Substrate screening for a novel condensation of imines: New approach towards a "click" type reaction for bioconjugation

• Main Author: Janairo, Jose Isagani B.
• Format: text
• Language: English
• Published: Animo Repository 2011
• Subjects: Imines; Bioconjugates; Condensation; Chemistry
• Online Access: https://animorepository.dlsu.edu.ph/etd_masteral/6626; https://animorepository.dlsu.edu.ph/cgi/viewcontent.cgi?article=12995&context=etd_masteral
• Institution: De La Salle University

An unprecedented condensation reaction of N-benzylimines was applied to the bioconjugation of lysine residues. A second-generation lysine dendrimer 14 with four ε-amino groups was prepared as the model peptide using solid-supported methods. The dendrimer 14 reacted with N-benzylimine 8 in DMF, which was readily obtained from fumaraldehydic acid methyl ester and benzylamine, to provide the corresponding 1,2 diazetidine derivatives at room temperature. The reaction might proceed through the conjugate addition of the lysine ε-amino groups to the α-β unsaturated ester of 8 followed by the condensation between the two imines. The novel reaction offers a promising “click” reaction for bioconjuation since it does not require any catalysts and proceeds under mild conditions.