N-Alkyl cysteine-assisted thioesterification of peptides

N-Alkyl cysteine at the C-terminus of peptides effectively promotes thioesterification by 3-mercaptopropionic acid. A new method for the preparation of peptide thioester by the post-solid phase peptide synthesis (SPPS) approach was developed. A series of N-alkyl cysteine derivatives were prepared an...

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Bibliographic Details
Published inTetrahedron letters Vol. 48; no. 1; pp. 25 - 28
Main Authors Hojo, Hironobu, Onuma, Yuko, Akimoto, Yuri, Nakahara, Yuko, Nakahara, Yoshiaki
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 2007
Elsevier
Subjects
Chemistry
Chemistry, Organic
Fmoc solid-phase method
N– S Acyl transfer
Peptide thioester
Physical Sciences
Science & Technology
Peptide thioester
Fmoc solid-phase method
N– S Acyl transfer
POLYPEPTIDE-SYNTHESIS
FMOC-BASED SYNTHESIS
IG DOMAIN
SOLID-PHASE SYNTHESIS
NATIVE CHEMICAL LIGATION
peptide thioester
S ACYL SHIFT
SUPPORT
C-TERMINAL THIOESTERS
EMMPRIN
PROTEINS
N-S acyl transfer
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Summary:N-Alkyl cysteine at the C-terminus of peptides effectively promotes thioesterification by 3-mercaptopropionic acid. A new method for the preparation of peptide thioester by the post-solid phase peptide synthesis (SPPS) approach was developed. A series of N-alkyl cysteine derivatives were prepared and used as the C-terminus residue of the peptides prepared by the Fmoc SPPS. The synthetic peptides released from resin by TFA were readily converted to the peptide thioester in aqueous 3-mercaptopropionic acid (MPA) without significant side reactions.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.11.034