| Title: |
Cysteine-Free Intramolecular Ligation of N-Sulfanylethylanilide Peptide Using 4-Mercaptobenzylphosphonic Acid: Synthesis of Cyclic Peptide Trichamide. |
| Authors: |
Keisuke Aihara, Tsubasa Inokuma, Takahisa Jichu, Zhenjian Lin, Feixue Fu, Kosuke Yamaoka, Akira Shigenaga, Hutchins, David A., Schmidt, Eric W., Akira Otaka |
| Source: |
Synlett; 2017, Vol. 28 Issue 15, p1944-1949, 6p |
| Subject Terms: |
CYSTEINE, LIGATION reactions, PHOSPHONIC acids |
| Abstract: |
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. [ABSTRACT FROM AUTHOR] |
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| Database: |
Complementary Index |
