Sulfonamide bearing oligonucleotides: Simple synthesis and efficient RNA recognition

P. Kumar, N. Chandak, P. Nielsen, P. K. Sharma

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

Four pyrimidine nucleosides wherein a benzensulfonamide group is linked to the C-5 position of the uracil nucleobase through a triazolyl or an alkynyl linker were prepared by Cu(I)-assisted azide-alkyne cycloadditions (CuAAC) or Sonogashira reactions, respectively, and incorporated into oligonucleotides. Efficient pi-pi-stacking between two or more phenyltriazoles in the major groove was found to increase the thermal stability of a DNA: RNA duplex significantly. On the other hand, the alkynyl group was not as efficient in stacking as the triazolyl group. No effect of positional orientation of the sulfonamide group on the stacking efficiency was observed, and the most stable DNA: RNA duplex contained four consecutive sulfonamide substituted phenyltriazole moieties in the major groove. (C) 2012 Elsevier Ltd. All rights reserved.
OriginalsprogEngelsk
TidsskriftBioorganic & Medicinal Chemistry
Vol/bind20
Udgave nummer12
Sider (fra-til)3843-3849
Antal sider7
ISSN0968-0896
DOI
StatusUdgivet - 2012

Citer dette

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abstract = "Four pyrimidine nucleosides wherein a benzensulfonamide group is linked to the C-5 position of the uracil nucleobase through a triazolyl or an alkynyl linker were prepared by Cu(I)-assisted azide-alkyne cycloadditions (CuAAC) or Sonogashira reactions, respectively, and incorporated into oligonucleotides. Efficient pi-pi-stacking between two or more phenyltriazoles in the major groove was found to increase the thermal stability of a DNA: RNA duplex significantly. On the other hand, the alkynyl group was not as efficient in stacking as the triazolyl group. No effect of positional orientation of the sulfonamide group on the stacking efficiency was observed, and the most stable DNA: RNA duplex contained four consecutive sulfonamide substituted phenyltriazole moieties in the major groove. (C) 2012 Elsevier Ltd. All rights reserved.",
author = "P. Kumar and N. Chandak and P. Nielsen and Sharma, {P. K.}",
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Sulfonamide bearing oligonucleotides: Simple synthesis and efficient RNA recognition. / Kumar, P.; Chandak, N.; Nielsen, P.; Sharma, P. K.

I: Bioorganic & Medicinal Chemistry, Bind 20, Nr. 12, 2012, s. 3843-3849.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - Sulfonamide bearing oligonucleotides: Simple synthesis and efficient RNA recognition

AU - Kumar, P.

AU - Chandak, N.

AU - Nielsen, P.

AU - Sharma, P. K.

PY - 2012

Y1 - 2012

N2 - Four pyrimidine nucleosides wherein a benzensulfonamide group is linked to the C-5 position of the uracil nucleobase through a triazolyl or an alkynyl linker were prepared by Cu(I)-assisted azide-alkyne cycloadditions (CuAAC) or Sonogashira reactions, respectively, and incorporated into oligonucleotides. Efficient pi-pi-stacking between two or more phenyltriazoles in the major groove was found to increase the thermal stability of a DNA: RNA duplex significantly. On the other hand, the alkynyl group was not as efficient in stacking as the triazolyl group. No effect of positional orientation of the sulfonamide group on the stacking efficiency was observed, and the most stable DNA: RNA duplex contained four consecutive sulfonamide substituted phenyltriazole moieties in the major groove. (C) 2012 Elsevier Ltd. All rights reserved.

AB - Four pyrimidine nucleosides wherein a benzensulfonamide group is linked to the C-5 position of the uracil nucleobase through a triazolyl or an alkynyl linker were prepared by Cu(I)-assisted azide-alkyne cycloadditions (CuAAC) or Sonogashira reactions, respectively, and incorporated into oligonucleotides. Efficient pi-pi-stacking between two or more phenyltriazoles in the major groove was found to increase the thermal stability of a DNA: RNA duplex significantly. On the other hand, the alkynyl group was not as efficient in stacking as the triazolyl group. No effect of positional orientation of the sulfonamide group on the stacking efficiency was observed, and the most stable DNA: RNA duplex contained four consecutive sulfonamide substituted phenyltriazole moieties in the major groove. (C) 2012 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.bmc.2012.04.036

DO - 10.1016/j.bmc.2012.04.036

M3 - Journal article

VL - 20

SP - 3843

EP - 3849

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

SN - 0968-0896

IS - 12

ER -