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Serge L. Beaucage - One of the best experts on this subject based on the ideXlab platform.
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The 3-(N-tert-butylcarboxamido)-1-Propyl Group as an attractive phosphate/thiophosphate protecting Group for solid-phase oligodeoxyribonucleotide synthesis.
The Journal of organic chemistry, 2002Co-Authors: Andrzej Wilk, Marcin K. Chmielewski, Andrzej Grajkowski, Lawrence R. Phillips, Serge L. BeaucageAbstract:Among the various phosphate/thiophosphate protecting Groups suitable for solid-phase oligonucleotide synthesis, the 3-(N-tert-butylcarboxamido)-1-Propyl Group is one of the most convenient, as it can be readily removed, as needed, under thermolytic conditions at neutral pH. The deprotection reaction proceeds rapidly (t(1/2) approximately 100 s) through an intramolecular cyclodeesterification reaction involving the amide function and the release of the phosphate/thiophosphate Group as a 2-(tert-butylimino)tetrahydrofuran salt. Incorporation of the 3-(N-tert-butylcarboxamido)-1-Propyl Group into the deoxyribonucleoside phosphoramidites 1a-d is achieved using inexpensive raw materials. The coupling efficiency of 1a-d in the solid-phase synthesis of d(ATCCGTAGCTAAGGTCATGC) and its phosphorothioate analogue is comparable to that of commercial 2-cyanoethyl deoxyribonucleoside phosphoramidites. These oligonucleotides were phosphate/thiophosphate-deprotected within 30 min upon heating at 90 degrees C in Phosphate-Buffered Saline (PBS buffer, pH 7.2). Since no detectable nucleobase modification or significant phosphorothioate desulfurization occurs, the 3-(N-tert-butylcarboxamido)-1-Propyl Group represents an attractive alternative to the 2-cyanoethyl Group toward the large-scale preparation of therapeutic oligonucleotides.
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the 3 n tert butylcarboxamido 1 Propyl Group as an attractive phosphate thiophosphate protecting Group for solid phase oligodeoxyribonucleotide synthesis
Journal of Organic Chemistry, 2002Co-Authors: Andrzej Wilk, Marcin K. Chmielewski, Andrzej Grajkowski, Lawrence R. Phillips, Serge L. BeaucageAbstract:Among the various phosphate/thiophosphate protecting Groups suitable for solid-phase oligonucleotide synthesis, the 3-(N-tert-butylcarboxamido)-1-Propyl Group is one of the most convenient, as it can be readily removed, as needed, under thermolytic conditions at neutral pH. The deprotection reaction proceeds rapidly (t(1/2) approximately 100 s) through an intramolecular cyclodeesterification reaction involving the amide function and the release of the phosphate/thiophosphate Group as a 2-(tert-butylimino)tetrahydrofuran salt. Incorporation of the 3-(N-tert-butylcarboxamido)-1-Propyl Group into the deoxyribonucleoside phosphoramidites 1a-d is achieved using inexpensive raw materials. The coupling efficiency of 1a-d in the solid-phase synthesis of d(ATCCGTAGCTAAGGTCATGC) and its phosphorothioate analogue is comparable to that of commercial 2-cyanoethyl deoxyribonucleoside phosphoramidites. These oligonucleotides were phosphate/thiophosphate-deprotected within 30 min upon heating at 90 degrees C in Phosphate-Buffered Saline (PBS buffer, pH 7.2). Since no detectable nucleobase modification or significant phosphorothioate desulfurization occurs, the 3-(N-tert-butylcarboxamido)-1-Propyl Group represents an attractive alternative to the 2-cyanoethyl Group toward the large-scale preparation of therapeutic oligonucleotides.
Andrzej Wilk - One of the best experts on this subject based on the ideXlab platform.
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The 3-(N-tert-butylcarboxamido)-1-Propyl Group as an attractive phosphate/thiophosphate protecting Group for solid-phase oligodeoxyribonucleotide synthesis.
