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Synlett 2009(20): 3307-3310
DOI: 10.1055/s-0029-1218369
DOI: 10.1055/s-0029-1218369
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Pentafluorophenyl Esters of Nitroveratryloxycarbonyl-Protected Amino Acids
Further Information
Received
16 September 2009
Publication Date:
18 November 2009 (online)
Publication History
Publication Date:
18 November 2009 (online)
Abstract
For efficient peptide synthesis on a glass chip, 20 kinds of pentafluorophenyl (Pfp) esters of nitroveratryloxycarbonyl (NVOC)-protected amino acids were synthesized by using Pfp trifluoroacetate. Simple purification step gave moderate to high yield. The first loading time of each amino acid on glass surface was 30-60 min. The UV cleavage of the NVOC group was completed within 10 minutes.
Key words
NVOC amino acid - Pfp ester - in situ synthesis - peptide microarray
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1a
Cahill DJ. J. Immunol. Methods 2001, 250: 81 -
1b
Templin MF.Stoll D.Schrenk M.Traub PC.Vohringer CF.Joos TO. Drug Discov. Today 2002, 7: 815 -
1c
Lam KS.Renil M. Curr. Opin. Chem. Biol. 2002, 6: 353 -
1d
Patek M.Safar P.Smrcina M.Wegrzyniak E.Bjergarde K.Weichsel A.Strop P. J. Comb. Chem. 2004, 6: 43 -
2a
McGall GH.Barone AD.Diggelmann M.Fordor SPA.Gentalen E.Ngo N. J. Am. Chem. Soc. 1997, 119: 5081 -
2b
Pirrung MC.Fallon L. J. Org. Chem. 1998, 63: 241 -
2c
Anderson RC.McGall G.Lipshutz RJ. Top. Curr. Chem. 1998, 194: 117 -
3a
Fodor SPA.Read JL.Pirrung MC.Stryer L.Liu AT.Solas D. Science 1991, 251: 767 -
3b
Holmes CP.Adams CL.Kochersperger LM.Mortensen RB.Aldwin LA. Biopolymers 1995, 37: 199 -
4a
Schön I.Kisfaludy L. Synthesis 1986, 303 -
4b
Gyi JI.Kinsman RG.Rees AR. Synlett 1995, 205 -
4c
Verheijen JC.Grotenbreg GM.de Ruyter LH.van der Klein PAM.van der Marel GA.van Boom JH. Tetrahedron Lett. 2000, 41: 3991 -
4d
Corbett AD.Gleason JL. Tetrahedron Lett. 2002, 43: 1369 -
4e
Olsen CA.Witt M.Jaroszewski JW.Franzyk H. Synlett 2004, 473 - 5
Thomson SA.Josey JA.Cadilla R.Gaul MD.Hassman CF.Luzzio MJ.Pipe AJ.Reed KL.Ricca DJ.Wiethe RW.Noble SA. Tetrahedron 1995, 51: 6179 - 6
Kisfaludy L.Schön I. Synthesis 1983, 325 - 7
Green M.Berman J. Tetrahedron Lett. 1990, 31: 5851 -
8a
Shin DS.Lee KN.Jang KH.Kim JK.Chung WJ.Kim YK.Lee YS. Biosens. Bioelectron. 2003, 19: 485 -
8b
Kim JK.Shin DS.Chung WJ.Jang KH.Lee KN.Kim YK.Lee YS. Colloid Surf. B 2004, 33: 67 - 9
Bodanszky M.Bodanszky A. The Practice of Peptide Synthesis, Reactivity and Structure Concepts in Organic Chemistry Vol. 21: Spinger; Berlin: 1984. p.12 -
10a
Chung WJ.Lee SM.Choi HM.Lee YS.Cho D.Lim JM. Bull. Korean Chem. Soc. 2006, 27: 37 -
10b
Kim DH.Shin DS.Lee YS. J. Pept. Sci. 2007, 13: 625 - 11
Kim JM.Baek CW.Park JH.Shin DS.Lee YS.Kim YK. J. Micromech. Microeng. 2002, 12: 688