Enzymatic resolution of γ-carboxy-DL-glutamic acid

1984 ◽  
Vol 49 (11) ◽  
pp. 2562-2565 ◽  
Author(s):  
Václav Čeřovský ◽  
Karel Jošt
Keyword(s):  
Glutamic Acid ◽  
Optically Active ◽  
Protecting Groups ◽  
Subsequent Removal ◽  
Enzymatic Resolution ◽  
Enantioselective Reaction

Optically active γ-carboxy-L-glutamic acid was prepared by enantioselective reaction of benzyloxycarbonyl-γ-carboxy-DL-glutamic acid with phenylhydrazine, catalyzed by papain (E.C.3.4.22.2), and subsequent removal of the protecting groups from the obtained benzyloxycarbonyl-γ-carboxy-L-glutamic acid α-phenylhydrazide.

Enzymatically catalyzed synthesis of dipeptides of γ-carboxy-L-glutamic acid from benzyloxycarbonyl-γ-carboxy-DL-glutamic acid

1985 ◽  
Vol 50 (4) ◽  
pp. 878-884 ◽  
Author(s):  
Václav Čeřovský ◽  
Karel Jošt
Keyword(s):  
Amino Acids ◽  
Glutamic Acid ◽  
Protecting Groups ◽  
Enantioselective Reaction

Enantioselective reaction of benzyloxycarbonyl-γ-carboxy-DL-glutamic acid with phenylhydrazides of various amino acids and with leucine, protected with various carboxy-protecting groups, has been studied.

scholarly journals PREPARATION OF d(-)-GLUTAMIC ACID FROM dl-GLUTAMIC ACID BY ENZYMATIC RESOLUTION

1940 ◽  
Vol 133 (3) ◽  
pp. 703-705
Author(s):  
Joseph S. Fruton ◽  
George W. Irving ◽  
Max Bergmann
Keyword(s):  
Glutamic Acid ◽  
Enzymatic Resolution

On the Chemistry of Ingenol, III [1] Synthesis of 3-Deoxy-3-oxoingenol, Some 5-Esters and of Ethers and Acetals of Ingenol

1982 ◽  
Vol 37 (12) ◽  
pp. 1640-1647 ◽  
Author(s):  
Bernd Sorg ◽  
Erich Hecker
Keyword(s):  
Good Yield ◽  
Protecting Groups ◽  
Silyl Ether ◽  
Subsequent Removal ◽  
Mouse Ear

3-Deoxy-3-oxoingenol (3) was prepared from ingenol-5,20-acetonide (25) by oxidation and subsequent removal of the acetonide. 3 was acylated to give homologous 5,20-diacylates 5-9. From these the 5-monoacylates 14, 15 and 17 were obtained in only moderate yields. Therefore the 20-silyl ether 10 (prepared from 3) was acylated. After smooth removal of the silyl ether the homologous 5-acylates 16. 18 and 19 resulted in good yield. The 5,20-dibutyrate 6 and all 5-acylates prepared (14-19) showed no irritant activity on the mouse ear. The 3-oxo-5-acylates 14-19 could not be reduced to give ingenol-5-acylates (24). Therefore various ingenol derivatives, 29-32, with suitable protected hydroxyl functions as well as the corresponding 5-clecanoates 35-38 were synthesized. The protecting groups of the derivatives 35-38 could however not be cleaved off to yield ingenol-5- decanoate (24)

Synthesis of optically active arylene bis-alanine derivatives carrying orthogonal protecting groups

1998 ◽  
Vol 9 (3) ◽  
pp. 503-512 ◽  
Author(s):  
Andreas Ritzén ◽  
Basudeb Basu ◽  
Shital K. Chattopadhyay ◽  
Fahreen Dossa ◽  
Torbjörn Frejd
Keyword(s):  
Optically Active ◽  
Protecting Groups

Scale-up of the enantioselective reaction for the enzymatic resolution of (R,S)-ibuprofen

1995 ◽  
Vol 17 (10) ◽  
pp. 1095-1098 ◽  
Author(s):  
M. Trani ◽  
A. Ducret ◽  
P. Pepin ◽  
R. Lortie
Keyword(s):  
Scale Up ◽  
Enzymatic Resolution ◽  
Enantioselective Reaction
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