| ID | 111889 |
| Title Alternative | Cysteine-free Intramolecular Ligation of N-Sulfanylethylanilide Peptide Using 4-Mercaptobenzylphosphonic Acid : Synthesis of Cyclic Peptide, Trichamide
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| Author |
Aihara, Keisuke
Tokushima University
Inokuma, Tsubasa
Tokushima University
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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
Otaka, Akira
Tokushima University
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|
| Keywords | peptides
thioester
N-S acyl transfer
chemical ligation
cyclic peptides
|
| Content Type |
Journal Article
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| Description | 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.
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| Journal Title |
Synlett
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| ISSN | 09365214
14372096
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| NCID | AA10731110
AA12357740
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| Publisher | Thieme
|
| Volume | 28
|
| Issue | 15
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| Start Page | 1944
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| End Page | 1949
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| Published Date | 2017-07-06
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| Rights | © Georg Thieme Verlag Stuttgart · New York
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| EDB ID | |
| DOI (Published Version) | |
| URL ( Publisher's Version ) | |
| FullText File | |
| language |
eng
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| TextVersion |
Author
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| departments |
Pharmaceutical Sciences
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