Synthesis of the Backbone Cyclic Peptide Sunflower Trypsin Inhibitor-1 Promoted by the Induced Peptidyl-tRNA Drop-off

Synthesis of the Backbone Cyclic Peptide Sunflower Trypsin Inhibitor-1 Promoted by the Induced Peptidyl-tRNA Drop-off

Shifting around: A rapid one‐pot preparation of a backbone cyclic peptide from peptidyl‐tRNA, which has been ejected from the ribosome is described. A series of intramolecular rearrangements release tRNA and afford 1. A cyclization gives 2 and on enzymatic removal of the formylated methionine (fM) t...

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Veröffentlicht in:Angewandte Chemie International Edition 2011-02, Vol.50 (9), p.2159-2161
Hauptverfasser: Kang, Taek Jin, Hayashi, Yuuki, Suga, Hiroaki
Format: Artikel
Sprache:eng
Schlagworte:
Amidohydrolases - metabolism
Amino Acid Sequence
amino acids
Aminopeptidases - metabolism
Cyclization
Methionyl Aminopeptidases
Molecular Sequence Data
peptide ligation
peptides
Peptides, Cyclic - biosynthesis
Peptides, Cyclic - chemistry
RNA, Transfer, Amino Acyl - chemistry
RNA, Transfer, Amino Acyl - metabolism
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
tRNA
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Zusammenfassung:Shifting around: A rapid one‐pot preparation of a backbone cyclic peptide from peptidyl‐tRNA, which has been ejected from the ribosome is described. A series of intramolecular rearrangements release tRNA and afford 1. A cyclization gives 2 and on enzymatic removal of the formylated methionine (fM) the backbone cyclic peptide is generated.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201006963