Isocyanide‐Based Multicomponent Reactions: A Concise Approach to 2‐Amino‐3‐perfluoroalkylfurans Using Methyl Perfluoroalk‐2‐ynoates as Fluorinated Building Blocks

2019 ◽  
Vol 8 (5) ◽  
pp. 710-715 ◽  
Author(s):  
Yedong Wang ◽  
Lili Tao ◽  
Jie Chen ◽  
Weimin He ◽  
Hongmei Deng ◽  
...  
Keyword(s):  
Multicomponent Reactions ◽  
Building Blocks ◽  
Fluorinated Building Blocks

scholarly journals Droplet-Assisted Microfluidic Fabrication and Characterization of Multifunctional Polysaccharide Microgels Formed by Multicomponent Reactions

Polymers ◽  
2018 ◽  
Vol 10 (10) ◽  
pp. 1055 ◽  
Author(s):  
Nicolas Hauck ◽  
Nalin Seixas ◽  
Silvia Centeno ◽  
Raimund Schlüßler ◽  
Gheorghe Cojoc ◽  
...  
Keyword(s):  
Hyaluronic Acid ◽  
Multicomponent Reactions ◽  
Building Blocks ◽  
Correlation Spectroscopy ◽  
Droplet Microfluidics ◽  
Phase Imaging ◽  
Colloidal Probe ◽  
Young’S Moduli ◽  
Depth Analysis ◽  
The Impact

Polysaccharide-based microgels have broad applications in multi-parametric cell cultures, cell-free biotechnology, and drug delivery. Multicomponent reactions like the Passerini three-component and the Ugi four-component reaction are shown in here to be versatile platforms for fabricating these polysaccharide microgels by droplet microfluidics with a narrow size distribution. While conventional microgel formation requires pre-modification of hydrogel building blocks to introduce certain functionality, in multicomponent reactions one building block can be simply exchanged by another to introduce and extend functionality in a library-like fashion. Beyond synthesizing a range of polysaccharide-based microgels utilizing hyaluronic acid, alginate and chitosan, exemplary in-depth analysis of hyaluronic acid-based Ugi four-component gels is conducted by colloidal probe atomic force microscopy, confocal Brillouin microscopy, quantitative phase imaging, and fluorescence correlation spectroscopy to elucidate the capability of microfluidic multicomponent reactions for forming defined polysaccharide microgel networks. Particularly, the impact of crosslinker amount and length is studied. A higher network density leads to higher Young’s moduli accompanied by smaller pore sizes with lower diffusion coefficients of tracer molecules in the highly homogeneous network, and vice versa. Moreover, tailored building blocks allow for crosslinking the microgels and incorporating functional groups at the same time as demonstrated for biotin-functionalized, chitosan-based microgels formed by Ugi four-component reaction. To these microgels, streptavidin-labeled enzymes are easily conjugated as shown for horseradish peroxidase (HRP), which retains its activity inside the microgels.

scholarly journals Rapid approach to complex boronic acids

2019 ◽  
Vol 5 (7) ◽  
pp. eaaw4607 ◽  
Author(s):  
Constantinos G. Neochoritis ◽  
Shabnam Shaabani ◽  
Maryam Ahmadianmoghaddam ◽  
Tryfon Zarganes-Tzitzikas ◽  
Li Gao ◽  
...  
Keyword(s):  
Small Molecules ◽  
Boronic Acid ◽  
Multicomponent Reactions ◽  
Chemical Space ◽  
Building Blocks ◽  
Acid Synthesis ◽  
Success Rates ◽  
Boronic Acid Derivatives ◽  
Low Coverage ◽  
Target Synthesis

The compatibility of free boronic acid building blocks in multicomponent reactions to readily create large libraries of diverse and complex small molecules was investigated. Traditionally, boronic acid synthesis is sequential, synthetically demanding, and time-consuming, which leads to high target synthesis times and low coverage of the boronic acid chemical space. We have performed the synthesis of large libraries of boronic acid derivatives based on multiple chemistries and building blocks using acoustic dispensing technology. The synthesis was performed on a nanomole scale with high synthesis success rates. The discovery of a protease inhibitor underscores the usefulness of the approach. Our acoustic dispensing–enabled chemistry paves the way to highly accelerated synthesis and miniaturized reaction scouting, allowing access to unprecedented boronic acid libraries.

