Chemical synthesis of selenium-modified oligoribonucleotides and their enzymatic ligation leading to an U6 SnRNA stem-loop segment.
Identifieur interne : 002281 ( PubMed/Checkpoint ); précédent : 002280; suivant : 002282Chemical synthesis of selenium-modified oligoribonucleotides and their enzymatic ligation leading to an U6 SnRNA stem-loop segment.
Auteurs : Claudia Höbartner [Autriche] ; Ronald MicuraSource :
- Journal of the American Chemical Society [ 0002-7863 ] ; 2004.
Descripteurs français
- KwdFr :
- ARN (), ARN (synthèse chimique), Composés organiques du phosphore (), Composés organiques du phosphore (synthèse chimique), Composés organiques du sélénium (), Composés organiques du sélénium (synthèse chimique), Conformation d'acide nucléique, Cristallographie aux rayons X, Données de séquences moléculaires, Oligoribonucléotides (), Oligoribonucléotides (synthèse chimique), Petit ARN nucléaire (), Séquence nucléotidique.
- MESH :
- synthèse chimique : ARN, Composés organiques du phosphore, Composés organiques du sélénium, Oligoribonucléotides.
- ARN, Composés organiques du phosphore, Composés organiques du sélénium, Conformation d'acide nucléique, Cristallographie aux rayons X, Données de séquences moléculaires, Oligoribonucléotides, Petit ARN nucléaire, Séquence nucléotidique.
English descriptors
- KwdEn :
- Base Sequence, Crystallography, X-Ray, Molecular Sequence Data, Nucleic Acid Conformation, Oligoribonucleotides (chemical synthesis), Oligoribonucleotides (chemistry), Organophosphorus Compounds (chemical synthesis), Organophosphorus Compounds (chemistry), Organoselenium Compounds (chemical synthesis), Organoselenium Compounds (chemistry), RNA (chemical synthesis), RNA (chemistry), RNA, Small Nuclear (chemistry).
- MESH :
- chemical , chemical synthesis : Oligoribonucleotides, Organophosphorus Compounds, Organoselenium Compounds, RNA.
- chemical , chemistry : Oligoribonucleotides, Organophosphorus Compounds, Organoselenium Compounds, RNA, RNA, Small Nuclear.
- Base Sequence, Crystallography, X-Ray, Molecular Sequence Data, Nucleic Acid Conformation.
Abstract
The derivatization of nucleic acids with selenium is highly promising to facilitate nucleic acids structure determination by X-ray crystallography using the multiwavelength anomalous dispersion (MAD) technique. The foundation for such an approach has been laid by Huang, Egli, and co-workers and was exemplified on small DNA duplexes. Here, we present a comprehensive study on the preparation of RNAs containing 2'-Se-methylpyrimidine nucleoside labels. This includes the synthesis of a novel 2'-Se-methylcytidine phosphoramidite 11 and its incorporation into oligoribonucleotides by solid-phase synthesis. Deprotection of the oligonucleotides is achieved in the presence of millimolar amounts of threo-1,4-dimercapto-2,3-butandiol (DTT). With this additive, oxidation products and follow-up side-products are suppressed and acceptable HPLC traces of the crude material are obtained, so far tested for sequences of up to 22-mers. Moreover, an extensive investigation on the enzymatic ligation of the selenium-containing oligoribonucleotides demonstrates the high flexibility of the selenium approach. Our target sequence, an U6 snRNA stem-loop motif comprising all naturally occurring nucleoside modifications beside the Se-label is achieved by ligation using T4 RNA ligase.
DOI: 10.1021/ja038481k
PubMed: 14746483
Affiliations:
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type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Oligoribonucleotides</term><term>Organophosphorus Compounds</term><term>Organoselenium Compounds</term><term>RNA</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Oligoribonucleotides</term><term>Organophosphorus Compounds</term><term>Organoselenium Compounds</term><term>RNA</term><term>RNA, Small Nuclear</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>ARN</term><term>Composés organiques du phosphore</term><term>Composés organiques du sélénium</term><term>Oligoribonucléotides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Base Sequence</term><term>Crystallography, X-Ray</term><term>Molecular Sequence Data</term><term>Nucleic Acid Conformation</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>ARN</term><term>Composés organiques du phosphore</term><term>Composés organiques du sélénium</term><term>Conformation d'acide nucléique</term><term>Cristallographie aux rayons X</term><term>Données de séquences moléculaires</term><term>Oligoribonucléotides</term><term>Petit ARN nucléaire</term><term>Séquence nucléotidique</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The derivatization of nucleic acids with selenium is highly promising to facilitate nucleic acids structure determination by X-ray crystallography using the multiwavelength anomalous dispersion (MAD) technique. The foundation for such an approach has been laid by Huang, Egli, and co-workers and was exemplified on small DNA duplexes. Here, we present a comprehensive study on the preparation of RNAs containing 2'-Se-methylpyrimidine nucleoside labels. This includes the synthesis of a novel 2'-Se-methylcytidine phosphoramidite 11 and its incorporation into oligoribonucleotides by solid-phase synthesis. Deprotection of the oligonucleotides is achieved in the presence of millimolar amounts of threo-1,4-dimercapto-2,3-butandiol (DTT). With this additive, oxidation products and follow-up side-products are suppressed and acceptable HPLC traces of the crude material are obtained, so far tested for sequences of up to 22-mers. Moreover, an extensive investigation on the enzymatic ligation of the selenium-containing oligoribonucleotides demonstrates the high flexibility of the selenium approach. Our target sequence, an U6 snRNA stem-loop motif comprising all naturally occurring nucleoside modifications beside the Se-label is achieved by ligation using T4 RNA ligase.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">14746483</PMID><DateCompleted><Year>2004</Year><Month>05</Month><Day>25</Day></DateCompleted><DateRevised><Year>2006</Year><Month>11</Month><Day>15</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0002-7863</ISSN><JournalIssue CitedMedium="Print"><Volume>126</Volume><Issue>4</Issue><PubDate><Year>2004</Year><Month>Feb</Month><Day>04</Day></PubDate></JournalIssue><Title>Journal of the American Chemical Society</Title><ISOAbbreviation>J. Am. Chem. Soc.</ISOAbbreviation></Journal><ArticleTitle>Chemical synthesis of selenium-modified oligoribonucleotides and their enzymatic ligation leading to an U6 SnRNA stem-loop segment.</ArticleTitle><Pagination><MedlinePgn>1141-9</MedlinePgn></Pagination><Abstract><AbstractText>The derivatization of nucleic acids with selenium is highly promising to facilitate nucleic acids structure determination by X-ray crystallography using the multiwavelength anomalous dispersion (MAD) technique. The foundation for such an approach has been laid by Huang, Egli, and co-workers and was exemplified on small DNA duplexes. Here, we present a comprehensive study on the preparation of RNAs containing 2'-Se-methylpyrimidine nucleoside labels. This includes the synthesis of a novel 2'-Se-methylcytidine phosphoramidite 11 and its incorporation into oligoribonucleotides by solid-phase synthesis. Deprotection of the oligonucleotides is achieved in the presence of millimolar amounts of threo-1,4-dimercapto-2,3-butandiol (DTT). With this additive, oxidation products and follow-up side-products are suppressed and acceptable HPLC traces of the crude material are obtained, so far tested for sequences of up to 22-mers. Moreover, an extensive investigation on the enzymatic ligation of the selenium-containing oligoribonucleotides demonstrates the high flexibility of the selenium approach. 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