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Metal-Dependent Intramolecular Chiral Induction: The Zn^(2+) Complex of an Ethidium−Peptide Conjugate

Houser, Robert P. and Fitzsimons, Marilena P. and Barton, Jacqueline K. (1999) Metal-Dependent Intramolecular Chiral Induction: The Zn^(2+) Complex of an Ethidium−Peptide Conjugate. Inorganic Chemistry, 38 (6). pp. 1368-1370. ISSN 0020-1669. doi:10.1021/ic981012c. https://resolver.caltech.edu/CaltechAUTHORS:20160407-115522678

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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.


Item Type:Article
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URLURL TypeDescription
http://dx.doi.org/10.1021/ic981012cDOIArticle
http://pubs.acs.org/doi/full/10.1021/ic981012cPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ic981012cRelated ItemSupporting Information
ORCID:
AuthorORCID
Barton, Jacqueline K.0000-0001-9883-1600
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.
Funders:
Funding AgencyGrant Number
NSFCHE9530476
NIH Predoctoral FellowshipGM18646-02
Issue or Number:6
DOI:10.1021/ic981012c
Record Number:CaltechAUTHORS:20160407-115522678
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20160407-115522678
Official Citation:Metal-Dependent Intramolecular Chiral Induction:  The Zn2+ Complex of an Ethidium−Peptide Conjugate Robert P. Houser,Marilena P. Fitzsimons,, and Jacqueline K. Barton Inorganic Chemistry 1999 38 (6), 1368-1370 DOI: 10.1021/ic981012
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:65987
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:08 Apr 2016 16:06
Last Modified:10 Nov 2021 23:51

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