Antibody catalysis of cyclohexadienone rearrangments

Details Antibody catalysis of cyclohexadienone rearrangments Antibody catalysis of cyclohexadienone rearrangments

1994-08-18

1996-03-19

Patterson, Jr., Charles L.

Chemistry: molecular biology and microbiology

Micro-organism, tissue cell culture or enzyme using process...

Preparing oxygen-containing organic compound

4351885, 43524026, 43524027, C12P 722, C12N 900

Patent

active

055003583

ABSTRACT:
Catalytic antibodies are employed for catalyzing rearrangement reactions involving carbon-carbon bonds. The catalytic antibodies are generated using haptens that are transition state analogs of the such rearrangement reactions. More particularly, the haptens dispslay an electrostatic complementarity with the transition state. Since the formation of a transient positive charge in the migrating bond is a general feature of nucleophilic 1,2-shifts, it is disclosed that haptens for generating catalytic antibody directed to such reactions must incorporate such charge. Antibody catalysis of the dienone-phenol rearrangement is shown to catalyze both the hydronium ion promoted pathway and the spontaneous rearrangement pathway, indicating that the antibody stabilizes the localized positive charge of the transition state.

REFERENCES:
Hart, et al., "Synthesis of 6H-DiBenzo[b,d]Pyran-6-Ones Via Dienone Phenol Rearrangements of Spiro[2,5-Cyclohexadiene-1,1'(3+H)-Iso Benzofuran]-3'-Ones", Tetrahedron, 48: 8179-8188 (1992).
Miller, B., "Too Many Rearrangemetns of Cyclohexadienones", Accounts of Chemical Research, 8: 245-256 (1975).
Valderrama, et al., "Studies on Quinones. XV. A Convenient Entry Into the Tetrahydrophenanthrene-1,4-Quinone System Utilizing the Dienone-Phenol Rearrangement of Spiro [Cyclo Pentanenaphthalene]Triones", Tet. Lett., 26: 6281-6284 (1985).

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