Aspidosperma Terpenoid Alkaloids — Biosynthetic Origin, Chemical Synthesis and Importance

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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Controlling Gas Selectivity in Molecular Porous Liquids by Tuning the Cage Window Size

10.26434/chemrxiv.10247528.v1 ◽

2019 ◽

Author(s):

Benjamin Egleston ◽

Konstantin V. Luzyanin ◽

Michael C. Brand ◽

Rob Clowes ◽

Michael E. Briggs ◽

...

Keyword(s):

Nmr Spectroscopy ◽

Chemical Synthesis ◽

Field Gradient ◽

Window Size ◽

Standard Approach ◽

Porous Solids ◽

Pulsed Field Gradient Nmr ◽

Pulsed Field ◽

Cage Molecules ◽

Gas Selectivity

Control of pore window size is the standard approach for tuning gas selectivity in porous solids. Here, we present the first example where this is translated into a molecular porous liquid formed from organic cage molecules. Reduction of the cage window size by chemical synthesis switches the selectivity from Xe-selective to CH4-selective, which is understood using 129Xe, 1H, and pulsed-field gradient NMR spectroscopy.

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