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Synthesis 2017; 49(10): 2187-2204
DOI: 10.1055/s-0036-1588698
DOI: 10.1055/s-0036-1588698
paper
Fluorous Mixture Synthesis of Tripeptides and Pentapeptides Using a Fluorous-Fmoc Protection Strategy
Further Information
Publication History
Received: 28 November 2016
Accepted after revision: 05 January 2017
Publication Date:
06 February 2017 (online)
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Abstract
A liquid-phase split-type synthesis of various tripeptides and pentapeptides was conducted using a fluorous-Fmoc protection strategy. Fluorous-Fmoc reagents were effectively used as both the protecting group for the amino function and the encoding tag for the amino acid structure. Several of the synthetic peptides prepared showed high activities in an ACE inhibitory assay.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588698.
- Supporting Information
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References
- 1a Kent SB. H. Chem. Soc. Rev. 2009; 38: 338
- 1b Gallop MA, Barrett RW, Dower WJ, Fodor SP. A, Gordon EM. J. Med. Chem. 1994; 37: 1233
- 1c Terrett NK, Gardner M, Gordon DW, Kobylecki RJ, Steele J. Tetrahedron 1995; 51: 8135
- 1d Guillier F, Orain D, Bradley M. Chem. Rev. 2000; 100: 2091
- 2 Luo Z, Zhang Q, Oderaotoshi Y, Curran DP. Science 2001; 291: 1766
- 3a Curran DP, Oderaotoshi Y. Tetrahedron 2001; 57: 5243
- 3b Zhang Q, Rivkin A, Curran DP. J. Am. Chem. Soc. 2002; 124: 5774
- 3c Zhang W. Tetrahedron 2003; 59: 4475
- 3d Yang F, Newsome JJ, Curran DP. J. Am. Chem. Soc. 2006; 128: 14200
- 3e Zhang W. ARKIVOC 2004; (i): 101
- 3f Jung WH, Guyenne G, Riesco-Fagundo C, Mancuso J, Nakamura S, Curran DP. Angew. Chem. Int. Ed. 2008; 47: 1130
- 3g Zhang W In Fluorine in Medicinal Chemistry and Chemical Biology . Ojima I. Wiley-Blackwell; Hoboken: 2009: 335
- 3h Zhang K, Gudipati V, Curran DP. Synlett 2010; 667
- 3i Sui B, Yeh EA.-H, Curran DP. J. Org. Chem. 2010; 75: 2942
- 3j Bajpai R, Curran DP. J. Am. Chem. Soc. 2011; 133: 20435
- 3k Moretti JD, Wang X, Curran DP. J. Am. Chem. Soc. 2012; 134: 7963
- 3l Curran DP, Sinha MK, Zhang K, Sabatini JJ, Cho D.-H. Nat. Chem. 2012; 4: 124
- 3m Yeh EA.-H, Kumli E, Damodaran K, Curran DP. J. Am. Chem. Soc. 2013; 135: 1577
- 3n Sugiyama Y, Eguchi F, Miyazaki A, Hayashi K, Takahashi H, Hamamoto H, Shioiri T, Matsugi M. J. Org. Chem. 2013; 78: 10264
- 4a Matsugi M, Yamanaka K, Inomata I, Takekoshi N, Hasegawa M, Curran DP. QSAR Comb. Sci. 2006; 25: 713
- 4b Sugiyama Y, Ishihara K, Masuda Y, Kobayashi Y, Hamamoto H, Matsugi M. Tetrahedron Lett. 2013; 54: 2060
- 4c Sugiyama Y, Endo N, Ishihara K, Kobayashi Y, Hamamoto H, Shioiri T, Matsugi M. Tetrahedron 2015; 71: 4958
- 4d Wuts PG. M. Green’s Protective Groups in Organic Synthesis . 5th ed. John Wiley & Sons; Hoboken: 2014: 918
- 5 Sugiyama Y, Hirose M, Matsui J, Endo N, Hamamto H, Shioiri T, Matsugi M. Synlett 2013; 24: 2701
- 6a Goodman M, Levine L. J. Am. Chem. Soc. 1964; 86: 2918
- 6b Han S.-Y, Kim Y.-A. Tetrahedron 2004; 60: 2447
- 6c Montalbetti CA. G. N, Falque V. Tetrahedron 2005; 61: 10827
- 6d El-Faham A, Albericio F. Chem. Rev. 2011; 111: 6557
- 6e Valeur E, Bradley M. Chem. Soc. Rev. 2009; 38: 606
- 7 Mukaiyama T, Usui M, Shimada E, Saigo K. Chem. Lett. 1975; 1045
- 8a Matsugi M, Nakamura S, Kunda Y, Sugiyama Y, Shioiri T. Tetrahedron Lett. 2010; 51: 133
- 8b Sugiyama Y, Kurata Y, Kunda Y, Miyazaki A, Matsui J, Nakamura S, Hamamoto H, Shioiri T, Matsugi M. Tetrahedron 2012; 68: 3885
- 9a Sheehan JC, Hess GP. J. Am. Chem. Soc. 1955; 77: 1067
- 9b Neises B, Steglich W. Angew. Chem., Int. Ed. Engl. 1978; 17: 522
- 9c Carpino LA. J. Am. Chem. Soc. 1993; 115: 4397
- 10a Shioiri T, Ninomiya K, Yamada S. J. Am. Chem. Soc. 1972; 94: 6203
- 10b Shioiri T, Yamada S. Chem. Pharm. Bull. 1974; 22: 855
- 10c Shioiri T. TCIMAIL 2007; 134: 2
- 11a Dourtoglou V, Ziegler J.-C, Gross B. Tetrahedron Lett. 1978; 19: 1269
- 11b Knorr R, Trzeciak A, Bannwarth W, Gillessen D. Tetrahedron Lett. 1989; 30: 1927
- 12a Wuts PG. M. Green’s Protective Groups in Organic Synthesis . 5th ed. John Wiley & Sons; Hoboken: 2014: 771
- 12b Banerjee SR, Foss CA, Castanares M, Mease RC, Byun Y, Fox JJ, Lupold SE, Kozikowski AP, Pomper MG. J. Med. Chem. 2008; 51: 4504
- 13 Preparative and analytical f-HPLC were conducted by FluoroFlash® columns (20 mm i.d., 250 mm length and 4.6 mm i.d., 150 mm length) purchased from Fluorous Technologies. The corporation is closing; however, Boron Specialties, LLC can now supply the separation media, see: fluorous.com.
- 14a Curran DP, Dandapani S, Werner S, Matsugi M. Synlett 2004; 1545
- 14b Zhang W, Lu Y, Chen CH, Zeng L, Cassel DB. J. Comb. Chem. 2006; 8: 687
- 14c Fukui Y, Burucner AM, Shin Y, Balachandran R, Day BW, Curran DP. Org. Lett. 2006; 8: 301
- 15a Krishnamurthy VM, Semetey V, Bracher PJ, Shen N, Whitesides GM. J. Am. Chem. Soc. 2007; 129: 1312
- 15b Ghosh AK, Liu C. Org. Lett. 2001; 3: 635
- 16 Miyashita K, Iwaki H, Tai K, Murafuji H, Imanishi T. Chem. Commun. 1998; 1987
- 17 Degel B, Staib P, Rohrer S, Scheiber J, Martina E, Buechold C, Baumann K, Morschhauser J, Schirmeister T. ChemMedChem 2008; 3: 302
- 18 Borissova R, Lammek B, Stjärnkvist P, Sjöholm I. J. Pharm. Sci. 1995; 84: 249
For representative examples, see:
For use of f-HPLC in separation of fluorous compounds, see: