The ferrocene moiety as a structural probe: redox and structural properties of ferrocenoyl-oligoprolines Fc---Pron---OBzl (n=1-4) and Fc---Pro2---Phe---OBzl

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DOIResolve DOI: http://doi.org/10.1016/S0022-328X(99)00300-9
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TypeArticle
Journal titleJournal of Organometallic Chemistry
Volume589
Issue1
Pages3849; # of pages: 12
SubjectBioorganometallic; Crystal structure; Ferrocene; NMR; Oligopeptide; Proline; Redox behavior
AbstractThe preparations of the five ferrocenoyl-oligopeptides, Fc---Pro---OBzl (1), Fc---Pro2---OBzl (2), Fc---Pro3---OBzl (3), Fc---Pro4---OBzl (4) and Fc---Pro2---Phe---OBzl (5) are described. Crystallographic studies show that the Fc-oligoprolines 1-4 adopt a helical polyproline II structure having all prolines in a mutually trans-conformation. This structure is maintained in MeCN and CHCl3 solutions, as was shown by NMR methods. Chemical and magnetic similarities among the proline residues render spectral assignment by conventional 1D 1H-NMR spectroscopy impossible. However, a combination of 2D NMR techniques allowed us to unequivocally assign all signals. The redox potential of the Fc-group attached to the oligoproline chain is sensitive to the sequence and length of the oligopeptide. With growing peptide length, the molecule becomes easier to oxidize.
Publication date
AffiliationNational Research Council Canada; NRC Steacie Institute for Molecular Sciences; NRC Institute for Chemical Process and Environmental Technology
Peer reviewedNo
NPARC number12337151
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Record identifier1d8aee32-10d1-4c55-ba1a-ac73d684cf06
Record created2009-09-10
Record modified2016-05-09
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