Amino acid bromides: their utilization for difficult couplings in solid-phase peptide synthesis

Use of N-protected-α-amino acid bromides for facile solid-phase synthesis of peptides (SPPS) containing extremely sterically hindered non-proteinogenic amino acids is presented. Amino acid bromides (Aaa-Br), generated in situ, were used for the synthesis of long chain homopeptides containing up to e...

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Bibliographic Details
Published in:Tetrahedron letters 2005-09, Vol.46 (37), p.6369-6371
Main Authors: Ni, Minghong, Esposito, Emiliano, Kaptein, Bernard, Broxterman, Quirinus B., Dal Pozzo, Alma
Format: Article
Language:English
Subjects:
Amino acid bromides
Difficult couplings
Solid-phase peptide synthesis
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Summary:Use of N-protected-α-amino acid bromides for facile solid-phase synthesis of peptides (SPPS) containing extremely sterically hindered non-proteinogenic amino acids is presented. Amino acid bromides (Aaa-Br), generated in situ, were used for the synthesis of long chain homopeptides containing up to eight successive α-MeVal or Aib residues. SPPS of a heteropeptide containing a very bulky amino acid building block is also described. The choice of suitable N-protections is discussed.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.07.017