Metal-Dependent Intramolecular Chiral Induction: The Zn^(2+) Complex of an Ethidium−Peptide Conjugate
Abstract
Ethidium bromide is an aromatic organic dye that for many years has been known to bind via intercalation to the minor groove of DNA. When the ethidium cation binds to DNA, the chirality of the right-handed double helix is imposed upon ethidium (Et), producing induced circular dichroism (ICD). Other examples of ICD have been observed in the heme group of hemoglobin and myoglobin as well as synthetic porphyrin assemblies, and in host−guest assemblies. In every case, an ICD spectrum is produced as a result of the close association of an achiral chromophore with a chiral moiety (e.g., a biopolymer). During the course of our ongoing research into artificial hydrolytic nucleases, we prepared an ethidium−peptide conjugate that displays metal-dependent ICD. Here we report the synthesis and spectroscopic characterization of a metal−peptide assembly which may represent a first example of metal-dependent intramolecular chiral induction.
Additional Information
© 1999 American Chemical Society. Received August 21, 1998. We are grateful to the NSF (CHE9530476) for financial support of this work. R.P.H. thanks the NIH for a NRSA postdoctoral fellowship (GM18646-02). Additionally we thank the Biopolymer Synthesis and Analysis Center at Caltech and the City of Hope Division of Immunology for their technical support.Attached Files
Supplemental Material - ic981012c_s.pdf
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Additional details
- Eprint ID
- 65987
- Resolver ID
- CaltechAUTHORS:20160407-115522678
- NSF
- CHE9530476
- NIH Predoctoral Fellowship
- GM18646-02
- Created
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2016-04-08Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field