An Enzyme-Labile Safety Catch Linker for Combinatorial Synthesis on a Soluble Polymeric Support

Grether, Uwe; Waldmann, Herbert

doi:10.1002/(sici)1521-3773(20000502)39:9<1629::aid-anie1629>3.0.co;2-e

Cited by 41 publications

(12 citation statements)

References 4 publications

(8 reference statements)

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“…Self-Immolation by Cyclization Self-immolative spacers exploiting cyclization for their disassembly,i ncorporate linkers based on alkyl chains (Figure 3a,b), [15,[59][60][61][62][63] or on ortho mono-or disubstituted aromatic spacers (Figure 3c-e). [62,[64][65][66][67][68][69][70] Once activated, their disassembly involves anucleophilic attack on acarbonyl group (Figure 3a-d) or an electrophilic aliphatic carbon atom ( Figure 3e). [68] Thea ssociated cyclization occurs directly after activation or after apreliminary elimination step (Figure 3b).…”

Section: Methodsmentioning

confidence: 99%

Self‐Immolative Spacers: Kinetic Aspects, Structure–Property Relationships, and Applications

et al. 2015

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Self-immolative spacers are covalent assemblies tailored to correlate the cleavage of two chemical bonds after activation of a protective part in a precursor: Upon stimulation, the protective moiety is removed, which generates a cascade of disassembling reactions leading to the temporally sequential release of smaller molecules. Originally introduced to overcome limitations for drug delivery, self-immolative spacers have gained wide interest in medicinal chemistry, analytical chemistry, and material science. For most applications, the kinetics of the disassembly of the activated self-immolative spacer governs functional properties. This Review addresses kinetic aspects of self-immolation. It provides information for selecting a particular self-immolative motif for a specific demand. Moreover, it should help researchers design kinetic experiments and fully exploit the rich perspectives of self-immolative spacers.

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Section: Methodsmentioning

confidence: 99%

Self‐Immolative Spacers: Kinetic Aspects, Structure–Property Relationships, and Applications

et al. 2015

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“…Waldmann et al developed a second exo-linker following a new approach [37,38] which makes use of a safety-catch linker. It is based on the enzymatic cleavage of a functional group embodied in the linker.…”

Section: Endo-linkersmentioning

confidence: 99%

Biocatalysis in Polymer-Supported Synthesis: Enzyme-Labile Linker Groups

Reents¹,

Jeyaraj²,

Waldmann³

2001

Adv. Synth. Catal.

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“…As an alternative, the use of soluble polymers has been also explored as a solution to diffusion limitations 11, 12. The following paragraphs will discuss the advantages of the different approaches along with the technological drawbacks still waiting to be resolved.…”

Section: Supports For Solid Phase Biocatalysismentioning

confidence: 99%

“…A soluble functionalised PEG, called POE 600011, 46 (Rapp Polymere, Tübingen, Germany), was investigated by the group of Waldmann in the study of the PGA‐catalysed hydrolysis of an amide 12. The procedure for the production of POE 6000 polymer is quite similar to that already described for the PEGA resins (Scheme ) except for the use of a PEG monomer of higher molecular weight (MW = 6000).…”

Section: Supports For Solid Phase Biocatalysismentioning

confidence: 99%

“…Enzymatically‐cleavable linkers can match these requirements since enzymes work under very mild conditions (close to neutrality and room temperature) while offering high chemo‐, regio‐ and enantioselectivity. Enzymatically‐cleavable linkers for polymer‐supported synthesis have been extensively reviewed by Waldmann 12, 48…”

Section: Application Of Solid Phase Biocatalysismentioning

confidence: 99%

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Enhancement of the enzymatic digestibility of sugarcane bagasse by steam pretreatment impregnated with hydrogen peroxide

Rabelo

Rossell

Rocha

et al. 2012

Biotechnology Progress

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Sugarcane bagasse was subjected to steam pretreatment impregnated with hydrogen peroxide. Analyses were performed using 2(3) factorial designs and enzymatic hydrolysis was performed at two different solid concentrations and with washed and unwashed material to evaluate the importance of this step for obtaining high cellulose conversion. Similar cellulose conversion were obtained at different conditions of pretreatment and hydrolysis. When the cellulose was hydrolyzed using the pretreated material in the most severe conditions of the experimental design (210 °C, 15 min and 1.0% hydrogen peroxide), and using 2% (w/w) water-insoluble solids (WIS), and 15 FPU/g WIS, the cellulose conversion was 86.9%. In contrast, at a milder pretreatment condition (190 °C, 15 min and 0.2% hydrogen peroxide) and industrially more realistic conditions of hydrolysis (10% WIS and 10 FPU/g WIS), the cellulose conversion reached 82.2%. The step of washing the pretreated material was very important to obtain high concentrations of fermentable sugars.

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An Enzyme-Labile Safety Catch Linker for Combinatorial Synthesis on a Soluble Polymeric Support

Cited by 41 publications

References 4 publications

Self‐Immolative Spacers: Kinetic Aspects, Structure–Property Relationships, and Applications

Self‐Immolative Spacers: Kinetic Aspects, Structure–Property Relationships, and Applications

Biocatalysis in Polymer-Supported Synthesis: Enzyme-Labile Linker Groups

Enhancement of the enzymatic digestibility of sugarcane bagasse by steam pretreatment impregnated with hydrogen peroxide

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