Synthesis 2013; 45(8): 1099-1105
DOI: 10.1055/s-0032-1318486
paper
© Georg Thieme Verlag Stuttgart · New York

A Practical Protocol for the Conjugation of Various Amino Acids to Protoporphyrin IX

Ksenia Maximova
Institute of Organic Chemistry, PAS, Kasprzaka 44/52, 01-224 Warsaw, Poland   Fax: +48(22)6326681   Email: dorota.gryko@icho.edu.pl
,
Sabina Pisarek
Institute of Organic Chemistry, PAS, Kasprzaka 44/52, 01-224 Warsaw, Poland   Fax: +48(22)6326681   Email: dorota.gryko@icho.edu.pl
,
Dorota Gryko*
Institute of Organic Chemistry, PAS, Kasprzaka 44/52, 01-224 Warsaw, Poland   Fax: +48(22)6326681   Email: dorota.gryko@icho.edu.pl
› Author Affiliations
Further Information

Publication History

Received: 08 January 2013

Accepted after revision: 25 February 2013

Publication Date:
21 March 2013 (online)


Abstract

An effective and reliable method was developed for the synthesis of protoporphyrin IX-derived amides. The reaction of protoporphyrin IX with an amino acid [l-leucine, l-valine, l-lysine, l-aspartic acid (Asp), l-glutamic acid (Glu), glycine, or 6-aminohexanoic acid] or a short peptide (Asp-Glu) as an amine counterpart in the presence of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate and 1H-1,2,3-benzotriazol-1-ol gave the desired diamides in excellent yields.

Supporting Information