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Synthesis and structure analysis of ferrocene‐containing pseudopeptides

Synthesis and structure analysis of ferrocene‐containing pseudopeptides Ferrocene with its aromaticity and facile redox properties is an attractive moiety to be incorporated into functional moieties. Medicinal applications of ferrocene are well known and ferrocene itself shows cytotoxic and antianemic properties. In this article, we will describe the synthesis and the structure analysis of two pseudopeptides containing a ferrocene moiety as N‐terminal group. After purification, Fc‐l‐Phe‐d‐Oxd‐OBn [l‐Phel‐phenylalanine; d‐Oxd(4R,5S)‐4‐Methyl‐5‐carboxy‐oxazolidin‐2‐one] appears as bright brown solid that spontaneously forms brown needles. The X‐ray diffraction of the crystals shows the presence of strong π interactions between the ferrocenyl moiety and the phenyl rings, while no NH•••OC hydrogen bonds are formed. This result is confirmed by FT‐IR and 1H NMR analysis. In contrast, both FT‐IR and 1H NMR analysis suggest that Fc‐(l‐Phe‐d‐Oxd)2‐OBn forms a turn conformation stabilized by intramolecular NH•••OC hydrogen bonds in solution. Chiroptical spectroscopies (ECD and VCD) substantially confirmed the absence of a well‐defined folded structure. The presence of the Fc moiety is responsible for specific ECD signals, one of which displayed pronounced temperature dependence and is directly related with the helicity assumed by the Fc core. Solid‐state ECD spectra were recorded and rationalized on the basis of the X‐ray geometry and quantum‐mechanical calculations. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Peptide Science Wiley

Synthesis and structure analysis of ferrocene‐containing pseudopeptides

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References (67)

Publisher
Wiley
Copyright
© 2018 Wiley Periodicals, Inc.
eISSN
2475-8817
DOI
10.1002/bip.23072
Publisher site
See Article on Publisher Site

Abstract

Ferrocene with its aromaticity and facile redox properties is an attractive moiety to be incorporated into functional moieties. Medicinal applications of ferrocene are well known and ferrocene itself shows cytotoxic and antianemic properties. In this article, we will describe the synthesis and the structure analysis of two pseudopeptides containing a ferrocene moiety as N‐terminal group. After purification, Fc‐l‐Phe‐d‐Oxd‐OBn [l‐Phel‐phenylalanine; d‐Oxd(4R,5S)‐4‐Methyl‐5‐carboxy‐oxazolidin‐2‐one] appears as bright brown solid that spontaneously forms brown needles. The X‐ray diffraction of the crystals shows the presence of strong π interactions between the ferrocenyl moiety and the phenyl rings, while no NH•••OC hydrogen bonds are formed. This result is confirmed by FT‐IR and 1H NMR analysis. In contrast, both FT‐IR and 1H NMR analysis suggest that Fc‐(l‐Phe‐d‐Oxd)2‐OBn forms a turn conformation stabilized by intramolecular NH•••OC hydrogen bonds in solution. Chiroptical spectroscopies (ECD and VCD) substantially confirmed the absence of a well‐defined folded structure. The presence of the Fc moiety is responsible for specific ECD signals, one of which displayed pronounced temperature dependence and is directly related with the helicity assumed by the Fc core. Solid‐state ECD spectra were recorded and rationalized on the basis of the X‐ray geometry and quantum‐mechanical calculations.

Journal

Peptide ScienceWiley

Published: Sep 1, 2018

Keywords: ; ; ;

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