Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2013; 45(8): 1099-1105
DOI: 10.1055/s-0032-1318486
DOI: 10.1055/s-0032-1318486
paper
A Practical Protocol for the Conjugation of Various Amino Acids to Protoporphyrin IX
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
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Berg JM, Tymoczko JL, Stryer L. Biochemistry . 6th ed. W. H. Freeman; New York: 2007
- 1b Schwartz HC, Goudsmit R, Hill RL, Cartwright GE, Wintrobe MM. J. Clin. Invest. 1961; 40: 188
- 1c Montforts F.-P, Gerlach B, Höper F. Chem. Rev. 1994; 94: 327
- 2a Sibrian-Vazquez M, Hu X, Jensen TJ, Vicente MG. H. J. Porphyrins Phthalocyanines 2012; 16: 603
- 2b Evstigneeva RP, Zarubina TV, Zheltukhina GA, Nebol’sin VE, Kaliberda EN, Rumsh LD. Dokl. Chem. (Engl. Transl.) 2001; 381: 349
- 2c Sol V, Lamarche F, Enache M, Garcia G, Granet R, Guilloton M, Blais JC, Krausz P. Bioorg. Med. Chem. 2006; 14: 1364
- 3a Ignarro LJ, Wood KS, Wolin MS. Proc. Natl. Acad. Sci. U.S.A. 1982; 79: 2870
- 3b Wolin MS, Wood KS, Ignarro LJ. J. Biol. Chem. 1982; 257: 13312
- 3c Ignarro LJ, Ballot B, Wood KS. J. Biol. Chem. 1984; 259: 6201
- 4a Pavlov VYu. Russ. J. Org. Chem. (Engl. Transl.) 2007; 43: 9
- 4b Shanmugathasan S, Edwards C, Boyle RW. Tetrahedron 2000; 56: 1025
- 4c Razzaque MA, Lord GA, Lim CK. Rapid Commun. Mass Spectrom. 2002; 16: 1675
- 4d Giuntini F, Alonso CM. A, Boyle RW. Photochem. Photobiol. Sci. 2011; 10: 759
- 5 Doss M, Ulshöfer B. Biochim. Biophys. Acta 1971; 237: 356
- 6a Montalbetti CA. G. N, Falque V. Tetrahedron 2005; 61: 10827
- 6b Bode JW. Curr. Opin. Drug Discovery Dev. 2006; 9: 765
- 7 Matsuo T, Nagai H, Hisaeda Y, Hayashi T. Chem. Commun. (Cambridge) 2006; 3131
- 8 Bhosale SV, Kalyankar MB, Nalage SV, Bhosale SV, Lalander CH, Langford SJ. Supramol. Chem. 2011; 23: 563
- 9 Bhosale SV, Bhosale SV, Kalyankar MB, Langford SJ, Lalander CH. Aust. J. Chem. 2010; 63: 1326
- 10 Raduhin VA, Philippovich EI, Evstigneeva RP. Zh. Org. Khim. 1979; 50: 673
- 11a Molokoedov AS, Philippovich EI, Kazakova NA, Evstigneeva RP. Zh. Org. Khim. 1975; 47: 1165
- 11b Pispisa B, Venanzi M, Palleschi A, Zanotti G. Macromolecules 1994; 27: 7800
- 11c Traylor TG, Chang CK, Geibel J, Berzinis A, Mincey T, Cannon J. J. Am. Chem. Soc. 1979; 101: 6716
- 11d Van der Heijden A, Peer HG, Van der Oord AH. A. Chem. Commun. (Cambridge) 1971; 369
- 11e Pispisa B, Venanzi M, Stella L, Palleschi A, Zanotti G. J. Phys. Chem. B 1999; 103: 8172
- 12 Liang G, Wang L, Yang Zh, Koon H, Mak N, Chang CK, Xu B. Chem. Commun. (Cambridge) 2006; 5021
- 13 Nakagawa A, Ohmichi N, Komatsu T, Tsuchida E. Org. Biomol. Chem. 2004; 2: 3108
- 14 Gershokvich AA, Kibirev VK. Sintez Peptidov: Reagenty i Metody. Naukova Dumka; Kiev: 1987
- 15 Tully DC, Chatterjee AK, Wang Z. WO 2008097676, 2008
- 16 Feichtinger K, Sings HL, Baker TJ, Matthews K, Goodman M. J. Org. Chem. 1998; 63: 8432