A1 Refereed original research article in a scientific journal
Synthesis of spirobicyclic peptides on a solid support
Authors: Virta P, Sinkkonen J, Lonnberg H
Publisher: WILEY-V C H VERLAG GMBH
Publication year: 2002
Journal:: European Journal of Organic Chemistry
Journal name in source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Journal acronym: EUR J ORG CHEM
Volume: 2002
Issue: 21
First page : 3616
Last page: 3621
Number of pages: 6
ISSN: 1434-193X
DOI: https://doi.org/10.1002/1099-0690(200211)2002:21<3616::AID-EJOC3616>3.0.CO;2-J
Abstract
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.
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.
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