N → O acyl-transfer reaction catalyzed by antibodies

Journal of the American Chemical Society

Volumn 118, Issue 51, 1996, Pages 13077-13078

  Ersoy, Oguz ^a,b   Fleck, Roman ^a   Sinskey, Anthony ^a   Masamune, Satoru ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b KAROLINSKA INSTITUTE   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODY;

ARTICLE; CATALYSIS; HYDROLYSIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030473366     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963026s     Document Type: Article

References (31)

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2. For recent reviews on Catalytic Antibodies see (a) Lerner, R. A.; Benkovic, S. J.; Schultz, P. G. Science 1991, 252, 659. (b) Schultz, P. G.; Lerner, R. A. Acc. Chem Res. 1993, 26, 391. (c) Schultz, P. G.; Lemer, R. A. Science 1995, 269, 1835. (d) MacBeath, G.; Hilvert, D. Chem. Biol. 1996, 3(6), 433.
3. For recent reviews on Catalytic Antibodies see (a) Lerner, R. A.; Benkovic, S. J.; Schultz, P. G. Science 1991, 252, 659. (b) Schultz, P. G.; Lerner, R. A. Acc. Chem Res. 1993, 26, 391. (c) Schultz, P. G.; Lemer, R. A. Science 1995, 269, 1835. (d) MacBeath, G.; Hilvert, D. Chem. Biol. 1996, 3(6), 433.
4. For recent reviews on Catalytic Antibodies see (a) Lerner, R. A.; Benkovic, S. J.; Schultz, P. G. Science 1991, 252, 659. (b) Schultz, P. G.; Lerner, R. A. Acc. Chem Res. 1993, 26, 391. (c) Schultz, P. G.; Lemer, R. A. Science 1995, 269, 1835. (d) MacBeath, G.; Hilvert, D. Chem. Biol. 1996, 3(6), 433.
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14. Aspartic proteases are supposed to use an external water molecule for the initial nucleophilic attack.
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26. This background rate is in accordance with a previously determined background rate for a similar p-nitroanilide substrate, see ref 2.
27. 10 mM is the solubility limit of the haptens in water.
28. i at pH 8.0 and higher could not be determined due to the instability of hapten O1 at this pH.
29. We have observed a similar phenomenon in our previous studies, see ref 5b.
30. Preliminary results showed that antibody 14-10 displays a bell shaped pH-rate profile suggesting two ionizable binding site residues that participate in catalysis. However, further investigations will be carried out to support this hypothesis and will be the subject of a full account of our work.
31. There is a remote possibility that the hydroxyl group is only needed for binding, and that catalysis occurs by some other mechanism.