title: Expanding the Genetic Code for a Dinitrophenyl Hapten.
abstract: Haptens, such as dinitrophenyl (DNP) are small molecules that induce strong immune responses when attached to proteins or peptides and, as such, have been exploited for diverse applications. We engineered a Methanosarcina barkeri pyrrolysyl-tRNA synthetase (mbPylRS) to genetically encode a DNP-containing unnatural amino acid, N(6) -(2-(2,4-dinitrophenyl)acetyl)lysine (DnpK). Although this moiety was unstable in Escherichia coli, we found that its stability was enhanced in mammalian HEK 293T cells and was able to induce selective interactions with anti-DNP antibodies. The capability of genetically introducing DNP into proteins is expected to find broad applications in biosensing, immunology, and therapeutics.
authors.affiliation: Department of Chemistry, University of California Riverside, 501 Big Springs Road, Riverside, CA, 92521, USA.
authors.forename: Wei
authors.initials: W
authors.lastname: Ren
authors.affiliation: Department of Chemistry, University of California Riverside, 501 Big Springs Road, Riverside, CA, 92521, USA.
authors.forename: Ao
authors.initials: A
authors.lastname: Ji
authors.affiliation: Department of Chemistry, University of California Riverside, 501 Big Springs Road, Riverside, CA, 92521, USA.|John W. North High School, 1550 3rd Street, Riverside, CA, 92507, USA.
authors.forename: Michael X
authors.initials: MX
authors.lastname: Wang
authors.affiliation: Department of Chemistry, University of California Riverside, 501 Big Springs Road, Riverside, CA, 92521, USA. huiwang.ai@ucr.edu.
authors.forename: Hui-wang
authors.initials: HW
authors.lastname: Ai
mesh_terms: D000604:Amino Acyl-tRNA Synthetases / Q000235:genetics*; D004136:Dinitrobenzenes / Q000737:chemistry* / Q000276:immunology; D005815:Genetic Code; D005818:Genetic Engineering; D057809:HEK293 Cells; D006241:Haptens / Q000737:chemistry* / Q000235:genetics* / Q000276:immunology; D006801:Humans; D008239:Lysine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000235:genetics / Q000276:immunology; D017021:Methanosarcina barkeri / Q000201:enzymology* / Q000235:genetics
chemical_list: D004136:Dinitrobenzenes; D006241:Haptens; C048300:N(2)-acetyl-N(6)-(2,4-dinitrophenyl)lysine; D000604:Amino Acyl-tRNA Synthetases; D008239:Lysine
keywords: dinitrophenyl; genetic code expansion; haptens; unnatural amino acids