The Journal of organic chemistry, 2002Co-Authors: Andrzej Wilk, Marcin K. Chmielewski, Andrzej Grajkowski, Lawrence R. Phillips, Serge L. BeaucageAbstract:Among the various phosphate/thiophosphate protecting Groups suitable for solid-phase oligonucleotide synthesis, the 3-(N-tert-butylcarboxamido)-1-Propyl Group is one of the most convenient, as it can be readily removed, as needed, under thermolytic conditions at neutral pH. The deprotection reaction proceeds rapidly (t(1/2) approximately 100 s) through an intramolecular cyclodeesterification reaction involving the amide function and the release of the phosphate/thiophosphate Group as a 2-(tert-butylimino)tetrahydrofuran salt. Incorporation of the 3-(N-tert-butylcarboxamido)-1-Propyl Group into the deoxyribonucleoside phosphoramidites 1a-d is achieved using inexpensive raw materials. The coupling efficiency of 1a-d in the solid-phase synthesis of d(ATCCGTAGCTAAGGTCATGC) and its phosphorothioate analogue is comparable to that of commercial 2-cyanoethyl deoxyribonucleoside phosphoramidites. These oligonucleotides were phosphate/thiophosphate-deprotected within 30 min upon heating at 90 degrees C in Phosphate-Buffered Saline (PBS buffer, pH 7.2). Since no detectable nucleobase modification or significant phosphorothioate desulfurization occurs, the 3-(N-tert-butylcarboxamido)-1-Propyl Group represents an attractive alternative to the 2-cyanoethyl Group toward the large-scale preparation of therapeutic oligonucleotides.
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the 3 n tert butylcarboxamido 1 Propyl Group as an attractive phosphate thiophosphate protecting Group for solid phase oligodeoxyribonucleotide synthesis
Journal of Organic Chemistry, 2002Co-Authors: Andrzej Wilk, Marcin K. Chmielewski, Andrzej Grajkowski, Lawrence R. Phillips, Serge L. BeaucageAbstract:Among the various phosphate/thiophosphate protecting Groups suitable for solid-phase oligonucleotide synthesis, the 3-(N-tert-butylcarboxamido)-1-Propyl Group is one of the most convenient, as it can be readily removed, as needed, under thermolytic conditions at neutral pH. The deprotection reaction proceeds rapidly (t(1/2) approximately 100 s) through an intramolecular cyclodeesterification reaction involving the amide function and the release of the phosphate/thiophosphate Group as a 2-(tert-butylimino)tetrahydrofuran salt. Incorporation of the 3-(N-tert-butylcarboxamido)-1-Propyl Group into the deoxyribonucleoside phosphoramidites 1a-d is achieved using inexpensive raw materials. The coupling efficiency of 1a-d in the solid-phase synthesis of d(ATCCGTAGCTAAGGTCATGC) and its phosphorothioate analogue is comparable to that of commercial 2-cyanoethyl deoxyribonucleoside phosphoramidites. These oligonucleotides were phosphate/thiophosphate-deprotected within 30 min upon heating at 90 degrees C in Phosphate-Buffered Saline (PBS buffer, pH 7.2). Since no detectable nucleobase modification or significant phosphorothioate desulfurization occurs, the 3-(N-tert-butylcarboxamido)-1-Propyl Group represents an attractive alternative to the 2-cyanoethyl Group toward the large-scale preparation of therapeutic oligonucleotides.
Lawrence R. Phillips - One of the best experts on this subject based on the ideXlab platform.
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The 3-(N-tert-butylcarboxamido)-1-Propyl Group as an attractive phosphate/thiophosphate protecting Group for solid-phase oligodeoxyribonucleotide synthesis.
The Journal of organic chemistry, 2002Co-Authors: Andrzej Wilk, Marcin K. Chmielewski, Andrzej Grajkowski, Lawrence R. Phillips, Serge L. BeaucageAbstract:Among the various phosphate/thiophosphate protecting Groups suitable for solid-phase oligonucleotide synthesis, the 3-(N-tert-butylcarboxamido)-1-Propyl Group is one of the most convenient, as it can be readily removed, as needed, under thermolytic conditions at neutral pH. The deprotection reaction proceeds rapidly (t(1/2) approximately 100 s) through an intramolecular cyclodeesterification reaction involving the amide function and the release of the phosphate/thiophosphate Group as a 2-(tert-butylimino)tetrahydrofuran salt. Incorporation of the 3-(N-tert-butylcarboxamido)-1-Propyl Group into the deoxyribonucleoside phosphoramidites 1a-d is achieved using inexpensive raw materials. The coupling efficiency of 1a-d in the solid-phase synthesis of d(ATCCGTAGCTAAGGTCATGC) and its phosphorothioate analogue is comparable to that of commercial 2-cyanoethyl deoxyribonucleoside phosphoramidites. These oligonucleotides were phosphate/thiophosphate-deprotected within 30 min upon heating at 90 degrees C in Phosphate-Buffered Saline (PBS buffer, pH 7.2). Since no detectable nucleobase modification or significant phosphorothioate desulfurization occurs, the 3-(N-tert-butylcarboxamido)-1-Propyl Group represents an attractive alternative to the 2-cyanoethyl Group toward the large-scale preparation of therapeutic oligonucleotides.
