Synthesis of spirobicyclic peptides on a solid support



: Virta P, Sinkkonen J, Lonnberg H

Publisher: WILEY-V C H VERLAG GMBH

: 2002

: European Journal of Organic Chemistry

: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

: EUR J ORG CHEM

: 2002

: 21

: 3616

: 3621

: 6

: 1434-193X

DOI: https://doi.org/10.1002/1099-0690(200211)2002:21<3616::AID-EJOC3616>3.0.CO;2-J


The spirobicyclic peptides 2-6 were synthesized as stereoisomeric pairs using an orthogonally protected bis(aminomethyl)malonic acid building block I as the branching unit. Peptide 2 was synthesized by two methods. Either the chain assembly and first cyclization were carried out on a Wang resin, and the second cyclization in solution (Scheme 1), or the whole synthesis was performed on a solid-supported backbone amide linker derived from 4-alkoxybenzaldehyde (Scheme 3). The applicability of the latter method was further evaluated by synthesis of four additional spirobicyclic peptides 3-6.



Last updated on 2025-13-10 at 14:47