Synthesis of the Isocyanide Building Block Asmic, anisylsulfanylmethylisocyanide

Herein, we report the semisynthetic production of the potent transient receptor potential canonical (TRPC) channel agonist (−)-englerin A (EA), using guaia-6,10(14)-diene as the starting material. Guaia-6,10(14)-diene was systematically engineered in Escherichia coli and Saccharomyces cerevisiae using the CRISPR/Cas9 system and produced with high titers. This provided us the opportunity to execute a concise chemical synthesis of EA and the two related guaianes (−)-oxyphyllol and (+)-orientalol E. The potentially scalable approach combines the advantages of synthetic biology and chemical synthesis and provides an efficient and economical method for producing EA as well as its analogs.

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Microbe Engineering of Guaia-6,10(14)-diene as a Building Block for the Semisynthetic Production of Plant-Derived (−)-Englerin A

10.26434/chemrxiv.10333625 ◽

2019 ◽

Author(s):

Thomas Siemon ◽

Zhangqian Wang ◽

Guangkai Bian ◽

Tobias Seitz ◽

Ziling Ye ◽

...

Keyword(s):

Escherichia Coli ◽

Saccharomyces Cerevisiae ◽

Synthetic Biology ◽

Chemical Synthesis ◽

Building Block ◽

Transient Receptor Potential ◽

Receptor Potential ◽

Economical Method ◽

Englerin A ◽

Transient Receptor

Herein, we report the semisynthetic production of the potent transient receptor potential canonical (TRPC) channel agonist (−)-englerin A (EA), using guaia-6,10(14)-diene as the starting material. Guaia-6,10(14)-diene was systematically engineered in Escherichia coli and Saccharomyces cerevisiae using the CRISPR/Cas9 system and produced with high titers. This provided us the opportunity to execute a concise chemical synthesis of EA and the two related guaianes (−)-oxyphyllol and (+)-orientalol E. The potentially scalable approach combines the advantages of synthetic biology and chemical synthesis and provides an efficient and economical method for producing EA as well as its analogs.

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Ultrastrong, Free-Standing and Large Nanofilms of Pyrenearamid

10.26434/chemrxiv.8182088 ◽

2019 ◽

Author(s):

Amalia Rapakousiou ◽

Alejandro López-moreno ◽

Belén Nieto-Ortega ◽

M. Mar Bernal ◽

Miguel A. Monclús ◽

...

Keyword(s):

Mechanical Properties ◽

Building Block ◽

Aromatic Polyamide ◽

Free Standing ◽

Spatial Confinement ◽

Polymeric Structure ◽

Reduced Modulus ◽

Organizational Arrangement ◽

Polycyclic Aromatic ◽

Nanoscale Building Block

We introduce poly(1,6-pyrene terephthalamide) polymer (PPyrTA) as an aromatic polyamide analogue of poly(p-phenylene terephthalamide) (PPTA), also known as Kevlar®. This work shows that the incorporation of polycyclic aromatic pyrene moieties improves drastically the mechanical properties of the polymeric structure, increasing elastic nanoindentation-determined modulus and hardness by factors of 1.9 and 4.3, respectively. Liquid deprotonated dispersions of PPyrTA nanofibers were used as nanoscale building block for producing large-surface, free-standing polymer macroscopic nanofilms. This 2D assembly leads to further significant improvements in reduced modulus and hardness (more than twice) compared to the starting polymer macroscale fibres, due to a better re-organizational arrangement of the PPyrTA nanofibers in the nanofilms, formed under 2D spatial confinement.

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Thienopyrrolocarbazoles: New Building Blocks for Functional Organic Materials

10.26434/chemrxiv.7777343.v1 ◽

2019 ◽

Cited By ~ 1

Author(s):

Dorian Bader ◽

Johannes Fröhlich ◽

Paul Kautny

Keyword(s):

Building Block ◽

Organic Materials ◽

Building Blocks ◽

Molecular Properties ◽

The Family ◽

Facile Preparation

The facile preparation of three regioisomeric thienopyrrolocarbazoles applying a convenient C-H activation approach is presented. Derived from indolo[3,2,1-<i>jk</i>]carbazole, the incorporation of thiophene into the triarylamine framework significantly impacted the molecular properties of the parent scaffold. The developed thienopyrrolocarbazoles enrich the family of triarylamine donors and constitute a novel building block for functional organic materials.

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Thienopyrrolocarbazoles: New Building Blocks for Functional Organic Materials

10.26434/chemrxiv.7777343 ◽

2019 ◽

Author(s):

Dorian Bader ◽

Johannes Fröhlich ◽

Paul Kautny

Keyword(s):

Building Block ◽

Organic Materials ◽

Building Blocks ◽

Molecular Properties ◽

The Family ◽

Facile Preparation

The facile preparation of three regioisomeric thienopyrrolocarbazoles applying a convenient C-H activation approach is presented. Derived from indolo[3,2,1-<i>jk</i>]carbazole, the incorporation of thiophene into the triarylamine framework significantly impacted the molecular properties of the parent scaffold. The developed thienopyrrolocarbazoles enrich the family of triarylamine donors and constitute a novel building block for functional organic materials.

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