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the 3 n tert butylcarboxamido 1 Propyl Group as an attractive phosphate thiophosphate protecting Group for solid phase oligodeoxyribonucleotide synthesis
Journal of Organic Chemistry, 2002Co-Authors: Andrzej Wilk, Marcin K. Chmielewski, Andrzej Grajkowski, Lawrence R. Phillips, Serge L. BeaucageAbstract:Among the various phosphate/thiophosphate protecting Groups suitable for solid-phase oligonucleotide synthesis, the 3-(N-tert-butylcarboxamido)-1-Propyl Group is one of the most convenient, as it can be readily removed, as needed, under thermolytic conditions at neutral pH. The deprotection reaction proceeds rapidly (t(1/2) approximately 100 s) through an intramolecular cyclodeesterification reaction involving the amide function and the release of the phosphate/thiophosphate Group as a 2-(tert-butylimino)tetrahydrofuran salt. Incorporation of the 3-(N-tert-butylcarboxamido)-1-Propyl Group into the deoxyribonucleoside phosphoramidites 1a-d is achieved using inexpensive raw materials. The coupling efficiency of 1a-d in the solid-phase synthesis of d(ATCCGTAGCTAAGGTCATGC) and its phosphorothioate analogue is comparable to that of commercial 2-cyanoethyl deoxyribonucleoside phosphoramidites. These oligonucleotides were phosphate/thiophosphate-deprotected within 30 min upon heating at 90 degrees C in Phosphate-Buffered Saline (PBS buffer, pH 7.2). Since no detectable nucleobase modification or significant phosphorothioate desulfurization occurs, the 3-(N-tert-butylcarboxamido)-1-Propyl Group represents an attractive alternative to the 2-cyanoethyl Group toward the large-scale preparation of therapeutic oligonucleotides.
Andrzej Grajkowski - One of the best experts on this subject based on the ideXlab platform.
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The 3-(N-tert-butylcarboxamido)-1-Propyl Group as an attractive phosphate/thiophosphate protecting Group for solid-phase oligodeoxyribonucleotide synthesis.
The Journal of organic chemistry, 2002Co-Authors: Andrzej Wilk, Marcin K. Chmielewski, Andrzej Grajkowski, Lawrence R. Phillips, Serge L. BeaucageAbstract:Among the various phosphate/thiophosphate protecting Groups suitable for solid-phase oligonucleotide synthesis, the 3-(N-tert-butylcarboxamido)-1-Propyl Group is one of the most convenient, as it can be readily removed, as needed, under thermolytic conditions at neutral pH. The deprotection reaction proceeds rapidly (t(1/2) approximately 100 s) through an intramolecular cyclodeesterification reaction involving the amide function and the release of the phosphate/thiophosphate Group as a 2-(tert-butylimino)tetrahydrofuran salt. Incorporation of the 3-(N-tert-butylcarboxamido)-1-Propyl Group into the deoxyribonucleoside phosphoramidites 1a-d is achieved using inexpensive raw materials. The coupling efficiency of 1a-d in the solid-phase synthesis of d(ATCCGTAGCTAAGGTCATGC) and its phosphorothioate analogue is comparable to that of commercial 2-cyanoethyl deoxyribonucleoside phosphoramidites. These oligonucleotides were phosphate/thiophosphate-deprotected within 30 min upon heating at 90 degrees C in Phosphate-Buffered Saline (PBS buffer, pH 7.2). Since no detectable nucleobase modification or significant phosphorothioate desulfurization occurs, the 3-(N-tert-butylcarboxamido)-1-Propyl Group represents an attractive alternative to the 2-cyanoethyl Group toward the large-scale preparation of therapeutic oligonucleotides.
