Mechanistic studies on the phosphoramidite coupling reaction in oligonucleotide synthesis. I. Evidence for nudeophilic catalysis by tetrazole and rate variations with the phosphorus substituents

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Standard

Mechanistic studies on the phosphoramidite coupling reaction in oligonucleotide synthesis. I. Evidence for nudeophilic catalysis by tetrazole and rate variations with the phosphorus substituents. / Dahl, Bjarne H.; Nielsen, John; Dahl, Otto.

I: Nucleic Acids Research, Bind 15, Nr. 4, 25.02.1987, s. 1729-1743.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Dahl, BH, Nielsen, J & Dahl, O 1987, 'Mechanistic studies on the phosphoramidite coupling reaction in oligonucleotide synthesis. I. Evidence for nudeophilic catalysis by tetrazole and rate variations with the phosphorus substituents', Nucleic Acids Research, bind 15, nr. 4, s. 1729-1743. https://doi.org/10.1093/nar/15.4.1729

APA

Dahl, B. H., Nielsen, J., & Dahl, O. (1987). Mechanistic studies on the phosphoramidite coupling reaction in oligonucleotide synthesis. I. Evidence for nudeophilic catalysis by tetrazole and rate variations with the phosphorus substituents. Nucleic Acids Research, 15(4), 1729-1743. https://doi.org/10.1093/nar/15.4.1729

Vancouver

Dahl BH, Nielsen J, Dahl O. Mechanistic studies on the phosphoramidite coupling reaction in oligonucleotide synthesis. I. Evidence for nudeophilic catalysis by tetrazole and rate variations with the phosphorus substituents. Nucleic Acids Research. 1987 feb. 25;15(4):1729-1743. https://doi.org/10.1093/nar/15.4.1729

Author

Dahl, Bjarne H. ; Nielsen, John ; Dahl, Otto. / Mechanistic studies on the phosphoramidite coupling reaction in oligonucleotide synthesis. I. Evidence for nudeophilic catalysis by tetrazole and rate variations with the phosphorus substituents. I: Nucleic Acids Research. 1987 ; Bind 15, Nr. 4. s. 1729-1743.

Bibtex

@article{cc6a387390b54c5bb5833da412d719da,
title = "Mechanistic studies on the phosphoramidite coupling reaction in oligonucleotide synthesis. I. Evidence for nudeophilic catalysis by tetrazole and rate variations with the phosphorus substituents",
abstract = "Tetrazole catalyzed reactions of a series of phosphoramidites, 5′ -O- DMTdT-3′-O-P(OR 1)NRNR22 (1a-h), with 3′ O-SiBu tPh 2-6-N-benzoyl-dA (2a) in acetonitrite solution have been studied. It is found that the coupling rate depends very much on whether tetrazole is added before or after 2a, and that dialkylammonium tetrazolide salts are inhibitors. These and other facts are evidence that the reactions are subjected to nucleophilic catalysis by tetrazole, in addition to acid catalysis. The rate variations with phosphorus substituents of 1a-h are NEt 2 > NRr12 > N(CH 2CH 2)O > NMePh, and OMe > OCH 2CH 2CN > OCHMeCH 2CN > OCMe 2CH 2CN >> OC 6H 4Cl. The inhibitor properties of dialkylammonium tetrazolides have practical consequences for the efficiency of DNA syntheses, when in situ prepared phosphramidites are used; the same would apply for segmented simultaneous syntheses or syntheses where recycling is performed.",
author = "Dahl, {Bjarne H.} and John Nielsen and Otto Dahl",
year = "1987",
month = feb,
day = "25",
doi = "10.1093/nar/15.4.1729",
language = "English",
volume = "15",
pages = "1729--1743",
journal = "Nucleic Acids Research",
issn = "0305-1048",
publisher = "Oxford University Press",
number = "4",

}

RIS

TY - JOUR

T1 - Mechanistic studies on the phosphoramidite coupling reaction in oligonucleotide synthesis. I. Evidence for nudeophilic catalysis by tetrazole and rate variations with the phosphorus substituents

AU - Dahl, Bjarne H.

AU - Nielsen, John

AU - Dahl, Otto

PY - 1987/2/25

Y1 - 1987/2/25

N2 - Tetrazole catalyzed reactions of a series of phosphoramidites, 5′ -O- DMTdT-3′-O-P(OR 1)NRNR22 (1a-h), with 3′ O-SiBu tPh 2-6-N-benzoyl-dA (2a) in acetonitrite solution have been studied. It is found that the coupling rate depends very much on whether tetrazole is added before or after 2a, and that dialkylammonium tetrazolide salts are inhibitors. These and other facts are evidence that the reactions are subjected to nucleophilic catalysis by tetrazole, in addition to acid catalysis. The rate variations with phosphorus substituents of 1a-h are NEt 2 > NRr12 > N(CH 2CH 2)O > NMePh, and OMe > OCH 2CH 2CN > OCHMeCH 2CN > OCMe 2CH 2CN >> OC 6H 4Cl. The inhibitor properties of dialkylammonium tetrazolides have practical consequences for the efficiency of DNA syntheses, when in situ prepared phosphramidites are used; the same would apply for segmented simultaneous syntheses or syntheses where recycling is performed.

AB - Tetrazole catalyzed reactions of a series of phosphoramidites, 5′ -O- DMTdT-3′-O-P(OR 1)NRNR22 (1a-h), with 3′ O-SiBu tPh 2-6-N-benzoyl-dA (2a) in acetonitrite solution have been studied. It is found that the coupling rate depends very much on whether tetrazole is added before or after 2a, and that dialkylammonium tetrazolide salts are inhibitors. These and other facts are evidence that the reactions are subjected to nucleophilic catalysis by tetrazole, in addition to acid catalysis. The rate variations with phosphorus substituents of 1a-h are NEt 2 > NRr12 > N(CH 2CH 2)O > NMePh, and OMe > OCH 2CH 2CN > OCHMeCH 2CN > OCMe 2CH 2CN >> OC 6H 4Cl. The inhibitor properties of dialkylammonium tetrazolides have practical consequences for the efficiency of DNA syntheses, when in situ prepared phosphramidites are used; the same would apply for segmented simultaneous syntheses or syntheses where recycling is performed.

U2 - 10.1093/nar/15.4.1729

DO - 10.1093/nar/15.4.1729

M3 - Journal article

AN - SCOPUS:0023664045

VL - 15

SP - 1729

EP - 1743

JO - Nucleic Acids Research

JF - Nucleic Acids Research

SN - 0305-1048

IS - 4

ER -

ID: 131115593