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Efficient introduction of alkene functionality into proteins in vivo

van Hest, Jan C. M. and Tirrell, David A. (1998) Efficient introduction of alkene functionality into proteins in vivo. FEBS Letters, 428 (1-2). pp. 68-70. ISSN 0014-5793. doi:10.1016/S0014-5793(98)00489-X.

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The methionine analogue 2-amino-5-hexenoic acid (homoallylglycine, Hag) can be utilized by Escherichia coli in the initiation and elongation steps of protein biosynthesis. Use of an E. coli methionine auxotroph and Hag-supplemented medium resulted in replacement of ca. 85% of the methionine residues in mouse dihydrofolate reductase expressed under control of a bacteriophage T5 promoter. N-terminal sequencing indicated 92±5% occupancy of the initiator site by Hag. The vinyl function of Hag remains intact in the purified protein and suggests new chemistries for modification of natural and artificial proteins prepared in bacterial hosts.

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Tirrell, David A.0000-0003-3175-4596
Additional Information:© 1998 Federation of European Biochemical Societies. Received 9 March 1998; revised version received 9 April 1998. The authors thank L.C. Dickinson for assistance with NMR spectroscopy and D.C. Rees for bringing to our attention References [23]and [24]. This work was supported by a grant from the Polymers and Genetics Programs of the US National Science Foundation. The Netherlands Organization for Scientific Research (NWO) and DSM-Research are acknowledged for unrestricted research grants.
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Netherlands Organization for Scientific Research (NWO)UNSPECIFIED
Subject Keywords:Chemical modification; Protein engineering; Amino acid analogue; Homoallylglycine; Methionine replacement
Issue or Number:1-2
Record Number:CaltechAUTHORS:HESfebsl1998
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Official Citation:Jan C.M van Hest, David A Tirrell, Efficient introduction of alkene functionality into proteins in vivo, FEBS Letters, Volume 428, Issues 1–2, 22 May 1998, Pages 68-70, ISSN 0014-5793, (
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:53435
Deposited By: Anne Hormann
Deposited On:06 Feb 2015 03:10
Last Modified:10 Nov 2021 20:02

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