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      Product-oriented chemical surface modification of a levansucrase (SacB) via an ene-type reaction†

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          Abstract

          A flexible tyrosine-attached chemical lid prevents premature disengagement of growing oligosaccharides and triggers the synthesis of a high molecular weight polymer.

          Abstract

          Carbohydrate processing enzymes are sophisticated tools of living systems that have evolved to execute specific reactions on sugars. Here we present for the first time the site-selective chemical modification of exposed tyrosine residues in SacB, a levansucrase from Bacillus megaterium ( Bm-LS) for enzyme engineering purposes via an ene-type reaction. Bm-LS is unable to sustain the synthesis of high molecular weight (HMW) levan (a fructose polymer) due to protein–oligosaccharide dissociation events occurring at an early stage during polymer elongation. We switched the catalyst from levan-like oligosaccharide synthesis to the efficient production of a HMW fructan polymer through the covalent addition of a flexible chemical side-chain that fluctuates over the central binding cavity of the enzyme preventing premature oligosaccharide disengagement.

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          Selective chemical protein modification.

          Christopher D. Spicer, Benjamin G. Davis (2014)
          Chemical modification of proteins is an important tool for probing natural systems, creating therapeutic conjugates and generating novel protein constructs. Site-selective reactions require exquisite control over both chemo- and regioselectivity, under ambient, aqueous conditions. There are now various methods for achieving selective modification of both natural and unnatural amino acids--each with merits and limitations--providing a 'toolkit' that until 20 years ago was largely limited to reactions at nucleophilic cysteine and lysine residues. If applied in a biologically benign manner, this chemistry could form the basis of true Synthetic Biology.
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            Biocatalysis in organic chemistry and biotechnology: past, present, and future.

            Manfred Reetz (2013)
            Enzymes as catalysts in synthetic organic chemistry gained importance in the latter half of the 20th century, but nevertheless suffered from two major limitations. First, many enzymes were not accessible in large enough quantities for practical applications. The advent of recombinant DNA technology changed this dramatically in the late 1970s. Second, many enzymes showed a narrow substrate scope, often poor stereo- and/or regioselectivity and/or insufficient stability under operating conditions. With the development of directed evolution beginning in the 1990s and continuing to the present day, all of these problems can be addressed and generally solved. The present Perspective focuses on these and other developments which have popularized enzymes as part of the toolkit of synthetic organic chemists and biotechnologists. Included is a discussion of the scope and limitation of cascade reactions using enzyme mixtures in vitro and of metabolic engineering of pathways in cells as factories for the production of simple compounds such as biofuels and complex natural products. Future trends and problems are also highlighted, as is the discussion concerning biocatalysis versus nonbiological catalysis in synthetic organic chemistry. This Perspective does not constitute a comprehensive review, and therefore the author apologizes to those researchers whose work is not specifically treated here.
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              Click chemistry generates privileged CH hydrogen-bonding triazoles: the latest addition to anion supramolecular chemistry.

              H Flood, F Y Hua (2010)
              The supramolecular chemistry of anions provides a means to sense and manipulate anions in their many chemical and biological roles. For this purpose, Click chemistry facilitated the synthetic creation of new receptors and thus, an opportunity to aid in the recent re-examination of CH...anion hydrogen bonding. This tutorial review will focus on the privileged C-H hydrogen bond donor of the 1,2,3-triazole ring systems as elucidated from anion-binding studies with macrocyclic triazolophanes and other receptors. Triazolophanes are shape-persistent and planar macrocycles that direct four triazole and four phenylene CH groups into a 3.7 A cavity. They display strong (log K(Cl(-)) = 7), size-dependent halide binding (Cl(-) > Br(-) > F(-) > I(-)) and a rich set of binding equilibria. For instance, the too large iodide (4.4 A) can be sandwiched between two pyridyl-based triazolophanes with extreme positive cooperativity. Computational studies verify the triazole's hydrogen bond strength indicating it approaches the traditional NH donors from pyrrole. These examples, those of transport, sensing (e.g., ion-selective electrodes), templation, and versatile synthesis herald the use of triazoles in anion-receptor chemistry.
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                Author and article information

                Journal
                Journal ID (nlm-ta): Chem Sci
                Journal ID (iso-abbrev): Chem Sci
                Title: Chemical Science
                Publisher: Royal Society of Chemistry
                ISSN (Print): 2041-6520
                ISSN (Electronic): 2041-6539
                Publication date (Electronic): 22 May 2018
                Publication date Collection: 28 June 2018
                Volume: 9
                Issue: 24
                Pages: 5312-5321
                Affiliations
                [a ] Institut für Organische Chemie , Universität Würzburg , Am Hubland , 97074 Würzburg , Germany . Email: seibel@ 123456chemie.uni-wuerzburg
                [b ] Institut für Physikalische und Theoretische Chemie , Universität Würzburg , Emil-Fischer Strasse 42 , 97074 Würzburg , Germany
                [c ] Abteilung für Funktionswerkstoffe der Medizin und der Zahnheilkunde , Universitätsklinikum Würzburg , Pleicherwall 2 , D-97070 Würzburg , Germany
                [d ] Rudolf-Virchow-Zentrum für Experimentelle Biomedizin , Universität Würzburg , Josef-Schneider Str. 2, Haus D15 , 97080 Würzburg , Germany
                Author information
                http://orcid.org/0000-0002-4597-6360
                http://orcid.org/0000-0001-7057-5369
                http://orcid.org/0000-0002-8036-4853
                Article
                Publisher ID: c8sc01244j
                DOI: 10.1039/c8sc01244j
                PMC ID: 6009436
                PubMed ID: 30009003
                SO-VID: 2141344e-c9ed-4a9a-8941-c9a87cb521df
                Copyright © This journal is © The Royal Society of Chemistry 2018
                License:

                This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)

                History
                Date received : 16 March 2018
                Date accepted : 18 May 2018
                Categories
                Subject: Chemistry

                Notes

                †Electronic supplementary information (ESI) available. See DOI: 10.1039/c8sc01244j


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