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2?-Substituted 2-amino-3-methylpyridine ribonucleosides in triplex-forming oligonucleotides: triplex stability is determined by chemical environment

2?-Substituted 2-amino-3-methylpyridine ribonucleosides in triplex-forming oligonucleotides: triplex stability is determined by chemical environment
2?-Substituted 2-amino-3-methylpyridine ribonucleosides in triplex-forming oligonucleotides: triplex stability is determined by chemical environment
A new synthetic route to the phosphoramidite monomer of 2-amino-3-methyl-5-(2?-O-methyl-?-D-ribofuranosyl)pyridine (Me-MAP) and its 2?-O-methoxyethyl analogue (MOE-MAP) has been established using D-ribose and 2-amino-3-methyl-5-bromopyridine as precursors. Ultraviolet melting and DNase I footprinting studies indicate that the triplex stabilizing properties of 2?-modified MAPs are determined by the conformation of the entire oligonucleotide backbone. Me-MAP confers a higher triplex stability than 2?-deoxycytidine whereas triplex stabilization by MOE-MAP is similar to that of dC. Incorporation of Me-MAP or MOE-MAP into oligonucleotides renders them dramatically more resistant to degradation by serum nucleases than incorporation of 2-amino-3-methyl-5-(2?-deoxy-?-D-ribofuranosyl)pyridine (dMAP) or dC.



2040-2503
550-558
Lou, Chenguang
bf8d79e9-a81a-4483-ab89-13244aac3eb6
Xiao, Qiang
abe7be8e-6131-403e-aa22-2fa5518fdc54
Tailor, Radha R.
686d0612-389a-4403-aa16-08922120ce84
Ben Gaied, Nouha
e97c4e6d-2eaf-4c2b-8b42-f82ac35671ff
Gale, Nittaya
eead6253-2431-407b-ab6b-92e35d41c3ef
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c
Fox, Keith R.
9da5debc-4e45-473e-ab8c-550d1104659f
Brown, Tom
a64aae36-bb30-42df-88a2-11be394e8c89
Lou, Chenguang
bf8d79e9-a81a-4483-ab89-13244aac3eb6
Xiao, Qiang
abe7be8e-6131-403e-aa22-2fa5518fdc54
Tailor, Radha R.
686d0612-389a-4403-aa16-08922120ce84
Ben Gaied, Nouha
e97c4e6d-2eaf-4c2b-8b42-f82ac35671ff
Gale, Nittaya
eead6253-2431-407b-ab6b-92e35d41c3ef
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c
Fox, Keith R.
9da5debc-4e45-473e-ab8c-550d1104659f
Brown, Tom
a64aae36-bb30-42df-88a2-11be394e8c89

Lou, Chenguang, Xiao, Qiang, Tailor, Radha R., Ben Gaied, Nouha, Gale, Nittaya, Light, Mark E., Fox, Keith R. and Brown, Tom (2011) 2?-Substituted 2-amino-3-methylpyridine ribonucleosides in triplex-forming oligonucleotides: triplex stability is determined by chemical environment. MedChemComm, 2 (6), 550-558. (doi:10.1039/c1md00068c).

Record type: Article

Abstract

A new synthetic route to the phosphoramidite monomer of 2-amino-3-methyl-5-(2?-O-methyl-?-D-ribofuranosyl)pyridine (Me-MAP) and its 2?-O-methoxyethyl analogue (MOE-MAP) has been established using D-ribose and 2-amino-3-methyl-5-bromopyridine as precursors. Ultraviolet melting and DNase I footprinting studies indicate that the triplex stabilizing properties of 2?-modified MAPs are determined by the conformation of the entire oligonucleotide backbone. Me-MAP confers a higher triplex stability than 2?-deoxycytidine whereas triplex stabilization by MOE-MAP is similar to that of dC. Incorporation of Me-MAP or MOE-MAP into oligonucleotides renders them dramatically more resistant to degradation by serum nucleases than incorporation of 2-amino-3-methyl-5-(2?-deoxy-?-D-ribofuranosyl)pyridine (dMAP) or dC.



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Published date: 20 April 2011
Organisations: Centre for Biological Sciences

Identifiers

Local EPrints ID: 206537
URI: http://eprints.soton.ac.uk/id/eprint/206537
ISSN: 2040-2503
PURE UUID: 8c6a0d8b-7544-4895-896d-2af8781a7862
ORCID for Keith R. Fox: ORCID iD orcid.org/0000-0002-2925-7315

Catalogue record

Date deposited: 22 Dec 2011 15:22
Last modified: 03 Dec 2019 02:07

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