Analysis of the Enol Ether Transfer Catalyzed by UDP-GlcNAc Enolpyruvyl Transferase Using (E)- and (Z)-Isomers of Phosphoenolbutyrate: Stereochemical, Partitioning, and Isotope Effect Studies

1995 ◽  
Vol 117 (28) ◽  
pp. 7329-7337 ◽  
Author(s):  
Watson J. Lees ◽  
Christopher T. Walsh
2016 ◽  
Vol 14 (26) ◽  
pp. 6289-6296 ◽  
Author(s):  
Pranab K. Bhadra ◽  
Abdolreza Hassanzadeh ◽  
Biljana Arsic ◽  
David G. Allison ◽  
Gareth A. Morris ◽  
...  

An efficient synthesis of 8-d-erythromycin B was achieved. A deuterium isotope effect suppresses formation of the corresponding enol ether, which may result in reduced gut-motilide effects.


1998 ◽  
Vol 93 (5) ◽  
pp. 801-807
Author(s):  
JOACHIM SCHULTE ◽  
MICHAEL BOHM ◽  
RAFAEL RAMIREZ

1993 ◽  
Vol 3 (3) ◽  
pp. 871-885 ◽  
Author(s):  
P. Auban-Senzier ◽  
C. Bourbonnais ◽  
D. Jérome ◽  
C. Lenoir ◽  
P. Batail ◽  
...  

2020 ◽  
Author(s):  
Rui Guo ◽  
Xiaotian Qi ◽  
Hengye Xiang ◽  
Paul Geaneoates ◽  
Ruihan Wang ◽  
...  

Vinyl fluorides play an important role in drug development as they serve as bioisosteres for peptide bonds and are found in a range of biologically active molecules. The discovery of safe, general and practical procedures to prepare vinyl fluorides remains an important goal and challenge for synthetic chemistry. Here we introduce an inexpensive and easily-handled reagent and report simple, scalable, and metal-free protocols for the regioselective and stereodivergent hydrofluorination of alkynes to access both the E and Z isomers of vinyl fluorides. These conditions were suitable for a diverse collection of alkynes, including several highly-functionalized pharmaceutical derivatives. Mechanistic and DFT studies support C–F bond formation through a vinyl cation intermediate, with the (E)- and (Z)-hydrofluorination products forming under kinetic and thermodynamic control, respectively.<br>


2021 ◽  
Vol 125 (9) ◽  
pp. 1910-1918
Author(s):  
Chih-Kai Lin ◽  
Qian-Rui Huang ◽  
Ying-Cheng Li ◽  
Ha-Quyen Nguyen ◽  
Jer-Lai Kuo ◽  
...  

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