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- Publisher Website: 10.1016/j.tet.2012.04.032
- Scopus: eid_2-s2.0-84861684664
- WOS: WOS:000305381700005
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Article: DNA-directed formation of peptide bond: A model study toward DNA-programmed peptide ligation
Title | DNA-directed formation of peptide bond: A model study toward DNA-programmed peptide ligation |
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Authors | |
Keywords | Acyl transfer reaction DNA-templated synthesis Native chemical ligation Peptide bond formation Thiol-thioester exchange |
Issue Date | 2012 |
Publisher | Pergamon. The Journal's web site is located at http://www.elsevier.com/locate/tet |
Citation | Tetrahedron, 2012, v. 68 n. 26, p. 5152-5156 How to Cite? |
Abstract | A model study of DNA-directed peptide ligation has been developed by transferring fluorescent reporting group from small molecule thioester to a DNA strand (template DNA) in the presence of a thiol-functionalized DNA strand (auxiliary DNA), mimicking the Native Chemical Ligation (NCL) reaction. This DNA-directed transfer shows dependence on the sequence complementarity of the two DNA strands, with in situ generated 4-thiolphenylmethyl functionalized oligonucleotide as the auxiliary DNA strand, under mild basic condition (pH=8.5), and with tris(2-carboxyethyl) phosphine hydrochloride (TCEP) as a reducing agent. Reactions with different amino acid α-thioesters resulted in varied transfer efficiencies from glycine to α-substituted amino acids. This study has provided the basic foundation to use DNA-programmed chemistry toward the chemical synthesis or unnatural modification of protein molecules. © 2012 Published by Elsevier Ltd. |
Persistent Identifier | http://hdl.handle.net/10722/221122 |
ISSN | 2023 Impact Factor: 2.1 2023 SCImago Journal Rankings: 0.406 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Zhang, C | - |
dc.contributor.author | Li, Y | - |
dc.contributor.author | Zhang, M | - |
dc.contributor.author | Li, X | - |
dc.date.accessioned | 2015-10-27T09:34:04Z | - |
dc.date.available | 2015-10-27T09:34:04Z | - |
dc.date.issued | 2012 | - |
dc.identifier.citation | Tetrahedron, 2012, v. 68 n. 26, p. 5152-5156 | - |
dc.identifier.issn | 0040-4020 | - |
dc.identifier.uri | http://hdl.handle.net/10722/221122 | - |
dc.description.abstract | A model study of DNA-directed peptide ligation has been developed by transferring fluorescent reporting group from small molecule thioester to a DNA strand (template DNA) in the presence of a thiol-functionalized DNA strand (auxiliary DNA), mimicking the Native Chemical Ligation (NCL) reaction. This DNA-directed transfer shows dependence on the sequence complementarity of the two DNA strands, with in situ generated 4-thiolphenylmethyl functionalized oligonucleotide as the auxiliary DNA strand, under mild basic condition (pH=8.5), and with tris(2-carboxyethyl) phosphine hydrochloride (TCEP) as a reducing agent. Reactions with different amino acid α-thioesters resulted in varied transfer efficiencies from glycine to α-substituted amino acids. This study has provided the basic foundation to use DNA-programmed chemistry toward the chemical synthesis or unnatural modification of protein molecules. © 2012 Published by Elsevier Ltd. | - |
dc.language | eng | - |
dc.publisher | Pergamon. The Journal's web site is located at http://www.elsevier.com/locate/tet | - |
dc.relation.ispartof | Tetrahedron | - |
dc.rights | © <year>. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/ | - |
dc.subject | Acyl transfer reaction | - |
dc.subject | DNA-templated synthesis | - |
dc.subject | Native chemical ligation | - |
dc.subject | Peptide bond formation | - |
dc.subject | Thiol-thioester exchange | - |
dc.title | DNA-directed formation of peptide bond: A model study toward DNA-programmed peptide ligation | - |
dc.type | Article | - |
dc.identifier.email | Li, X: xiaoyuli@hku.hk | - |
dc.identifier.authority | Li, X=rp02080 | - |
dc.identifier.doi | 10.1016/j.tet.2012.04.032 | - |
dc.identifier.scopus | eid_2-s2.0-84861684664 | - |
dc.identifier.hkuros | 284530 | - |
dc.identifier.volume | 68 | - |
dc.identifier.issue | 26 | - |
dc.identifier.spage | 5152 | - |
dc.identifier.epage | 5156 | - |
dc.identifier.isi | WOS:000305381700005 | - |
dc.publisher.place | United Kingdom | - |
dc.identifier.issnl | 0040-4020 | - |