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Synlett 2017; 28(15): 1944-1949
DOI: 10.1055/s-0036-1589055
DOI: 10.1055/s-0036-1589055
cluster
Cysteine-Free Intramolecular Ligation of N-Sulfanylethylanilide Peptide Using 4-Mercaptobenzylphosphonic Acid: Synthesis of Cyclic Peptide Trichamide
This research was supported in part by a Grant-in-Aid for Scientific Research (KAKENHI). K.A. is grateful for a JSPS fellowship (14J07568). T.J. is grateful for SUNBOR SCHOLARSHIP.Further Information
Publication History
Received: 24 April 2017
Accepted after revision: 24 May 2017
Publication Date:
06 July 2017 (online)
Published as part of the Cluster Recent Advances in Protein and Peptide Synthesis
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1589055.
- Supporting Information
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- 16 SEAlide peptide 19 (5.2 mg, 3.0 μmol) was dissolved in 6.0 mL of degassed ligation buffer (NMP/H2O = 4:1 (v/v) containing 20 mM MBPA, 15 mM TCEP·HCl, final pH 7.6), and the reaction mixture was incubated at 37 °C. After 72 h, the mixture was diluted with 0.1% aq TFA, and the product was purified by preparative HPLC to give trichamide 3 as a white lyophilized powder (2.5 mg, 1.9 μmol, 63%). Preparative HPLC Conditions Cosmosil 5C18-AR-II preparative column (20 × 250 mm, flow rate 10.0 mL/min) with a linear gradient of solvent B/solvent A (20:80 to 30:70 over 30 min). Analytical HPLC Conditions Cosmosil 5C18-AR-II analytical column (4.6 × 250 mm, flow rate 1.0 mL/min) with a linear gradient of solvent B/solvent A [10:90 to 55:45 over 30 min (curve 7 of the Waters 600E)], t R = 22.4 min. HRMS (ESI-TOF): m/z calcd for C46H66N16O12S2 [M + H]+: 1099.4566; found: 1099.4569.