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the 3 n tert butylcarboxamido 1 Propyl Group as an attractive phosphate thiophosphate protecting Group for solid phase oligodeoxyribonucleotide synthesis
Journal of Organic Chemistry, 2002Co-Authors: Andrzej Wilk, Marcin K. Chmielewski, Andrzej Grajkowski, Lawrence R. Phillips, Serge L. BeaucageAbstract:Among the various phosphate/thiophosphate protecting Groups suitable for solid-phase oligonucleotide synthesis, the 3-(N-tert-butylcarboxamido)-1-Propyl Group is one of the most convenient, as it can be readily removed, as needed, under thermolytic conditions at neutral pH. The deprotection reaction proceeds rapidly (t(1/2) approximately 100 s) through an intramolecular cyclodeesterification reaction involving the amide function and the release of the phosphate/thiophosphate Group as a 2-(tert-butylimino)tetrahydrofuran salt. Incorporation of the 3-(N-tert-butylcarboxamido)-1-Propyl Group into the deoxyribonucleoside phosphoramidites 1a-d is achieved using inexpensive raw materials. The coupling efficiency of 1a-d in the solid-phase synthesis of d(ATCCGTAGCTAAGGTCATGC) and its phosphorothioate analogue is comparable to that of commercial 2-cyanoethyl deoxyribonucleoside phosphoramidites. These oligonucleotides were phosphate/thiophosphate-deprotected within 30 min upon heating at 90 degrees C in Phosphate-Buffered Saline (PBS buffer, pH 7.2). Since no detectable nucleobase modification or significant phosphorothioate desulfurization occurs, the 3-(N-tert-butylcarboxamido)-1-Propyl Group represents an attractive alternative to the 2-cyanoethyl Group toward the large-scale preparation of therapeutic oligonucleotides.
Marcin K. Chmielewski - One of the best experts on this subject based on the ideXlab platform.
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The 3-(N-tert-butylcarboxamido)-1-Propyl Group as an attractive phosphate/thiophosphate protecting Group for solid-phase oligodeoxyribonucleotide synthesis.
The Journal of organic chemistry, 2002Co-Authors: Andrzej Wilk, Marcin K. Chmielewski, Andrzej Grajkowski, Lawrence R. Phillips, Serge L. BeaucageAbstract:Among the various phosphate/thiophosphate protecting Groups suitable for solid-phase oligonucleotide synthesis, the 3-(N-tert-butylcarboxamido)-1-Propyl Group is one of the most convenient, as it can be readily removed, as needed, under thermolytic conditions at neutral pH. The deprotection reaction proceeds rapidly (t(1/2) approximately 100 s) through an intramolecular cyclodeesterification reaction involving the amide function and the release of the phosphate/thiophosphate Group as a 2-(tert-butylimino)tetrahydrofuran salt. Incorporation of the 3-(N-tert-butylcarboxamido)-1-Propyl Group into the deoxyribonucleoside phosphoramidites 1a-d is achieved using inexpensive raw materials. The coupling efficiency of 1a-d in the solid-phase synthesis of d(ATCCGTAGCTAAGGTCATGC) and its phosphorothioate analogue is comparable to that of commercial 2-cyanoethyl deoxyribonucleoside phosphoramidites. These oligonucleotides were phosphate/thiophosphate-deprotected within 30 min upon heating at 90 degrees C in Phosphate-Buffered Saline (PBS buffer, pH 7.2). Since no detectable nucleobase modification or significant phosphorothioate desulfurization occurs, the 3-(N-tert-butylcarboxamido)-1-Propyl Group represents an attractive alternative to the 2-cyanoethyl Group toward the large-scale preparation of therapeutic oligonucleotides.
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the 3 n tert butylcarboxamido 1 Propyl Group as an attractive phosphate thiophosphate protecting Group for solid phase oligodeoxyribonucleotide synthesis
Journal of Organic Chemistry, 2002Co-Authors: Andrzej Wilk, Marcin K. Chmielewski, Andrzej Grajkowski, Lawrence R. Phillips, Serge L. BeaucageAbstract:Among the various phosphate/thiophosphate protecting Groups suitable for solid-phase oligonucleotide synthesis, the 3-(N-tert-butylcarboxamido)-1-Propyl Group is one of the most convenient, as it can be readily removed, as needed, under thermolytic conditions at neutral pH. The deprotection reaction proceeds rapidly (t(1/2) approximately 100 s) through an intramolecular cyclodeesterification reaction involving the amide function and the release of the phosphate/thiophosphate Group as a 2-(tert-butylimino)tetrahydrofuran salt. Incorporation of the 3-(N-tert-butylcarboxamido)-1-Propyl Group into the deoxyribonucleoside phosphoramidites 1a-d is achieved using inexpensive raw materials. The coupling efficiency of 1a-d in the solid-phase synthesis of d(ATCCGTAGCTAAGGTCATGC) and its phosphorothioate analogue is comparable to that of commercial 2-cyanoethyl deoxyribonucleoside phosphoramidites. These oligonucleotides were phosphate/thiophosphate-deprotected within 30 min upon heating at 90 degrees C in Phosphate-Buffered Saline (PBS buffer, pH 7.2). Since no detectable nucleobase modification or significant phosphorothioate desulfurization occurs, the 3-(N-tert-butylcarboxamido)-1-Propyl Group represents an attractive alternative to the 2-cyanoethyl Group toward the large-scale preparation of therapeutic oligonucleotides.