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Incorporation of unsaturated isoleucine analogues into proteins in vivo

Michon, Thierry and Barbot, Francis and Tirrell, David (2002) Incorporation of unsaturated isoleucine analogues into proteins in vivo. In: Plant Biopolymer Science : Food and Non-Food Applications. Special Publication. No.276. Royal Society of Chemistry , Cambridge, UK, pp. 63-72. ISBN 978-0-85404-856-4.

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The translational activity of various unsaturated analogs of L-isoleucine was evaluated using an Escherichia coli strain auxotrophic for isoleucine. It was observed that the alkene [2-amino-3-methyl-4-pentenoic acid (2)] and alkyne [2-amino-3-rnethyl-4-pentynoic acid (3)] derivatives of L-isoleucine can support protein synthesis at levels approximately 50% of that observed in cultures supplemented with isoleucine. However, no incorporation of the αC or βC methylated derivatives could be detected. In order to examine the stereoselectivity of incorporation, the (2S, 3s) and (2S, 3R) diastereomers of 2 and 3 were prepared. The extents of isoleucine substitution in vivo were 80% and 70% for (2S, 3S)-2 and (2S, 3S)-3, respectively, under the conditions examined in this study.

Item Type:Book Section
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Tirrell, David0000-0003-3175-4596
Additional Information:© 2002 Royal Society of Chemistry. The authors thank NATO for its financial support to T. M.'s year-long sabbatical. We are grateful to Kristi Kiick for fruitful discussions.
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North Atlantic Treaty Organization (NATO)UNSPECIFIED
Series Name:Special Publication
Issue or Number:276
Record Number:CaltechAUTHORS:20160801-122125209
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:69354
Deposited By: George Porter
Deposited On:01 Aug 2016 19:40
Last Modified:11 Nov 2021 04:12

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