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Click Chemistry Inspired Synthesis of Novel Ferrocenyl-Substituted Amino Acids or Peptides

Sudhir, V Sai and Venkateswarlu, Ch and Musthafa, OT Muhammed and Sampath, S and Chandrasekaran, Srinivasan (2009) Click Chemistry Inspired Synthesis of Novel Ferrocenyl-Substituted Amino Acids or Peptides. In: European Journal Of Organic Chemistry (13). pp. 2120-2129.

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This work reports on the synthesis of a wide range of ferrocenyl-substituted amino acids and peptides in excellent yield. Conjugation is established via copper-catalyzed 1,3-dipolar cycloaddition. Two complementary strategies were employed for conjugation, one involving cycloaddition of amino acid derived azides with ethynyl ferrocene 1 and the other involves cycloaddition between amino acid derived alkynes with ferrocene-derived azides 2 and 3. Labeling of amino acids at multiple sites with ferrocene is discussed. A new route to 1,1'-unsymmetrically substituted ferrocene conjugates is reported. A novel ferrocenophane 19 is accessed via bimolecular condensation of amino acid derived bis-alkyne 9b with the azide 2. The electrochemical behavior of some selected ferrocene conjugates has been studied by cyclic voltammetry.

Item Type: Journal Article
Publication: European Journal Of Organic Chemistry
Publisher: John Wiley and Sons Ltd
Additional Information: Copyright of this article belongs to John Wiley and Sons Ltd.
Keywords: Click chemistry;Amino acids;Ferrocenes;Cyclic voltammetry; Cycloaddition.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited: 28 May 2009 09:50
Last Modified: 19 Sep 2010 05:32
URI: http://eprints.iisc.ac.in/id/eprint/20429

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