Synthesis 2005(6): 888-892  
DOI: 10.1055/s-2005-861854
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of a Cyclen-Functionalized α-Amino Acid and its Incorporation into Peptide Sequence

Shan-Yong Chena, Yu Huanga, Guo-Lin Zhangb, Hua Chenga, Chuan-Qin Xiaa, Li-Jian Maa, Hong Yua, Xiao-Qi Yu*a
a Department of Chemistry, Key Laboratory of Green Chemistry and Technology (Ministry of Education), Sichuan University, Chengdu 610064, P. R. China
b Chengdu Institute of Biology, The Chinese Academy of Sciences, Chengdu 610041, P. R. China
Fax: +86(28)85415886; e-Mail: [email protected];
Further Information

Publication History

Received 27 September 2004
Publication Date:
10 March 2005 (online)

Abstract

A cyclen-functionlized α-amino acid was obtained through embedding cyclen into the side chain of homoserine. The α-amino acid can be conveniently incorporated into peptide sequence to form new ligands, which have strong coordination ability for transition metal ions.

    References

  • 1 Dondoni A. Massi A. Minghini E. Bertolasi V. Tetrahedron  2004,  60:  2311 
  • 2 Handel TM. Williams SA. DeGrado WF. Science  1993,  261:  879 
  • 3 Muheim A. Todd RJ. Casimiro DR. Gray HB. Amold FH. J. Am. Chem. Soc.  1993,  115:  5312 
  • 4 Ghadiri MR. Soares C. Choi C. J. Am. Chem. Soc.  1992,  114:  4000 
  • 5 Ruan F. Chen Y. Hopkins PB. J. Am. Chem. Soc.  1990,  112:  9403 
  • 6 Mecklenburg SL. Peek BM. Schoonover JR. McCafferty DG. Wall CG. Erickson BW. Meyer TJ. J. Am. Chem. Soc.  1993,  115:  5479 
  • 7 Alexander V. Chem. Rev.  1995,  95:  273 
  • 8 Caravan P. Ellison JJ. McMurry TJ. Lauffer RB. Chem. Rev.  1999,  99:  2293 
  • 9 Bianchi A. Calabi L. Corana F. Fontana S. Losi P. Maiocchi A. Paleari L. Valtancoli B. Coord. Chem. Rev.  2000,  204:  309 
  • 10 Reany O. Gunnlaugsson T. Parker D. Chem. Commun.  2000,  473 
  • 11 Lim NC. Yao LL. Freake H. Bruckner C. Bioorg. Med. Chem. Lett.  2003,  13:  2251 
  • 12 Shionoya M. Kimura E. Shiro M. J. Am. Chem. Soc.  1993,  115:  6730 
  • 13 Shionoya M. Ikeda T. Kimura E. Shiro M. J. Am. Chem. Soc.  1994,  116:  3848 
  • 14 Epstein DM. Chappell LL. Khalili H. Supkowski RM. Horrocks WD. Morrow JR. Inorg. Chem.  2000,  39:  2130 
  • 15 Kimura E. Shionoya M. Hoshino A. Ikeda T. Yamada Y. J. Am. Chem. Soc.  1992,  114:  10134 
  • 16 Zhang X. van Eldik R. Inorg. Chem.  1995,  34:  5606 
  • 17 Brechbiel MW. Pippin CG. McMurry TJ. Milenic D. Roselli M. Colcher D. Gansow OA. J. Chem. Soc., Chem. Commun.  1991,  1169 
  • 18 Kumar K. Magerstadt M. Gansow OA. J. Chem. Soc., Chem. Commun.  1989,  145 
  • 19a Jeon JW. Son SJ. Yoo CE. Hong IS. Suh J. Bioorg. Med. Chem.  2003,  11:  2901 
  • 19b Yoo CE. Chae PS. Kim JE. Jeong EJ. Suh J. J. Am. Chem. Soc.  2003,  125:  14580 
  • 19c Jeon JW. Son SJ. Yoo CE. Hong IS. Song JB. Suh J. Org. Lett.  2002,  4:  4155 
  • 20 Miltschizky S. Konig B. Synth. Commun.  2004,  34:  2077 
  • 21 Burger MT. Still WC. J. Org. Chem.  1995,  60:  7382 
  • 22 Atkins TJ. Richman JE. Oettle WF. Org. Synth.  1978,  58:  86 
  • 23 Boyle PH. Davis AP. Dempsey KJ. Hosken GD. Tetrahedron: Asymmetry  1995,  6:  2819 
  • 24 Anelli PL. Murru M. Uggeri F. Virtuani M. J. Chem. Soc., Chem. Commun.  1991,  1317 
  • 25 Baker WC. Choi MJ. Hill DC. Petillo PA. J. Org. Chem.  1999,  64:  2683 
  • 26 Li C. Wong W.-T. Tetrahedron Lett.  2002,  43:  3217 
  • 27 Barton DHR. Crich D. Herve Y. Potier P. Tetrahedron  1985,  41:  4347