scholarly journals Antibody-catalyzed formation of a 14-membered ring lactone

2002 ◽  
Vol 80 (12) ◽  
pp. 1643-1645 ◽  
Author(s):  
Michael D Pungente ◽  
Larry Weiler ◽  
Hermann J Ziltener
Keyword(s):  
Monoclonal Antibody ◽  
Transition State ◽  
Active Site ◽  
Large Scale ◽  
Competitive Inhibition ◽  
Membered Ring ◽  
Catalytic Antibodies ◽  
Transition State Analogue ◽  
Catalytic Experiment ◽  
Ether Extraction

Monoclonal antibody (MAb) F123, raised against a macrocyclic phosphonate transition-state analogue, catalyzed an intramolecular transesterification of the corresponding hydroxy ester to give a 14-membered ring lactone. The MAb reaction displayed enzyme-like Michaelis–Menten kinetics with a Km of 255 µM and a kcat of 0.01 min–1 based on p-nitrophenol release and calculated on an active-site basis. Substrate specificity and competitive inhibition by a transition state analogue (Ki = 3 µM) demonstrated that the catalytic activity was associated with binding in the antibody-combining site. The lactone product was isolated from a large-scale catalytic experiment through ether extraction and identified by gas chromatography – mass spectroscopy.Key words: macrocyclization, lactones, catalytic antibodies.

Article

1998 ◽  
Vol 76 (3) ◽  
pp. 313-318
Author(s):  
Vito Ferro ◽  
Larry Weiler ◽  
Stephen G Withers ◽  
Herman Ziltener
Keyword(s):  
Transition State ◽  
Enzyme Inhibition ◽  
Catalytic Antibodies ◽  
Transition State Analogue ◽  
Amide Hydrolysis ◽  
Transition State Analogue Inhibitors

The synthesis of N-glycosyl phosphonamidates has been accomplished via the coupling of peracetylated glycosylamines with an appropriate phosphonochloridate in the presence of pyridine. The resulting glycosyl phosphonamidate esters are dealkylated with bromotrimethylsilane and then deacetylated to give the target compounds, which are potential transition-state analogue inhibitors of glycopeptidases and may prove useful as haptens for generating catalytic antibodies with glycopeptidase activity.Key words: enzyme inhibition, PNGase, phosphonamidate, amide hydrolysis.

scholarly journals A Trojan horse transition state analogue generated by MgF3- formation in an enzyme active site

2006 ◽  
Vol 103 (40) ◽  
pp. 14732-14737 ◽  
Author(s):  
N. J. Baxter ◽  
L. F. Olguin ◽  
M. Golicnik ◽  
G. Feng ◽  
A. M. Hounslow ◽  
...  
Keyword(s):  
Transition State ◽  
Active Site ◽  
Trojan Horse ◽  
Enzyme Active Site ◽  
Transition State Analogue

Comparison of Experimental and Theoretical Structures of a Transition State Analogue Used for the Induction of Anti-Cocaine Catalytic Antibodies

1997 ◽  
Vol 101 (45) ◽  
pp. 8526-8529 ◽  
Author(s):  
Edward C. Sherer ◽  
Ginger Yang ◽  
Gordon M. Turner ◽  
George C. Shields ◽  
Donald W. Landry
Keyword(s):  
Transition State ◽  
Catalytic Antibodies ◽  
Transition State Analogue

MgF3−and α-Galactose 1-Phosphate in the Active Site of β-Phosphoglucomutase Form a Transition State Analogue of Phosphoryl Transfer

2009 ◽  
Vol 131 (45) ◽  
pp. 16334-16335 ◽  
Author(s):  
Nicola J. Baxter ◽  
Andrea M. Hounslow ◽  
Matthew W. Bowler ◽  
Nicholas H. Williams ◽  
G. Michael Blackburn ◽  
...  
Keyword(s):  
Transition State ◽  
Active Site ◽  
Phosphoryl Transfer ◽  
Transition State Analogue
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