Manual Solid–Phase Peptide Synthesis of Metallocene–Peptide Bioconjugates

Srecko I. Kirin , Fozia Noor and Nils Metzler-Nolte
Institute of Pharmacy and Molecular Biotechnology, University of Heidelberg, D-69120 Heidelberg, Germany
Walter Mier
Department of Nuclear Medicine, University Hospital Heidelberg, D-69120 Heidelberg, Germany
J. Chem. Educ., 2007, 84 (1), p 108
DOI: 10.1021/ed084p108
Publication Date (Web): January 1, 2007

Abstract

We describe a simple procedure for the manual solid-phase synthesis of peptides. No expensive or specialized equipment is needed. Moreover, a variety of markers can be attached to the N-terminus. We describe two organometallic markers and a fluroescent dye, in addition to an unlabeled derivative that serves as a comparison. The experiment described herein was successfully carried out by fourth-year undergraduate students of molecular biotechnology. By carrying out this experiment, the students gained first-hand experience for one of the most important modern synthesis techniques.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Biochemistry

Keywords (Subject):

Bioorganic Chemistry

Citing Articles

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This article has been cited by 4 ACS Journal articles (4 most recent appear below).

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      The facile and direct reaction of alkynes with Co2(CO)8 yields Co2(alkyne)(CO)6 derivatives of several classes of biomolecules quantitatively. By incorporation of the alkyne during solid phase peptide synthesis (SPPS), the site of labeling with the ...

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    Peptide-Based SAMs that Resist the Adsorption of Proteins

    Rolf Chelmowski, Stephan David Köster, Andreas Kerstan, Andreas Prekelt, Christian Grunwald, Tobias Winkler, Nils Metzler-Nolte, Andreas Terfort and Christof Wöll
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    • Peptide-Based SAMs that Resist the Adsorption of Proteins

      Rolf Chelmowski, Stephan David Köster, Andreas Kerstan, Andreas Prekelt, Christian Grunwald, Tobias Winkler, Nils Metzler-Nolte, Andreas Terfort and Christof Wöll
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      In this paper we present a modular approach for the fabrication of surfaces to characterize protein−protein interactions. The approach is based on azido peptides with an optimized sequence which are then thiol-functionalized using an alkynyl thiol and “...

  • Cover Image

    Labeling of the Neuropeptide Enkephalin with Functionalized Tris(pyrazolyl)borate Complexes:  Solid-Phase Synthesis and Characterization of p-[Enk-OH]COC6H4TpPtMe3 and p-[Enk-OH]COC6H4TpMeRe(CO)3

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    • Labeling of the Neuropeptide Enkephalin with Functionalized Tris(pyrazolyl)borate Complexes:  Solid-Phase Synthesis and Characterization of p-[Enk-OH]COC6H4TpPtMe3 and p-[Enk-OH]COC6H4TpMeRe(CO)3

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      Inorganic Chemistry2007 46 (22), 9400-9404

      Bioconjugates of the neuropeptide Enkephalin (Enk = −Tyr−Gly−Gly−Phe−Leu−) labeled with organotransition metal tris-pyrazolylborate (Tp) complexes are reported. p-[Enk-OH]COC6H4TpPtMe3 and p-[Enk-OH]COC6H4TpMeRe(CO)3 have been synthesized by solid-phase ...

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History

  • Received: August 03, 2009

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