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