Facile, Fmoc-compatible solid-phase synthesis of peptide C-terminal thioesters

Organic Letters

Volumn 2, Issue 16, 2000, Pages 2439-2442

  Swinnen, Dominique ^a,b   Hilvert, Donald ^b  

^a SERONO PHARMACEUTICAL RES INSTITUTE   (Switzerland)

^b ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ESTER; OLIGOPEPTIDE; PEPTIDE; THIOL DERIVATIVE;

AMINO ACID SEQUENCE; ARTICLE; CHEMISTRY; MOLECULAR GENETICS; SYNTHESIS;

AMINO ACID SEQUENCE; ESTERS; INDICATORS AND REAGENTS; MOLECULAR SEQUENCE DATA; OLIGOPEPTIDES; PEPTIDES; SULFHYDRYL COMPOUNDS;

EID: 0034632429     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0060836     Document Type: Article

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33. Asp-Gly and Asp-Asp are known to be problematic motifs prone to aspartimide formation (Quibell, M.; Owen, D.; Packman, L. C.; Johnson, T. J. Chem. Soc., Chem. Commun. 1994, 2343-2344). In this particular reaction, the aspartimide peptide thioester generated by cyclization of the aspartyl residue during the cleavage reaction is the major product [50% of the total peptide material as judged by integration of HPLC chromatograms and electrospray mass spectrometry (ESMS)].
34. To suppress the formation of side products (aspartimide and bisthioester), THF (20 equiv) was added as a weak Lewis base to coordinate the aluminum reagent. This modification reduced the amount of aspartamide side product formed (only 11% of the total peptide material, as determined by HPLC) and increased the overall yield of thioester 5c up to 37%, but the formation of bis-thioester 7c was also enhanced somewhat (20%).
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