THE PHOTOLYTIC PRODUCTION OF LUMITETRACYCLINE FROM TETRACYCLINE AND THE PHOTOLYTIC INTERACTION OF TETRACYCLINE WITH CALF-THYMUS DNA
Abstract
A new photoproduct of tetracycline has been isolated (lumitetracycline, LTc) from the photolysis of Tc in a polar organic solvent (typically acetonitrile) using long wavelength ultraviolet light ($\lambda\ >$ 330 nm) and continuous argon degassing. By using uv absorbance, exact mass, and advance NMR techniques, the structure was determined to be a norbornyl derivative arising from the formation of a new bond between C(4) and C(11a) and the loss of dimethylamine. The product formation is quenched by oxygen but promoted by acetic acid and triethylamine. We have also demonstrated that photoproducts of Tc will bind to denatured calf-thymus DNA even in the dark. The level of binding ranges from 10 to 20 nmole/mg and is enhanced by the presence of divalent cations and the neutralization of the Tc/DNA solution. The photolytic production of bindable material is enhanced by the presence of oxygen and by the basicity of the photolysis solution.
Degree
Ph.D.
Subject Area
Organic chemistry
Off-Campus Purdue Users:
To access this dissertation, please log in to our
proxy server.