Peptide ligation using a building block having a Cysteinyl Prolyl Ester (CPE) autoactivating unit at the carboxy terminus

Chemistry Letters

Volumn 36, Issue 1, 2007, Pages 76-77

  Kawakami, Toru ^a   Aimoto, Saburo ^a  

^a OSAKA UNIVERSITY   (Japan)

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Indexed keywords

EID: 33846935794     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.76     Document Type: Article

References (19)

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12. An attempt to produce a peptide thioester by using a 5- mercaptomethylprolyl prolyl ester derivative via DKP formation was recently reported, but failed. The thioester was produced by the treatment of a 5-mercaptomethylprolyl amide derivative with 3-mercaptopropionic acid under microwave conditions. F. Nagaike, Y. Onuma, C. Kanazawa, H. Hojo, A. Ueki, Y. Nakahara, Y. Nakahara, Org. Lett. 2006, 8, 4465.
13. Peptide ligation via N-S acyl shift reaction at an active imide position was recently reported, but the building block cannot be prepared by standard Fmoc SPPS. Y. Ohta, S. Itoh, A. Shigenaga, S. Shintaku, N. Fuji, A. Otaka, Org. Lett. 2006, 8, 467.
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19. 8b Therefore, decomposition of the CPE peptide might be negligible during TFA or HF treatment in which the DKP is not formed under the acidic conditions.