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Synlett 2016; 27(11): 1685-1688
DOI: 10.1055/s-0035-1561970
DOI: 10.1055/s-0035-1561970
letter
A Facile Synthesis of NODASA-Functionalized Peptide
Further Information
Publication History
Received: 28 January 2016
Accepted after revision: 07 March 2016
Publication Date:
30 March 2016 (online)
Abstract
Herein, we report a mild and efficient synthesis of a NODASA-functionalized peptide, which was initiated with a Michael addition reaction between monomethyl fumarate and 1,4,7-triazacyclononane.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561970.
- Supporting Information
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References and Notes
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- 15 General Procedure for the Synthesis of 1-Amino-2-benzyl-15-[4,7-bis(2-tert-butoxy-2-oxoethyl)-1,4,7-triazonan-1-yl]-11-(4-hydroxybenzyl)-1,4,7,10,13-pentaoxo-3,6,9,12-tetra-azahexadecan-16-oic Acid (5) The functionalized peptide on resin 4; 0.0125 mmol was swelled in 1.0 ml CH2Cl2 for 5 min followed by filtration, and 1.0 mL of 1 M LiOH (dissolved in MeOH and THF in 1:1 ratio) was added. The reaction was carried out for a period of 30 min at room temperature. The completion of the reaction was monitored by cleaving an aliquot of the compound from the resin and checked by LC–MS as well as analytical HPLC. The resin was washed with about 5.0 mL of THF (2×), DMF (2×), and CH2Cl2 (2×) consecutively. Compound 5 (0.0125 mmol) was deprotected and cleaved from the resin using a cocktail of 1.0 mL TFA/H2O/thioanisole (95:2.5:2.5) over 2 h. The resin was removed by filtration and washed with 1 mL TFA. Further, TFA was evaporated with the aid of N2 gas bubbling through the mixture. The peptide was then precipitated in 5.0 mL of ice-cold Et2O. The precipitated peptide was centrifuged and the Et2O solution was decanted. It was then dissolved in 1.0 mL of water and freeze dried without further purification which gave a yield of 84%. The purity of the synthesis was checked by analytical RP-HPLC which showed 100% purity and characterized by LC–MS. HRMS (ESI+): m/z calcd. for C36H49N8O12 [M + H]: 785.3464; found: 785.3434