Enzyme-cleavable linkers for peptide and glycopeptide synthesis

Maltman, Beatrice A.; Bejugam, Mallesham; Flitsch, Sabine L.

doi:10.1039/b506154g

Cited by 18 publications

(14 citation statements)

References 21 publications

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“…[23,24] Detailed analysis of such reactions was troublesome because of the need for cleavable linkers, which were in some cases also labile in the presence of proteases. [25] The SAM platform proved to be much more successful (Figure 1 D). Thus, phenylalanine and leucine were immobilised on the SAM array as described before, and were incubated with a mixture of thermolysin and a saturated solution of either FmocGly, FmocPhe, FmocLeu or FmocAla.…”

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confidence: 94%

SPOT Synthesis of Peptide Arrays on Self‐Assembled Monolayers and their Evaluation as Enzyme Substrates

et al. 2008

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confidence: 94%

SPOT Synthesis of Peptide Arrays on Self‐Assembled Monolayers and their Evaluation as Enzyme Substrates

et al. 2008

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“…The substrates were attached via a linker containing L-phenylalanine (L-Phe) that enabled hydrolytic release of the reaction products from the solid support by α-chymotrypsin (CT) under ambient conditions. CT-catalyzed cleavage allows mild hydrolysis of typically recalcitrant amide-based linkers [11, 17] . Such a strategy was desirable to enable structural preservation of compounds that might be unstable during acid or base cleavage [8a] .…”

Section: Resultsmentioning

confidence: 99%

Expanding the Scope of Biocatalysis: Oxidative Biotransformations on Solid‐Supported Substrates

Brooks¹,

Coulombel²,

Ahuja³

et al. 2008

Adv Synth Catal

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Oxidative biocatalytic reactions were performed on solid-supported substrates, thus expanding the repertoire of biotransformations that can be carried out on the solid phase. Various phenylacetic and benzoic acid analogs were attached to controlled pore glass beads via an enzyme-cleavable linker. Reactions catalyzed by peroxidases (soybean and chloro), tyrosinase, and alcohol oxidase/dehydrogenase gave a range of products, including oligophenols, halogenated aromatics, catechols, and aryl aldehydes. The resulting products were recovered following cleavage from the beads using α-chymotrypsin to selectively hydrolyze a chemically non-labile amide linkage. Controlled pore glass (CPG) modified with a polyethylene glycol (PEG) linker afforded substantially higher product yields than non-PEGylated CPG or non-swellable polymeric resins. This work represents the first attempt to combine solid-phase oxidative biotransformations with subsequent protease-catalyzed cleavage, and serves to further expand the use of biocatalysis in synthetic and medicinal chemistry.

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“…Recently, α‐chymotrypsin was reported to be able to cleave ester linkers commonly used in solid phase peptide, such as Wang linker, HMBA and HOA, leading to the release of a range of structurally variable peptides 58. Also, the HMPA linker was efficiently cleaved by chymotrypsin and this finding has been applied to peptide and glycopeptide59 synthesis, as shown in Table 3.…”

Section: Application Of Solid Phase Biocatalysismentioning

confidence: 99%

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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Enzyme-cleavable linkers for peptide and glycopeptide synthesis

Cited by 18 publications

References 21 publications

SPOT Synthesis of Peptide Arrays on Self‐Assembled Monolayers and their Evaluation as Enzyme Substrates

SPOT Synthesis of Peptide Arrays on Self‐Assembled Monolayers and their Evaluation as Enzyme Substrates

Expanding the Scope of Biocatalysis: Oxidative Biotransformations on Solid‐Supported Substrates

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

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