Tuning the Product Spectrum of a Glycoside Hydrolase Enzyme by a Combination of Site‐Directed Mutagenesis and Tyrosine‐Specific Chemical Modification

Ertl, Julia; Ortiz-Soto, María Elena; Le, Thien Anh; Bechold, Julian; Shan, Junwen; Teßmar, Jörg; Engels, Bernd; Seibel, Jürgen

doi:10.1002/chem.201900576

Cited by 15 publications

(14 citation statements)

References 38 publications

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“…As is known, cellulose synthase can produce cellulose fibers in plants and bacteria. The extracellular levansucrase can catalyze sucrose to levan. , These valuable approaches can be used to establish clear structure–property relationships on the basis of the pure glycans.…”

Section: Novel Synthetic Approaches To Polysaccharide Mimics and Glyc...mentioning

confidence: 99%

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Synthesis and Biopharmaceutical Applications of Sugar-Based Polymers: New Advances and Future Prospects

Wang

Zhang

et al. 2021

ACS Biomater. Sci. Eng.

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The rapid rise in research interest in carbohydrate-based polymers is undoubtedly due to the nontoxic nature of such materials in an in vivo environment and the versatile roles that the polymers can play in cellular functions. Such polymers have served as therapeutic tools for drug delivery, including antigens, proteins, and genes, as well as diagnostic devices. Our focus in the first half of this Review is on synthetic methods based on ring-opening polymerization and enzyme-catalyzed polymerization, along with controlled radical polymerization. In the second half of this Review, sugar-based polymers are discussed on the basis of their remarkable success in competitive receptor binding, as multifunctional nanocarriers of targeting inhibitors for cancer treatment, in genome-editing delivery, in immunotherapy based on endogenous antibody recruitment, and in treatment of respiratory diseases, including influenza A. Particular emphasis is put on the synthesis and biopharmaceutical applications of sugar-based polymers published in the most recent 5 years. A noticeable attribute of carbohydrate-based polymers is that the sugar–receptor interactions can be facilitated by the cooperative effect of multiple sugar units. Their diversified topology and structures will drive the development of new synthetic strategies and bring about important applications, including coronavirus-related drug therapy.

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Section: Novel Synthetic Approaches To Polysaccharide Mimics and Glyc...mentioning

confidence: 99%

“…The extracellular levansucrase can catalyze sucrose to levan. 53,54 These valuable approaches can be used to establish clear structure−property relationships on the basis of the pure glycans.…”

Section: Novel Synthetic Approaches Tomentioning

confidence: 99%

Synthesis and Biopharmaceutical Applications of Sugar-Based Polymers: New Advances and Future Prospects

Wang

Zhang

et al. 2021

ACS Biomater. Sci. Eng.

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“…1). 37,[39][40][41][42][43] NMePhUr and NMeLum were activated using ruthenium photocatalysts, 44 hemin and H2O2, 40 enzymatic systems (horseradish peroxidase and H2O2, laccase) 37,39,45 and electrochemically. 43 In the present study, we aimed to evaluate and compare the relative efficiency of new and previously reported urazoles and luminols derivatives in the electrochemical-tyrosine-click labelling strategy (Fig.…”

Section: Introductionmentioning

confidence: 99%

Luminol anchors improve the electrochemical-tyrosine-click labelling of proteins

et al. 2021

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“…1). 36,[38][39][40][41][42] NMePhUr and NMeLum were activated using ruthenium photocatalysts, 43 hemin and H2O2, 39 enzymatic systems (horseradish peroxidase and H2O2, laccase) 36,38,44 and electrochemically. 42 In this work, we aimed to evaluate and compare the relative efficiency of new or previously reported urazoles and luminols derivatives in the electrochemical-click labelling strategy (Fig.…”

Section: Introductionmentioning

confidence: 99%

Luminol Anchors Improve the Electrochemical-Tyrosine-Click Labelling of Proteins

Depienne

Álvarez-Dorta

Croyal

et al. 2021

Preprint

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New methodologies for the chemo-selective modifications of peptides and native proteins are of great importance in chemical biology and for the developm ent of therapeutic conjugates. Less abundant and uncharged amino-acid residues are interesting targets to form less heterogeneous conjugates and preserve biological functions. Phenylurazole (PhUr), Nmethylphenylurazole (NMePhUr) and N-methylluminol (NMeLum) derivatives were described as tyrosine (Y) anchors after chemical or enzymatic oxydations. Recently, we developed the first electrochemical Y-bioconjugation method coined eYclick to activate PhUr in biocompatible media. In this work, we assessed the limitations, benefits and relative efficiencies of eY-click conjugations performed with a set of PhUr, NMePhUr and NMeLum derivatives. Results evidenced a high efficiency of NMeLum that showed a complete Y-chemoselectivity on polypeptides and biologically relevant proteins after soft electrochemical activation. Side reactions on nucleophilic or heteroaromatic amino-acids such as lysine or tryptophan were never observed during mass spectrometry analysis. Myoglobine, bovine serum albumin, a plant mannosidase, glucose oxidase and the therapeutically relevant antibody trastuzumab were efficiently labelled with a fluorescent probe in a twostep approach combining eY-click and strain-promoted azide-alkyne cyclization (SPAAC). The proteins conserved their structural integrity as observed by circular dichroism and the trastuzumab conjugate showed a similar binding affinity for the natural HER2 ligand as shown by bio-layer interferometry. Compared to our previously described protocol with PhUr, eY-click with NMeLum species showed faster reaction kinetics, higher (complete) Y-chemoselectivity and reactivity, and offer the interesting possibility for the double tagging of solvent-exposed Y.

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Tuning the Product Spectrum of a Glycoside Hydrolase Enzyme by a Combination of Site‐Directed Mutagenesis and Tyrosine‐Specific Chemical Modification

Cited by 15 publications

References 38 publications

Synthesis and Biopharmaceutical Applications of Sugar-Based Polymers: New Advances and Future Prospects

Synthesis and Biopharmaceutical Applications of Sugar-Based Polymers: New Advances and Future Prospects

Luminol anchors improve the electrochemical-tyrosine-click labelling of proteins

Luminol Anchors Improve the Electrochemical-Tyrosine-Click Labelling of Proteins

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