A1 Vertaisarvioitu alkuperäisartikkeli tieteellisessä lehdessä
Synthesis of spirobicyclic peptides on a solid support
Tekijät: Virta P, Sinkkonen J, Lonnberg H
Kustantaja: WILEY-V C H VERLAG GMBH
Julkaisuvuosi: 2002
Lehti:: European Journal of Organic Chemistry
Tietokannassa oleva lehden nimi: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Lehden akronyymi: EUR J ORG CHEM
Vuosikerta: 2002
Numero: 21
Aloitussivu: 3616
Lopetussivu: 3621
Sivujen määrä: 6
ISSN: 1434-193X
DOI: https://doi.org/10.1002/1099-0690(200211)2002:21<3616::AID-EJOC3616>3.0.CO;2-J
Tiivistelmä
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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