Safety-Catch and Multiply Cleavable Linkers in Solid- Phase Synthesis
نویسندگان
چکیده
This review article focuses on concepts that incorporate safety-catch and multiply cleavable linkers in solid-phase synthesis. Discussed are specific applications of such linkers in the synthesis of peptides, peptide mimetics, and “small” organic molecules, as well as their limitations for particular chemistries and reaction conditions. © 1999 John Wiley & Sons, Inc. Biopoly 47: 353–363, 1998
منابع مشابه
Acylsulfonamide 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 کاملFacile 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 کاملTopic : Safety - CAtch Linker ( SCAL )
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 ...
متن کاملThe "One-Bead-One-Compound" Combinatorial Library Method.
1. Peptoids 419 2. Oligocarbamates 420 3. Oligoureas 420 4. Vinylogous Sulfonyl Peptides 420 5. Peptidosulfonamides 420 6. Azatides 420 7. Ketides 420 D. Small Molecule Libraries 420 1. Acyclic Libraries 422 2. Libraries on Preformed Scaffolds 422 3. Heterocyclic Libraries 423 4. Structurally Heterogeneous Libraries 427 E. Cleavable Linkers 428 1. Single Cleavable Linkers 428 2. Multiply Cleava...
متن کاملN-acylsulfonamide linker activation by Pd-catalyzed allylation.
N-Acylsulfonamide safety-catch linkers are versatile tools in solid-phase organic synthesis because of their stability. This stability necessitates linker activation prior to compound cleavage. Here, we demonstrate that the N-acylsulfonamide group can react with a pi-allyl palladium complex and that these mild and neutral conditions can be exploited for linker activation. The advantages of this...
متن کامل