title: Applications of propargyl esters of amino acids in solution-phase Peptide synthesis.
abstract: Propargyl esters are employed as effective protecting groups for the carboxyl group during solution-phase peptide synthesis. The propargyl ester groups can be introduced onto free amino acids by treating them with propargyl alcohol saturated with HCl. The reaction between propargyl groups and tetrathiomolybdate is exploited to deblock the propargyl esters. The removal of the propargyl group with the neutral reagent tetrathiomolybdate ensures that most of the other protecting groups used in peptide synthesis are untouched. Both acid labile and base labile protecting groups can be removed in the presence of a propargyl ester. Amino acids protected as propargyl esters are employed to synthesize di- to tetrapeptides in solution-phase demonstrating the possible synthetic utilities of the methodology. The methodology described here could be a valuable addition to currently available strategies for peptide synthesis.
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
authors.forename: Ramesh
authors.initials: R
authors.lastname: Ramapanicker
authors.forename: Rohit
authors.initials: R
authors.lastname: Gupta
authors.forename: Rajendran
authors.initials: R
authors.lastname: Megha
authors.forename: Srinivasan
authors.initials: S
authors.lastname: Chandrasekaran