scholarly journals A fluoride-responsive genetic circuit enables in vivo biofluorination in engineered Pseudomonas putida

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Patricia Calero ◽  
Daniel C. Volke ◽  
Phillip T. Lowe ◽  
Charlotte H. Gotfredsen ◽  
David O’Hagan ◽  
...  
Keyword(s):  
Pseudomonas Putida ◽  
Building Blocks ◽  
T7 Rna Polymerase ◽  
Genetic Circuit ◽  
Gene Circuits ◽  
Fluorinated Building Blocks ◽  
Synthetic Gene Circuits ◽  
Cell Factories ◽  
Synthetic Circuit

Abstract Fluorine is a key element in the synthesis of molecules broadly used in medicine, agriculture and materials. Addition of fluorine to organic structures represents a unique strategy for tuning molecular properties, yet this atom is rarely found in Nature and approaches to integrate fluorometabolites into the biochemistry of living cells are scarce. In this work, synthetic gene circuits for organofluorine biosynthesis are implemented in the platform bacterium Pseudomonas putida. By harnessing fluoride-responsive riboswitches and the orthogonal T7 RNA polymerase, biochemical reactions needed for in vivo biofluorination are wired to the presence of fluoride (i.e. circumventing the need of feeding expensive additives). Biosynthesis of fluoronucleotides and fluorosugars in engineered P. putida is demonstrated with mineral fluoride both as only fluorine source (i.e. substrate of the pathway) and as inducer of the synthetic circuit. This approach expands the chemical landscape of cell factories by providing alternative biosynthetic strategies towards fluorinated building-blocks.

Selected Research Topics of the Dondoni Group over the Last Two Decades (2000–2020)

Synlett ◽  
2020 ◽  
Vol 31 (14) ◽  
pp. 1361-1371 ◽  
Author(s):  
Alessandro Dondoni
Keyword(s):  
Amino Acids ◽  
Bioorganic Chemistry ◽  
Multicomponent Reactions ◽  
Building Blocks ◽  
Synthetic Methods ◽  
Research Topics ◽  
Main Target ◽  
Sulfur Fluoride ◽  
Primary Rule ◽  
Selection Of

From a selection of research topics carried out in our laboratory during the last twenty years it becomes apparent that our main target was the discovery of new or improved synthetic methods together with new properties. Our efforts were made with the aim of being of some utility to other fields of research, with particular emphasis to glycobiology and heterocyle-based bioorganic chemistry. We performed new chemistry mainly in the field of carbohydrate manipulations taking as a primary rule the simplicity and efficiency manners. Toward this end, modern synthetic tools and approaches were employed such as heterocyle-based transformations, multicomponent reactions, organocatalysis, click azide–alkyne cycloadditions, reactions in ionic liquids, click photoinduced thiol-ene coupling, and click sulfur–fluoride exchange chemistry. With these potent methodologies in hand, the syntheses of carbohydrate containing amino acids up to proteins glycosylation were performed.1 Heterocyclic Glycoconjugates and Amino Acids2 Triazole-Linked Oligonucleotides: Application of Click CuAAC3 Non-Natural Glycosyl Amino Acids4 Non-Natural Oligosaccharides5 Calixarene-Based Glycoclusters6 Carbohydrate-Based Building Blocks7 Homoazasugars and Aza-C-disaccharides8 Synthesis of Glycodendrimers9 Peptide and Protein Glycoconjugates10 Conclusions

Toward the synthesis of novel fluorinated building blocks: 3,4-difluorothiophene-1,1-dioxide

1999 ◽  
Vol 93 (1) ◽  
pp. 27-31 ◽  
Author(s):  
Ireneusz Nowak ◽  
Lillian M. Rogers ◽  
Robin D. Rogers ◽  
Joseph S. Thrashe
Keyword(s):  
Building Blocks ◽  
Fluorinated Building Blocks
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