Journal
MOLECULES
Volume 27, Issue 9, Pages -Publisher
MDPI
DOI: 10.3390/molecules27092788
Keywords
green chemistry; ester hydrolysis; Fmoc; amino acid; solid-phase synthesis; medicinal chemistry
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This study systematically explored mild orthogonal ester hydrolysis conditions using calcium(II) iodide as a protective agent, providing a solution for selective deprotection of amino esters for SPPS-ready amino acids.
In order to modify amino acids, the C-terminus carboxylic acid usually needs to be protected, typically as a methyl ester. However, standard cleavage of methyl esters requires either highly basic or acidic conditions, which are not compatible with Fmoc or acid-labile protecting groups. This highlights the need for orthogonal conditions that permit selective deprotection of esters to create SPPS-ready amino acids. Herein, mild orthogonal ester hydrolysis conditions are systematically explored using calcium(II) iodide as a protective agent for the Fmoc protecting group and optimized for a broad scope of amino esters. Our optimized reaction improved on the already known trimethyltin hydroxide, as it produced better yields with greener, inexpensive chemicals and a less extensive energy expenditure.
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