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Protein Engineering vol. 16 no. 9 pp. 699-706, 2003
© 2003 Oxford University Press

Synthesis of a novel histidine analogue and its efficient incorporation into a protein in vivo

Yutaka Ikeda1,2, Shun-ichi Kawahara2, Masumi Taki2, Atsushi Kuno2,3, Tsunemi Hasegawa3 and Kazunari Taira1,2,4

1Department of Chemistry and Biotechnology, School of Engineering, University of Tokyo, 7-3-1 Hongo, Tokyo 113-8656, 2Gene Function Research Center, National Institute of Advanced Industrial Science and Technology (AIST), Tukuba Science City 305-8562 and 3Department of Material and Biological Chemistry, Faculty of Science, Yamagata University, Yamagata 990-8560, Japan

4 To whom correspondence should be addressed, at the Tokyo address. e-mail: taira{at}chembio.t.u-tokyo.ac.jp

Proteins containing unnatural amino acids have immense potential in biotechnology and medicine. We prepared several histidine analogues including a novel histidine analogue, ß-(1,2,3-triazol-4-yl)-DL-alanine. These histidine analogues were assayed for translational activity in histidine-auxotrophic Escherichia coli strain UTH780. We observed that several histidine analogues, including our novel histidine analogue, were efficiently incorporated into the protein in vivo; however, other analogues were rejected. These results suggest that the hydrogen atom at a specific position seriously affects incorporation.

Received April 10, 2003; revised June 20, 2003; accepted July 22, 2003.


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