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Synlett 2009(20): 3307-3310  
DOI: 10.1055/s-0029-1218369
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Pentafluorophenyl Esters of Nitroveratryloxycarbonyl-Protected Amino Acids

Dong-Sik Shin, Yoon-Sik Lee*
School of Chemical & Biological Engineering, Seoul National University, Kwanak-Ku, Seoul 151-744, Korea
Fax: +82(2)8769625; e-Mail: yslee@snu.ac.kr;
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Publication History

Received 16 September 2009
Publication Date:
18 November 2009 (online)

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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

    References

  • 1a Cahill DJ. J. Immunol. Methods  2001,  250:  81 
    Search in Google Scholar
  • 1b Templin MF. Stoll D. Schrenk M. Traub PC. Vohringer CF. Joos TO. Drug Discov. Today  2002,  7:  815 
    Search in Google Scholar
  • 1c Lam KS. Renil M. Curr. Opin. Chem. Biol.  2002,  6:  353 
    Search in Google Scholar
  • 1d Patek M. Safar P. Smrcina M. Wegrzyniak E. Bjergarde K. Weichsel A. Strop P. J. Comb. Chem.  2004,  6:  43 
    Search in Google Scholar
  • 2a McGall GH. Barone AD. Diggelmann M. Fordor SPA. Gentalen E. Ngo N. J. Am. Chem. Soc.  1997,  119:  5081 
    Search in Google Scholar
  • 2b Pirrung MC. Fallon L. J. Org. Chem.  1998,  63:  241 
    Search in Google Scholar
  • 2c Anderson RC. McGall G. Lipshutz RJ. Top. Curr. Chem.  1998,  194:  117 
    Search in Google Scholar
  • 3a Fodor SPA. Read JL. Pirrung MC. Stryer L. Liu AT. Solas D. Science  1991,  251:  767 
    Search in Google Scholar
  • 3b Holmes CP. Adams CL. Kochersperger LM. Mortensen RB. Aldwin LA. Biopolymers  1995,  37:  199 
    Search in Google Scholar
  • 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 
    Search in Google Scholar
  • 4d Corbett AD. Gleason JL. Tetrahedron Lett.  2002,  43:  1369 
    Search in Google Scholar
  • 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 
    CrossrefSearch in Google Scholar
  • 6 Kisfaludy L. Schön I. Synthesis  1983,  325 
    Thieme Connect
  • 7 Green M. Berman J. Tetrahedron Lett.  1990,  31:  5851 
    CrossrefSearch in Google Scholar
  • 8a Shin DS. Lee KN. Jang KH. Kim JK. Chung WJ. Kim YK. Lee YS. Biosens. Bioelectron.  2003,  19:  485 
    Search in Google Scholar
  • 8b Kim JK. Shin DS. Chung WJ. Jang KH. Lee KN. Kim YK. Lee YS. Colloid Surf. B  2004,  33:  67 
    Search in Google Scholar
  • 9 Bodanszky M. Bodanszky A. The Practice of Peptide Synthesis, Reactivity and Structure Concepts in Organic Chemistry   Vol. 21:  Spinger; Berlin: 1984.  p.12 
    Search in Google Scholar
  • 10a Chung WJ. Lee SM. Choi HM. Lee YS. Cho D. Lim JM. Bull. Korean Chem. Soc.  2006,  27:  37 
    Search in Google Scholar
  • 10b Kim DH. Shin DS. Lee YS. J. Pept. Sci.  2007,  13:  625 
    Search in Google Scholar
  • 11 Kim JM. Baek CW. Park JH. Shin DS. Lee YS. Kim YK. J. Micromech. Microeng.  2002,  12:  688 
    CrossrefSearch in Google Scholar