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

Shan-Yong Chen; Yu Huang; Guo-Lin Zhang; Hua Cheng; Chuan-Qin Xia; Li-Jian Ma; Hong Yu; Xiao-Qi Yu

doi:10.1055/s-2005-861854

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

Shan-Yong Chen^a, Yu Huang^a, Guo-Lin Zhang^b, Hua Cheng^a, Chuan-Qin Xia^a, Li-Jian Ma^a, Hong Yu^a, 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: schemorg@mail.sc.cninfo.net;

Abstract

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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.

Key words

cyclen - unnatural amino acid - metallopeptides

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References

<A NAME="RF13904SS-1">1</A> Dondoni A. Massi A. Minghini E. Bertolasi V. Tetrahedron 2004, 60: 2311

<A NAME="RF13904SS-2">2</A> Handel TM. Williams SA. DeGrado WF. Science 1993, 261: 879

<A NAME="RF13904SS-3">3</A> Muheim A. Todd RJ. Casimiro DR. Gray HB. Amold FH. J. Am. Chem. Soc. 1993, 115: 5312

<A NAME="RF13904SS-4">4</A> Ghadiri MR. Soares C. Choi C. J. Am. Chem. Soc. 1992, 114: 4000

<A NAME="RF13904SS-5">5</A> Ruan F. Chen Y. Hopkins PB. J. Am. Chem. Soc. 1990, 112: 9403

<A NAME="RF13904SS-6">6</A> Mecklenburg SL. Peek BM. Schoonover JR. McCafferty DG. Wall CG. Erickson BW. Meyer TJ. J. Am. Chem. Soc. 1993, 115: 5479

<A NAME="RF13904SS-7">7</A> Alexander V. Chem. Rev. 1995, 95: 273

<A NAME="RF13904SS-8">8</A> Caravan P. Ellison JJ. McMurry TJ. Lauffer RB. Chem. Rev. 1999, 99: 2293

<A NAME="RF13904SS-9">9</A> Bianchi A. Calabi L. Corana F. Fontana S. Losi P. Maiocchi A. Paleari L. Valtancoli B. Coord. Chem. Rev. 2000, 204: 309

<A NAME="RF13904SS-10">10</A> Reany O. Gunnlaugsson T. Parker D. Chem. Commun. 2000, 473

<A NAME="RF13904SS-11">11</A> Lim NC. Yao LL. Freake H. Bruckner C. Bioorg. Med. Chem. Lett. 2003, 13: 2251

<A NAME="RF13904SS-12">12</A> Shionoya M. Kimura E. Shiro M. J. Am. Chem. Soc. 1993, 115: 6730

<A NAME="RF13904SS-13">13</A> Shionoya M. Ikeda T. Kimura E. Shiro M. J. Am. Chem. Soc. 1994, 116: 3848

<A NAME="RF13904SS-14">14</A> Epstein DM. Chappell LL. Khalili H. Supkowski RM. Horrocks WD. Morrow JR. Inorg. Chem. 2000, 39: 2130

<A NAME="RF13904SS-15">15</A> Kimura E. Shionoya M. Hoshino A. Ikeda T. Yamada Y. J. Am. Chem. Soc. 1992, 114: 10134

<A NAME="RF13904SS-16">16</A> Zhang X. van Eldik R. Inorg. Chem. 1995, 34: 5606

<A NAME="RF13904SS-17">17</A> Brechbiel MW. Pippin CG. McMurry TJ. Milenic D. Roselli M. Colcher D. Gansow OA. J. Chem. Soc., Chem. Commun. 1991, 1169

<A NAME="RF13904SS-18">18</A> Kumar K. Magerstadt M. Gansow OA. J. Chem. Soc., Chem. Commun. 1989, 145

<A NAME="RF13904SS-19A">19a</A> Jeon JW. Son SJ. Yoo CE. Hong IS. Suh J. Bioorg. Med. Chem. 2003, 11: 2901

<A NAME="RF13904SS-19B">19b</A> Yoo CE. Chae PS. Kim JE. Jeong EJ. Suh J. J. Am. Chem. Soc. 2003, 125: 14580

<A NAME="RF13904SS-19C">19c</A> Jeon JW. Son SJ. Yoo CE. Hong IS. Song JB. Suh J. Org. Lett. 2002, 4: 4155

<A NAME="RF13904SS-20">20</A> Miltschizky S. Konig B. Synth. Commun. 2004, 34: 2077

<A NAME="RF13904SS-21">21</A> Burger MT. Still WC. J. Org. Chem. 1995, 60: 7382

<A NAME="RF13904SS-22">22</A> Atkins TJ. Richman JE. Oettle WF. Org. Synth. 1978, 58: 86

<A NAME="RF13904SS-23">23</A> Boyle PH. Davis AP. Dempsey KJ. Hosken GD. Tetrahedron: Asymmetry 1995, 6: 2819

<A NAME="RF13904SS-24">24</A> Anelli PL. Murru M. Uggeri F. Virtuani M. J. Chem. Soc., Chem. Commun. 1991, 1317

<A NAME="RF13904SS-25">25</A> Baker WC. Choi MJ. Hill DC. Petillo PA. J. Org. Chem. 1999, 64: 2683

<A NAME="RF13904SS-26">26</A> Li C. Wong W.-T. Tetrahedron Lett. 2002, 43: 3217

<A NAME="RF13904SS-27">27</A> Barton DHR. Crich D. Herve Y. Potier P. Tetrahedron 1985, 41: 4347