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Synfacts 2010(11): 1311-1311  
DOI: 10.1055/s-0030-1258829
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

1,3-Dipolar Cycloaddition of Aza-Propargylglycine with Aryl Azides

Contributor(s): Yasuhiro Uozumi, Aya Tazawa
C. Proulx, W. D. Lubell*
Université de Montréal, Canada
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Publication History

Publication Date:
21 October 2010 (online)

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Significance

An aza-propargylglycine residue immobilized onto rink amide peptide 1 was treated with aryl iodides, NaN3, and CuI in the presence of l-proline to give the corresponding aza-1,2,3-triazole-4-alanine residues 2 in 58-82% conversion. After removal of N-benzylidene, the resulting azapeptides 3 were elongated and deprotected to give analogues of [aza-1,2,3-triazole-4-alanine4] growth hormone releasing peptide-6 (GHRP-6) 4 in 5-11% overall yields based on initial resin loading.