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Literature DB >> 20074948

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

Ying Huang¹, Wei Wan, William K Russell, Pei-Jing Pai, Zhiyong Wang, David H Russell, Wenshe Liu.

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. Published by Elsevier Ltd.

Entities: Chemical Species

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Year: 2009 PMID： 20074948 DOI： 10.1016/j.bmcl.2009.12.077

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

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Cited

22 in total

Review 1. Designer proteins: applications of genetic code expansion in cell biology.

Authors: Lloyd Davis; Jason W Chin
Journal: Nat Rev Mol Cell Biol Date: 2012-02-15 Impact factor: 94.444

2. A genetically encoded aldehyde for rapid protein labelling.

Authors: Alfred Tuley; Yan-Jiun Lee; Bo Wu; Zhiyong U Wang; Wenshe R Liu
Journal: Chem Commun (Camb) Date: 2014-07-18 Impact factor: 6.222

Review 3. Oximes and Hydrazones in Bioconjugation: Mechanism and Catalysis.

Authors: Dominik K Kölmel; Eric T Kool
Journal: Chem Rev Date: 2017-06-22 Impact factor: 60.622

4. Proteins with Site-Specific Lysine Methylation.

Authors: Zhipeng A Wang; Wenshe R Liu
Journal: Chemistry Date: 2017-08-01 Impact factor: 5.236

Review 5. Pyrrolysyl-tRNA synthetase: an ordinary enzyme but an outstanding genetic code expansion tool.

Authors: Wei Wan; Jeffery M Tharp; Wenshe R Liu
Journal: Biochim Biophys Acta Date: 2014-03-12

6. Catalyst-free and site-specific one-pot dual-labeling of a protein directed by two genetically incorporated noncanonical amino acids.

Authors: Bo Wu; Zhiyong Wang; Ying Huang; Wenshe R Liu
Journal: Chembiochem Date: 2012-05-24 Impact factor: 3.164

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

Review 1. Designer proteins: applications of genetic code expansion in cell biology.

2. A genetically encoded aldehyde for rapid protein labelling.

Review 3. Oximes and Hydrazones in Bioconjugation: Mechanism and Catalysis.

4. Proteins with Site-Specific Lysine Methylation.

Review 5. Pyrrolysyl-tRNA synthetase: an ordinary enzyme but an outstanding genetic code expansion tool.

6. Catalyst-free and site-specific one-pot dual-labeling of a protein directed by two genetically incorporated noncanonical amino acids.

7. A Pictet-Spengler ligation for protein chemical modification.

8. Towards reassigning the rare AGG codon in Escherichia coli.

9. Multiple site-selective insertions of noncanonical amino acids into sequence-repetitive polypeptides.

10. A genetically encoded acrylamide functionality.