Development and Application of a Solution-Phase Automated Synthesizer, 'ChemKonzert'

Machida, Kazuhiro; Hirose, Yoichiro; Fuse, Shinichiro; Sugawara, Tohru; Takahashi, Takashi

doi:10.1248/cpb.58.87

Cited by 38 publications

(25 citation statements)

References 13 publications

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“…The automation of synthetic procedures improves both the reproducibility and the reliability of the syntheses because automated synthesizers minimize the variability of the experimental manipulations 26. We carried out the synthesis of 10 including the key step, Ti III ‐catalyzed radical cyclization by using our originally developed automated synthesizer, ChemKonzert26c (for details of the automated synthesis of 10 , see the Supporting Information). This automation is noteworthy because the obtained compound 10 is useful for the synthesis of numerous bioactive natural products.…”

Section: Resultsmentioning

confidence: 99%

Asymmetric Total Synthesis of ent‐Pyripyropene A

Fuse

Ikebe

Oosumi

et al. 2015

Chemistry A European J

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An asymmetric total synthesis of ent-pyripyropene A was achieved by a convergent synthetic route. We used our originally developed Ti(III) -catalyzed radical cyclization to construct an AB-ring portion that consisted of a trans-decalin skeleton with five contiguous stereogenic centers. The coupling between the AB-ring and the DE-ring portions, and a subsequent C-ring cyclization, led to the total synthesis of ent-pyripyropene A. An evaluation of the insecticidal activity of ent-pyripyropene A against two aphid species revealed that ent-pyripyropene A was 35-175 times less active than naturally occurring pyripyropene A. This result indicated that the biological target of pyripyropene A recognizes the absolute configuration of pyripyropene A.

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Section: Resultsmentioning

confidence: 99%

Asymmetric Total Synthesis of ent‐Pyripyropene A

Fuse

Ikebe

Oosumi

et al. 2015

Chemistry A European J

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“…509,510 Discussed below is the development of “the first fully automated solid-phase oligosaccharide synthesizer” by Seeberger et al, initially in its experimental form, 456 that in 2014 was marketed as Glyconeer 2.1. Also discussed are other automation efforts, primarily by Takahashi, 511,512 Pohl, 513 Demchenko and Stine, 514 and Nokami and co-workers 515 that have been also emerging during about the same time-period.…”

Section: Automated Synthesis Of Oligosaccharidesmentioning

confidence: 99%

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

et al. 2018

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Advances in carbohydrate chemistry have certainly made common oligosaccharides much more accessible. However, many current methods still rely heavily upon specialized knowledge of carbohydrate chemistry. The application of automated technologies to chemical and life science applications such as genomics and proteomics represents a vibrant field. These automated technologies also present opportunities for their application to organic synthesis, including that of the synthesis of oligosaccharides. However, application of automated methods to the synthesis of carbohydrates is an underdeveloped area as compared to other classes of biomolecules. The overarching goal of this review article is to present the advances that have been made at the interface of carbohydrate chemistry and automated technology.

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“…Thus, digitisation has led to an explosion in cooperativity driven by common standards and protocols, which means that tasks centrally managed can be distributed over many sites, yet this approach has yet to impact the field of chemistry 4 , 5 . However, the automation of chemical reactions has been an expanding field in the last decade, including flow chemistry, peptide and nucleic acid synthesis 6 . These robotic systems are specialised and expensive ($50–500K) so the adoption of such automation in chemistry has been limited.…”

Section: Introductionmentioning

confidence: 99%

Networking chemical robots for reaction multitasking

et al. 2018

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The development of the internet of things has led to an explosion in the number of networked devices capable of control and computing. However, whilst common place in remote sensing, these approaches have not impacted chemistry due to difficulty in developing systems flexible enough for experimental data collection. Herein we present a simple and affordable (<$500) chemistry capable robot built with a standard set of hardware and software protocols that can be networked to coordinate many chemical experiments in real time. We demonstrate how multiple processes can be done with two internet-connected robots collaboratively, exploring a set of azo-coupling reactions in a fraction of time needed for a single robot, as well as encoding and decoding information into a network of oscillating reactions. The system can also be used to assess the reproducibility of chemical reactions and discover new reaction outcomes using game playing to explore a chemical space.

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Development and Application of a Solution-Phase Automated Synthesizer, 'ChemKonzert'

Cited by 38 publications

References 13 publications

Asymmetric Total Synthesis of ent‐Pyripyropene A

Asymmetric Total Synthesis of ent‐Pyripyropene A

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

Networking chemical robots for reaction multitasking

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