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

• Published in: European Journal of Organic Chemistry 2009-05, Vol.2009 (13), p.2120-2129
• Main Authors: Sudhir, V. Sai, Venkateswarlu, Ch, Musthafa, O. T. Muhammed, Sampath, S., Chandrasekaran, Srinivasan
• Format: Article
• Language: English
• Subjects: Amino acids; Chemistry; Click chemistry; Cyclic voltammetry; Cyclo­addition; Exact sciences and technology; Ferrocenes; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Organic chemistry; Peptides; Preparations and properties
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.200801266

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.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) Ferrocene conjugates with amino acids were synthesized employing copper‐catalyzed 1,3‐dipolar cycloaddition. Ethynylferrocene and ferrocene‐derived azides were used for labeling. Diverse amino acidderived azides and alkynes were synthesized and labeled with ferrocene. A few conjugates were characterized by cyclic voltammetry.