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        Synthesis  2004(18): 3011-3016  
DOI: 10.1055/s-2004-834875
   DOI: 10.1055/s-2004-834875
PAPER
© Georg Thieme Verlag Stuttgart · New YorkSynthesis of N α-Fmoc N,N′-bis-Boc-5-, 6- and 8-guanyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid (5-GTIC, 6-GTIC and 8-GTIC)
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                              Received
                              13 July 2004 
                      
Publikationsdatum:
21. Oktober 2004 (online)
            
         
      
   Publikationsverlauf
Publikationsdatum:
21. Oktober 2004 (online)

Abstract
N α-Fmoc N,N′-bis-Boc-5-, 6- and 8-guanyl-Tic-OH (5-, 6- and 8-GTIC), three conformationally constrained amino acids with basic properties, have been synthesized by microwave irradiation. These amino acids combine the basic features of arginine with the aromatic features of phenylalanine and can be utilized as functional tools in peptide-based structure-activity studies.
Key words
unconventional amino acid - microwave - synthesis - GTIC
- 1a 
             
            Hruby VJ. Biopolymers 1993, 31: 1073
- 1b 
             
            Hruby VJ.Li G.Haskell-Luevano C.Shenderovich M. Biopolymers 1997, 43: 219
- 1c 
             
            Toniolo C. Int. J. Pept. Protein Res. 1990, 35: 287
- 1d 
             
            Giannis A.Kolter T. Angew. Chem., Int. Ed. Engl. 1993, 32: 1244
- 1e 
             
            Fiori S.Pegoraro S.Rudolph-Bohner S.Cramer J.Moroder L. Biopolymers 2000, 53: 550
- 2a 
             
            Schiller PW.Weltrowska TM.Nguyen D.Lemieux C.Chung NN.Marsden BJ.Wilkes BC. J. Med. Chem. 1991, 34: 3125
- 2b 
             
            Temussi PA.Salvadori S.Amodeo P.Bianchi C.Guerrini R.Tomatis R.Lazarus LH.Picone D.Tancredi T. Biochem. Biophys. Res. Commun. 1994, 198: 933
- 2c 
             
            Salvadori S.Attila M.Balboni G.Bianchi C.Bryant SD.Crescenzi O.Guerrini R.Picone D.Tancredi T.Temussi PA.Lazarus LH. Mol. Med. 1995, 1: 678
- 2d 
             
            Tancredi T.Salvadori S.Amodeo P.Picone D.Lazarus LH.Bryant SD.Guerrini R.Marzola G.Temussi PA. Eur. J. Biochem. 1994, 224: 241
- 3 
             
            Caliendo G.Calignano A.Grieco P.Mancuso F.Perissutti E.Santini A.Santagada V. Biopolymers 1995, 36: 409
- 4 
             
            Caliendo G.Fiorino F.Greco P.Perissutti E.De Luca S.Giuliano A.Santelli G.Severino B.Santagada V. Il Farmaco 1999, 54: 785
- 5 
             
            Guba W.Haessner R.Breiphol G.Henke S.Knolle J.Santagada V.Kessler H. J. Am. Chem. Soc. 1994, 116: 7532
- 6 
             
            Pimenta DC.Melo LR.Caliendo G.Santagada V.Fiorino F.Severino B.De Nucci G.Juliano L.Juliano M. Biol. Chem. 2002, 383 (5): 853
- 7a 
             
            Kazmierski WM.Urbanczyk-Likowska Z.Hruby V. J. Org. Chem. 1994, 59: 1789
- 7b 
             
            Skiles JW.Suh JT.Williams BE.Menard PR.Barton JN.Loev B.Hones H.Neiss ES.Schwah A.Mann WS.Khandwala A.Wolf PS.Weinryb I. J. Med. Chem. 1986, 26: 784
- 7c 
             
            Schöllkopf U.Hinrichs R.Lonsky R. Angew. Chem., Int. Ed. Engl. 1987, 26: 143
- 7d 
             
            Chen HG.Goel OP. Synth. Commun. 1995, 25: 49
- 7e 
             
            Wang C.Mosberg HI. Tetrahedron Lett. 1995, 36: 3623
- 8 
             
            Santagada V.Fiorino F.Severino B.Salvadori S.Lazarus LH.Bryant SD.Caliendo G. Tetrahedron Lett. 2001, 42: 3507
- 9a 
             
            Santagada V.Perissutti E.Fiorino F.Vivenzio B.Caliendo G. Tetrahedron Lett. 2001, 42: 2397
- 9b 
             
            Santagada V.Fiorino F.Perissutti E.Severino B.De Filippis V.Vivenzio B.Caliendo G. Tetrahedron Lett. 2001, 42: 5171
- 9c 
             
            Caliendo G.Fiorino F.Perissutti E.Severino B.Gessi S.Cattabriga E.Borea PA.Santagada V. Eur. J. Med. Chem. 2001, 36 (11-12): 873
- 9d 
             
            Santagada V.Perissutti E.Caliendo G. Curr. Med. Chem. 2002, 9 (13): 1251
- 9e 
             
            Loupy A.Petit A.Hamelin J.Texier-Boullet F.Jacquault P.Mathe D. Synthesis 1998, 1213
- 9f 
             
            Galema SA. Chem. Soc. Rev. 1997, 26: 233
- 9g 
             
            Caddick S. Tetrahedron 1995, 51: 10403
- 9h 
             
            Larhed M.Hallberg A. Drug Discovery Today 2001, 6: 406
- 10 
             
            Grunewald GL.Dahanukar VH.Teoh B.Criscione KR. J. Med. Chem. 1999, 42: 1982
 
    