Genetic incorporation of an aliphatic keto-containing amino acid into proteins for their site-specific modifications

Ying Huang; Wei Wan; William K. Russell; Pei Jing Pai; Zhiyong Wang; David H. Russell; Wenshe Liu

doi:10.1016/j.bmcl.2009.12.077

Genetic incorporation of an aliphatic keto-containing amino acid into proteins for their site-specific modifications

Ying Huang, Wei Wan, William K. Russell, Pei Jing Pai, Zhiyong Wang, David H. Russell, Wenshe Liu

Research output: Contribution to journal › Article › peer-review

46 Scopus citations

Abstract

2-Amino-8-oxononanoic acid has been genetically incorporated into proteins in Escherichia coli by the use of an evolved pyrrolysyl-tRNA synthetase/pylT pair. The direct usage of the exclusive reactivity of the keto group in this amino acid with hydrazide- and alkoxyamine-bearing compounds to site-specifically label proteins under a mild condition close to physiological pH exhibited a very high efficiency.

Original language	English (US)
Pages (from-to)	878-880
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	3
DOIs	https://doi.org/10.1016/j.bmcl.2009.12.077
State	Published - Feb 1 2010
Externally published	Yes

Keywords

2-Amino-8-oxononanoic acid
Amber suppression
Genetic code expansion
Keto
Ne-acetyl-lysine

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2009.12.077

Cite this

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title = "Genetic incorporation of an aliphatic keto-containing amino acid into proteins for their site-specific modifications",

abstract = "2-Amino-8-oxononanoic acid has been genetically incorporated into proteins in Escherichia coli by the use of an evolved pyrrolysyl-tRNA synthetase/pylT pair. The direct usage of the exclusive reactivity of the keto group in this amino acid with hydrazide- and alkoxyamine-bearing compounds to site-specifically label proteins under a mild condition close to physiological pH exhibited a very high efficiency.",

keywords = "2-Amino-8-oxononanoic acid, Amber suppression, Genetic code expansion, Keto, Ne-acetyl-lysine",

author = "Ying Huang and Wei Wan and Russell, {William K.} and Pai, {Pei Jing} and Zhiyong Wang and Russell, {David H.} and Wenshe Liu",

note = "Funding Information: This work was supported by Welch Grant A-1715 and Texas A&M Chemistry Department . We thank Prof. Jiong Yang and his group for their help in the KetoK synthesis. ",

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doi = "10.1016/j.bmcl.2009.12.077",

language = "English (US)",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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T1 - Genetic incorporation of an aliphatic keto-containing amino acid into proteins for their site-specific modifications

AU - Huang, Ying

AU - Wan, Wei

AU - Russell, William K.

AU - Pai, Pei Jing

AU - Wang, Zhiyong

AU - Russell, David H.

AU - Liu, Wenshe

N1 - Funding Information: This work was supported by Welch Grant A-1715 and Texas A&M Chemistry Department . We thank Prof. Jiong Yang and his group for their help in the KetoK synthesis.

PY - 2010/2/1

Y1 - 2010/2/1

N2 - 2-Amino-8-oxononanoic acid has been genetically incorporated into proteins in Escherichia coli by the use of an evolved pyrrolysyl-tRNA synthetase/pylT pair. The direct usage of the exclusive reactivity of the keto group in this amino acid with hydrazide- and alkoxyamine-bearing compounds to site-specifically label proteins under a mild condition close to physiological pH exhibited a very high efficiency.

AB - 2-Amino-8-oxononanoic acid has been genetically incorporated into proteins in Escherichia coli by the use of an evolved pyrrolysyl-tRNA synthetase/pylT pair. The direct usage of the exclusive reactivity of the keto group in this amino acid with hydrazide- and alkoxyamine-bearing compounds to site-specifically label proteins under a mild condition close to physiological pH exhibited a very high efficiency.

KW - 2-Amino-8-oxononanoic acid

KW - Amber suppression

KW - Genetic code expansion

KW - Keto

KW - Ne-acetyl-lysine

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DO - 10.1016/j.bmcl.2009.12.077

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 3

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Genetic incorporation of an aliphatic keto-containing amino acid into proteins for their site-specific modifications

Abstract

Keywords

ASJC Scopus subject areas

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