Regioselective benzoylation of unprotected β-glycopyranosides with benzoyl cyanide and an amine catalyst – application to saponin synthesis

2021 ◽  
Author(s):  
Tianlu Li ◽  
Tong Li ◽  
Yajing Sun ◽  
Yue Yang ◽  
Panpan Lv ◽  
...  
Keyword(s):  
Chemical Synthesis ◽  
Benzoyl Cyanide ◽  
Amine Catalysts

Regioselective protection of trans-trans triol and tetrol moieties in carbohydrates was achieved with BzCN as the benzoylating agent and amine catalysts. The protocols are useful for the chemical synthesis of oligosaccharides and saponins.

Catalytic Regioselective Benzoylation of 1,2-trans-Diols in Carbohydrates with Benzoyl Cyanide: The Axial Oxy Group Effect and the Action of Achiral and Chiral Amine Catalysts

ACS Catalysis ◽  
2020 ◽  
Vol 10 (19) ◽  
pp. 11406-11416 ◽  
Author(s):  
Tianlu Li ◽  
Tong Li ◽  
Michael Linseis ◽  
Fengshan Wang ◽  
Rainer F. Winter ◽  
...  
Keyword(s):  
Group Effect ◽  
Chiral Amine ◽  
Benzoyl Cyanide ◽  
Amine Catalysts

Chemical synthesis of proteinoids: Part 1

1964 ◽  
Author(s):  
Sidney W. Fox ◽  
Kaoru Harada ◽  
Gottfried Krampitz ◽  
Tadao Hayakawa ◽  
Charles Ray Windsor
Keyword(s):  
Chemical Synthesis

Chemical Synthesis of Peptides

2012 ◽  
Vol 2 (2) ◽  
pp. 147-149
Author(s):  
Tanaji Dnyanadev Padalkar ◽  
Keyword(s):  
Chemical Synthesis

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

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.

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

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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