Templated chemistry for bioorganic synthesis and chemical biology

Seitz, Oliver

doi:10.1002/psc.3198

Cited by 17 publications

(13 citation statements)

References 152 publications

(282 reference statements)

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“…T emplated chemistry is a hallmark of biological processes, bringing reactants into close proximity with one another, thus greatly increasing effective molarity and dramatically raising the rate of reaction [1][2][3] . Many reactions that would otherwise not occur in practical time periods are facilitated by templating.…”

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confidence: 99%

Traceless native chemical ligation of lipid-modified peptide surfactants by mixed micelle formation

et al. 2020

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Biology utilizes multiple strategies, including sequestration in lipid vesicles, to raise the rate and specificity of chemical reactions through increases in effective molarity of reactants. We show that micelle-assisted reaction can facilitate native chemical ligations (NCLs) between a peptide-thioesterin which the thioester leaving group contains a lipid-like alkyl chainand a Cys-peptide modified by a lipid-like moiety. Hydrophobic lipid modification of each peptide segment promotes the formation of mixed micelles, bringing the reacting peptides into close proximity and increasing the reaction rate. The approach enables the rapid synthesis of polypeptides using low concentrations of reactants without the need for thiol catalysts. After NCL, the lipid moiety is removed to yield an unmodified ligation product. This micelle-based methodology facilitates the generation of natural peptides, like Magainin 2, and the derivatization of the protein Ubiquitin. Formation of mixed micelles from lipid-modified reactants shows promise for accelerating chemical reactions in a traceless manner.

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confidence: 99%

Traceless native chemical ligation of lipid-modified peptide surfactants by mixed micelle formation

et al. 2020

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“…From adhesive properties of gecko feet to the dazzling colors exhibited by Morpho butterfly wings, nature’s creatures display extraordinary physical and chemical properties that can arise from materials in hierarchical form. − Yet translating the hierarchical motifs present in nature’s materials to engineered nanostructured materials is difficult to achieve by traditional material-processing techniques. ,− Engineered nanomaterials with hierarchical features are commonly prepared through top-down approaches ( e.g. , lithography); however, these strategies suffer from (i) complex environments and instrumentation, (ii) difficulties in scalability, and (iii) high production costs. − In contrast, hierarchical structures produced by biological systems typically arise through bottom-up synthetic processes in which the size, shape, functionality, and crystal structure of the materials are well-defined throughout material formation. − ,, Mimicking the templating observed in some biological sysems, hierarchically porous inorganic materials have been synthesized; however, these synthetic inorganic systems often lack fine structural control. − …”

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confidence: 99%

Kinetically Controlled Sequential Seeded Growth: A General Route to Crystals with Different Hierarchies

et al. 2020

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The organization of natural materials into hierarchical structures accounts for the amazing properties of many biological systems; however, translating the structural motifs present in such natural materials to synthetic systems remains difficult. Inspired by how nature creates materials, this work demonstrates that kinetically controlled sequential seeded growth is a general bottom-up strategy to prepare hierarchical inorganic crystals with distinct compositions and nanostructured forms. Specifically, 85 distinct hierarchical crystals with different shape-controlled features, compositions, and overall symmetries were readily achieved by altering the kinetics of metal deposition in sequential rounds of seeded growth. These modifications in the deposition kinetics were achieved through simple changes to the reaction conditions (e.g., pH or halide concentration) and dictate whether concave or convex features are produced at specific seed locations, much in the manner that the changing atmospheric conditions account for the hierarchical and symmetrical structures of snow crystals. As such, this work provides a general paradigm for the bottom-up synthesis of hierarchical crystals regardless of inorganic material class.

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“…The metaarrangement allowed cleft formation and complementary DNA formation. Overall, TAPbased meta-arrangement with 1,8-naphthalimide-functionalized ruthenium complexes (8,9) showed enhanced DNA-photocleavage properties compared with Ru(bpy)-based 1,8-naphthalimide-functionalized complexes (10,11). In particular, compound 8 showed full conversion to the open form of the plasmid (1 mg/mL) within 30 min of irradiation.…”

Section: Ru Complex-based Methodsmentioning

confidence: 94%

“…To develop these technologies, chemical reactions, such as chemical bond formation or cleavage of the (1) nucleic acid or (2) external molecules bound to nucleic acids have been studied [ 9 ]. These reactions have brought new concepts of molecular performance, which were not observed in canonical unmodified nucleic acid strands, and have resulted in remarkable improvements in nucleic acid-sensing, drug synthesis and release, nucleic acid nanotechnology, and molecular therapy [ 9 , 10 , 11 , 12 , 13 , 14 , 15 ]. In this context, the development of new bioorthogonal reactions for nucleic acids has a potential to accelerate the expansion of the scope of nucleic acid-based technologies.…”

Section: Introductionmentioning

confidence: 99%

Visible Light Photochemical Reactions for Nucleic Acid-Based Technologies

et al. 2021

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The expanding scope of chemical reactions applied to nucleic acids has diversified the design of nucleic acid-based technologies that are essential to medicinal chemistry and chemical biology. Among chemical reactions, visible light photochemical reaction is considered a promising tool that can be used for the manipulations of nucleic acids owing to its advantages, such as mild reaction conditions and ease of the reaction process. Of late, inspired by the development of visible light-absorbing molecules and photocatalysts, visible light-driven photochemical reactions have been used to conduct various molecular manipulations, such as the cleavage or ligation of nucleic acids and other molecules as well as the synthesis of functional molecules. In this review, we describe the recent developments (from 2010) in visible light photochemical reactions involving nucleic acids and their applications in the design of nucleic acid-based technologies including DNA photocleaving, DNA photoligation, nucleic acid sensors, the release of functional molecules, and DNA-encoded libraries.

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Templated chemistry for bioorganic synthesis and chemical biology

Cited by 17 publications

References 152 publications

Traceless native chemical ligation of lipid-modified peptide surfactants by mixed micelle formation

Traceless native chemical ligation of lipid-modified peptide surfactants by mixed micelle formation

Kinetically Controlled Sequential Seeded Growth: A General Route to Crystals with Different Hierarchies

Visible Light Photochemical Reactions for Nucleic Acid-Based Technologies

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