Journal
TETRAHEDRON
Volume 60, Issue 44, Pages 10049-10058Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2004.07.057
Keywords
porphyrin-steroid conjugate; catalytic antibodies; artificial metalloprotein
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We here report the synthesis of a novel porphyrin-steroid conjugate which was designed for the site-specific incorporation of a non-natural heme cofactor at the binding site of an anti-estradiol antibody, in order to get a semi-synthetic catalytic antibody with a monooxygenase-like activity. The general strategy involved a coupling reaction between a testosterone modified by an arm bearing a cleavable disulfide bridge and a meso-tetraarylporphyrin bearing two successive meso-ortho-substituted-phenyl rings, alpha,alpha-5,10-bis-[{o-(2-carboxyethyl)carboxamido}phenyl]-15,20-diphenyl-porphyrin. The final porphyrin-steroid conjugate was successfully purified and fully characterized, and was subsequently metalated with manganese acetate. The metalloporphyrin moiety will be used to be coupled with the antibody to generate a new biocatalyst with monooxygenase-like activities. (C) 2004 Elsevier Ltd. All rights reserved.
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