Peptidomimetic bond formation by DNA-templated acyl transfer
Peptidomimetic bond formation by DNA-templated acyl transfer
The efficiencies of DNA-templated acyl transfer reactions between a thioester modified oligonucleotide and a series of amine and thiol based nucleophiles are directly compared. The reactivity of the nucleophile, reaction conditions (solvent, buffer, pH) and linker length all play important roles in determining the efficiency of the transfer reaction. Careful optimisation of the system enables the use of DNA-templated synthesis to form stable peptide-like bonds under mild aqueous conditions close to neutral pH.
1661-1666
McKee, Mireya L.
189d4b60-90b1-4e2f-b95e-2c534bc89087
Evans, Amanda C.
8723c6a2-9a08-4793-acbc-948c398204f9
Gerrard, Simon R.
4ed7b304-42c2-497a-b00d-5ac8a1bedd24
O'Reilly, Rachel K.
086bc91e-2303-4543-b79c-ae16ada0b101
Turberfield, Andrew J.
e12469b0-4ae6-44a5-9099-e9273ab803d4
Stulz, Eugen
9a6c04cf-32ca-442b-9281-bbf3d23c622d
24 November 2011
McKee, Mireya L.
189d4b60-90b1-4e2f-b95e-2c534bc89087
Evans, Amanda C.
8723c6a2-9a08-4793-acbc-948c398204f9
Gerrard, Simon R.
4ed7b304-42c2-497a-b00d-5ac8a1bedd24
O'Reilly, Rachel K.
086bc91e-2303-4543-b79c-ae16ada0b101
Turberfield, Andrew J.
e12469b0-4ae6-44a5-9099-e9273ab803d4
Stulz, Eugen
9a6c04cf-32ca-442b-9281-bbf3d23c622d
McKee, Mireya L., Evans, Amanda C., Gerrard, Simon R., O'Reilly, Rachel K., Turberfield, Andrew J. and Stulz, Eugen
(2011)
Peptidomimetic bond formation by DNA-templated acyl transfer.
Organic & Biomolecular Chemistry, 9 (5), .
(doi:10.1039/C0OB00753F).
(PMID:21270981)
Abstract
The efficiencies of DNA-templated acyl transfer reactions between a thioester modified oligonucleotide and a series of amine and thiol based nucleophiles are directly compared. The reactivity of the nucleophile, reaction conditions (solvent, buffer, pH) and linker length all play important roles in determining the efficiency of the transfer reaction. Careful optimisation of the system enables the use of DNA-templated synthesis to form stable peptide-like bonds under mild aqueous conditions close to neutral pH.
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Published date: 24 November 2011
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Local EPrints ID: 191663
URI: http://eprints.soton.ac.uk/id/eprint/191663
ISSN: 1477-0520
PURE UUID: 1e1862e0-d329-44b1-86e4-f2f2930e22d0
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Date deposited: 23 Jun 2011 13:03
Last modified: 15 Mar 2024 03:26
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Contributors
Author:
Mireya L. McKee
Author:
Amanda C. Evans
Author:
Simon R. Gerrard
Author:
Rachel K. O'Reilly
Author:
Andrew J. Turberfield
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