Topic : Safety - CAtch Linker ( SCAL )
نویسنده
چکیده
Definition: The term “safety catch principle” was introduced by Kenner in 1971 for peptide chemistry to describe a strategy that allows a linker to remain stable until it is activated for cleavage by a chemical modification. Currently, the term safety-catch is applied to a linker that is cleaved by performing two different reactions instead of the normal single step, that means that the linker is unreactive to the conditions of the library synthesis but may be activated by a simple chemical transformation to permit cleavage of the library from the solid phase to take place. Safety-catch linkers are used especially for solid-phase-syntheses, which are nowadays very important and can be used for nearly every known reaction (syntheses of alcohols, phenols, guanidines, aldehydes, carboxylic acids, amides, esters, ...).
منابع مشابه
Facile Synthesis of a Next Generation Safety‐Catch Acid‐Labile Linker, SCAL‐2, Suitable for Solid‐Phase Synthesis, On‐Support Display and for Post‐Synthesis Tagging
The SCAL linker, a safety catch linker, is amongst the most versatile linkers for solid phase synthesis. It was originally described in 1991 by Pátek and Lebl. Yet, its application has been hindered by the low yields of published synthetic routes. Over time, the exceptional versatility of this linker has been demonstrated in several applications of advanced solid phase synthesis of peptides and...
متن کاملAcylsulfonamide safety-catch linker: promise and limitations for solid–phase oligosaccharide synthesis
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.
متن کاملA Fluorous-Tagged “Safety Catch” Linker for Preparing Heterocycles by Ring-Closing Metathesis
A fluorous-tagged "safety catch" linker is described for the synthesis of heterocycles with use of ring-closing metathesis. The linker facilitates the purification of metathesis substrates, the removal of the catalyst, the functionalization of the products, and the release of only metathesis products. The synthesis of a range of heterocycles is described.
متن کاملAn oxidatively-activated safety catch linker for solid phase synthesis.
A N-benzyl-4-amino-2,2-dimethylbutanoic acid-based system has been developed as a new oxidatively activated safety catch linker for reaction monitoring and optimisation on solid support. The CAN promoted oxidative debenzylation of the tertiary N-benzylamine moiety, followed by concomitant cyclisation and release of alcohols and amines has been demonstrated both in solution phase model studies a...
متن کاملSafety-catch anchoring linkage for synthesis of peptide amides by Boc/Fmoc strategy
2-Methoxy-4,4’-bis(methylthio)benzhydrylamine (10) and the corresponding disulfoxide were prepared and tested as a model amide protecting groups for their stability toward acidic conditions. Subsequently, the novel 4-[4,4’-bis(methylsulfinyl)-2-o~-(9-fluorenylmethylo~c~bonyl) benzhydrylaminolbutanoic acid (SCAL) handle (9) has been prepared and applied to solid-phase peptide synthesis of C-term...
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