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ID 111889
タイトル別表記
Cysteine-free Intramolecular Ligation of N-Sulfanylethylanilide Peptide Using 4-Mercaptobenzylphosphonic Acid : Synthesis of Cyclic Peptide, Trichamide
著者
Aihara, Keisuke Tokushima University
Jichu, Takahisa Tokushima University
Lin, Zhenjian University of Utah
Fu, Feixue University of Southern California
Yamaoka, Kosuke Tokushima University
Hutchins, David A. University of Southern California
Schmidt, Eric W. University of Utah
キーワード
peptides
thioester
N-S acyl transfer
chemical ligation
cyclic peptides
資料タイプ
学術雑誌論文
抄録
An N-sulfanylethylanilide (SEAlide)-based ligation was developed for the preparation of trichamide, a thiazole-containing cyclic peptide isolated from bloom-forming cyanobacterium Trichodesmium erythraeum. In this cysteine-free ligation, 4-mercaptobenzylphosphonic acid (MBPA) functions as a dual promoter both for the N–S acyl-transfer-mediated activation of the SEAlide unit and for subsequent ligation. Furthermore, we established a high-yielding route to enantiomerically pure thiazole amino acids using a one-pot Hantzsch process.
掲載誌名
Synlett
ISSN
09365214
14372096
cat書誌ID
AA10731110
AA12357740
出版者
Thieme
28
15
開始ページ
1944
終了ページ
1949
発行日
2017-07-06
権利情報
© Georg Thieme Verlag Stuttgart · New York
EDB ID
出版社版DOI
出版社版URL
フルテキストファイル
言語
eng
著者版フラグ
著者版
部局
薬学系