide Synthesis : The Basics - YouTube

Preparation, Characterization, and Application of Poly(vinyl alcohol)-graft-Poly(ethylene glycol) Resins: Novel Polymer Matrices for Solid-Phase Synthesis.

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