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Literature DB >> 17994738

Development and initial application of a hybridization-independent, DNA-encoded reaction discovery system compatible with organic solvents.

Mary M Rozenman¹, Matthew W Kanan, David R Liu.

Abstract

We have developed and applied an approach to reaction discovery that takes advantage of DNA encoding, DNA-programmed assembly of substrate pairs, in vitro selection, and PCR amplification, yet does not require reaction conditions that support DNA hybridization. This system allows the simultaneous evaluation of >200 potential bond-forming combinations of substrates in a single experiment and can be applied in a range of solvent and temperature conditions. In an initial application, we applied this system to explore Au(III)-mediated chemistry and uncovered a simple, mild method for the selective Markovnikov-type hydroarylation of vinyl arenes and trisubstituted olefins with indoles.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 17994738 PMCID： PMC2538361 DOI： 10.1021/ja074155j

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

26 in total

Review 1. In vitro selection of functional nucleic acids.

Authors: D S Wilson; J W Szostak
Journal: Annu Rev Biochem Date: 1999 Impact factor: 23.643

2. Gold-catalyzed intramolecular reaction of indoles with alkynes: facile formation of eight-membered rings and an unexpected allenylation.

Authors: Catalina Ferrer; Antonio M Echavarren
Journal: Angew Chem Int Ed Engl Date: 2006-02-06 Impact factor: 15.336

3. Efficient metal-catalyzed hydroarylation of styrenes.

Authors: Magnus Rueping; Boris J Nachtsheim; Thomas Scheidt
Journal: Org Lett Date: 2006-08-17 Impact factor: 6.005

Review 4. Relativistic effects in homogeneous gold catalysis.

Authors: David J Gorin; F Dean Toste
Journal: Nature Date: 2007-03-22 Impact factor: 49.962

5. Brønsted acid catalyzed addition of phenols, carboxylic acids, and tosylamides to simple olefins.

Authors: Zigang Li; Junliang Zhang; Chad Brouwer; Cai-Guang Yang; Nicholas W Reich; Chuan He
Journal: Org Lett Date: 2006-09-14 Impact factor: 6.005

6. A convenient FeCl3-catalyzed hydroarylation of styrenes.

Authors: Jette Kischel; Irina Jovel; Kristin Mertins; Alexander Zapf; Matthias Beller
Journal: Org Lett Date: 2006-01-05 Impact factor: 6.005

7. Highly efficient addition of activated methylene compounds to alkenes catalyzed by gold and silver.

Authors: Xiaoquan Yao; Chao-Jun Li
Journal: J Am Chem Soc Date: 2004-06-09 Impact factor: 15.419

8. Enantioselective Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes.

Authors: David A Evans; Keith R Fandrick; Hyun-Ji Song; Karl A Scheidt; Risheng Xu
Journal: J Am Chem Soc Date: 2007-07-21 Impact factor: 15.419

9. Gold(I)-catalyzed intramolecular enantioselective hydroarylation of allenes with indoles.

Authors: Cong Liu; Ross A Widenhoefer
Journal: Org Lett Date: 2007-04-12 Impact factor: 6.005

10. Platinum-catalyzed intramolecular alkylation of indoles with unactivated olefins.

Authors: Cong Liu; Xiaoqing Han; Xiang Wang; Ross A Widenhoefer
Journal: J Am Chem Soc Date: 2004-03-31 Impact factor: 15.419

20 in total

1. Synthesis and Preliminary Biological Study of Bisindolylmethanes Accessed by an Acid-Catalyzed Hydroarylation of Vinylindoles.

Authors: Tejas P Pathak; Jaroslaw G Osiak; Rachel M Vaden; Bryan E Welm; Matthew S Sigman
Journal: Tetrahedron Date: 2012-07-01 Impact factor: 2.457

Review 2. The structural stability and catalytic activity of DNA and RNA oligonucleotides in the presence of organic solvents.

Authors: Shu-Ichi Nakano; Naoki Sugimoto
Journal: Biophys Rev Date: 2016-01-11

Development and initial application of a hybridization-independent, DNA-encoded reaction discovery system compatible with organic solvents.

Review 1. In vitro selection of functional nucleic acids.

2. Gold-catalyzed intramolecular reaction of indoles with alkynes: facile formation of eight-membered rings and an unexpected allenylation.

3. Efficient metal-catalyzed hydroarylation of styrenes.

Review 4. Relativistic effects in homogeneous gold catalysis.

5. Brønsted acid catalyzed addition of phenols, carboxylic acids, and tosylamides to simple olefins.

6. A convenient FeCl3-catalyzed hydroarylation of styrenes.

7. Highly efficient addition of activated methylene compounds to alkenes catalyzed by gold and silver.

8. Enantioselective Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes.

9. Gold(I)-catalyzed intramolecular enantioselective hydroarylation of allenes with indoles.

10. Platinum-catalyzed intramolecular alkylation of indoles with unactivated olefins.

1. Synthesis and Preliminary Biological Study of Bisindolylmethanes Accessed by an Acid-Catalyzed Hydroarylation of Vinylindoles.

Review 2. The structural stability and catalytic activity of DNA and RNA oligonucleotides in the presence of organic solvents.

3. Thermal Stability of RNA Structures with Bulky Cations in Mixed Aqueous Solutions.

Review 4. Small-molecule discovery from DNA-encoded chemical libraries.

Review 5. Contemporary screening approaches to reaction discovery and development.

6. Discovery of an α-amino C-H arylation reaction using the strategy of accelerated serendipity.

7. A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

8. A simple, multidimensional approach to high-throughput discovery of catalytic reactions.

9. Reaction discovery employing macrocycles: transannular cyclizations of macrocyclic bis-lactams.

10. Reactivity-dependent PCR: direct, solution-phase in vitro selection for bond formation.