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Synthesis of Spirobicyclic Peptides on a Solid Support
Author(s) -
Virta Pasi,
Sinkkonen Jari,
Lönnberg Harri
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200211)2002:21<3616::aid-ejoc3616>3.0.co;2-j
Subject(s) - chemistry , linker , branching (polymer chemistry) , amide , peptide synthesis , solid phase synthesis , peptide , combinatorial chemistry , malonic acid , stereochemistry , block (permutation group theory) , organic chemistry , biochemistry , geometry , mathematics , computer science , operating system
The spirobicyclic peptides 2 − 6 were synthesized as stereoisomeric pairs using an orthogonally protected bis(aminomethyl)malonic acid building block 1 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 .