Synthesis of oligodeoxynucleotides containing 2-thiopyrimidine residues--a new protection scheme.
Identifieur interne : 004261 ( Main/Exploration ); précédent : 004260; suivant : 004262Synthesis of oligodeoxynucleotides containing 2-thiopyrimidine residues--a new protection scheme.
Auteurs : R G Kuimelis ; K P NambiarSource :
- Nucleic acids research [ 0305-1048 ] ; 1994.
Descripteurs français
- KwdFr :
- 4-Thiouridine (), 4-Thiouridine (analogues et dérivés), Dichroïsme circulaire, Données de séquences moléculaires, Dénaturation d'acide nucléique, Oligodésoxyribonucléotides (), Oligodésoxyribonucléotides (isolement et purification), Oligodésoxyribonucléotides (synthèse chimique), Structure moléculaire, Séquence nucléotidique, Thionucléotides (), Thymidine (), Thymidine (analogues et dérivés).
- MESH :
- analogues et dérivés : 4-Thiouridine, Thymidine.
- isolement et purification : Oligodésoxyribonucléotides.
- synthèse chimique : Oligodésoxyribonucléotides.
- 4-Thiouridine, Dichroïsme circulaire, Données de séquences moléculaires, Dénaturation d'acide nucléique, Oligodésoxyribonucléotides, Structure moléculaire, Séquence nucléotidique, Thionucléotides, Thymidine.
English descriptors
- KwdEn :
- Base Sequence, Circular Dichroism, Molecular Sequence Data, Molecular Structure, Nucleic Acid Denaturation, Oligodeoxyribonucleotides (chemical synthesis), Oligodeoxyribonucleotides (chemistry), Oligodeoxyribonucleotides (isolation & purification), Thionucleotides (chemistry), Thiouridine (analogs & derivatives), Thiouridine (chemistry), Thymidine (analogs & derivatives), Thymidine (chemistry).
- MESH :
- chemical , analogs & derivatives : Thiouridine, Thymidine.
- chemical , chemical synthesis : Oligodeoxyribonucleotides.
- chemical , chemistry : Oligodeoxyribonucleotides, Thionucleotides, Thiouridine, Thymidine.
- chemical , isolation & purification : Oligodeoxyribonucleotides.
- Base Sequence, Circular Dichroism, Molecular Sequence Data, Molecular Structure, Nucleic Acid Denaturation.
Abstract
A method is described for the incorporation of 2'-deoxy-2-thiouridine (dS2U) and 2'-deoxy-2-thiothymidine (dS2T) into oligodeoxynucleotides at predetermined positions. This requires N3 or O4-acylation of dS2U and dS2T with toluoyl chloride. These base-protected thiopyrimidines are completely stable toward the aqueous iodine oxidation reagent used in the phosphoramidite DNA synthesis method. The toluoyl protecting group is removed during the standard post-synthetic ammonia treatment. This novel protection strategy allows dS2U and dS2T to be efficiently incorporated into oligodeoxynucleotides at predetermined sites without the usual problem of desulfurization and decomposition. Several 14-mers containing the Eco-RI recognition site (dGGCGGAAXXCCGCC and dGGCGGAAXXCGCGG, where X represents dT, dS2U or dS2T) have been synthesized and characterized by base composition, thermal denaturation, CD spectroscopy and endonuclease substrate activity.
DOI: 10.1093/nar/22.8.1429
PubMed: 8190635
Affiliations:
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Le document en format XML
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Kuimelis</name><affiliation><nlm:affiliation>Department of Chemistry, University of California, Davis 95616.</nlm:affiliation><wicri:noCountry code="subField">Davis 95616</wicri:noCountry></affiliation></author><author><name sortKey="Nambiar, K P" sort="Nambiar, K P" uniqKey="Nambiar K" first="K P" last="Nambiar">K P Nambiar</name></author></analytic><series><title level="j">Nucleic acids research</title><idno type="ISSN">0305-1048</idno><imprint><date when="1994" type="published">1994</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Base Sequence</term><term>Circular Dichroism</term><term>Molecular Sequence Data</term><term>Molecular Structure</term><term>Nucleic Acid Denaturation</term><term>Oligodeoxyribonucleotides (chemical synthesis)</term><term>Oligodeoxyribonucleotides (chemistry)</term><term>Oligodeoxyribonucleotides (isolation & purification)</term><term>Thionucleotides (chemistry)</term><term>Thiouridine (analogs & derivatives)</term><term>Thiouridine (chemistry)</term><term>Thymidine (analogs & derivatives)</term><term>Thymidine (chemistry)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>4-Thiouridine ()</term><term>4-Thiouridine (analogues et dérivés)</term><term>Dichroïsme circulaire</term><term>Données de séquences moléculaires</term><term>Dénaturation d'acide nucléique</term><term>Oligodésoxyribonucléotides ()</term><term>Oligodésoxyribonucléotides (isolement et purification)</term><term>Oligodésoxyribonucléotides (synthèse chimique)</term><term>Structure moléculaire</term><term>Séquence nucléotidique</term><term>Thionucléotides ()</term><term>Thymidine ()</term><term>Thymidine (analogues et dérivés)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Thiouridine</term><term>Thymidine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Oligodeoxyribonucleotides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Oligodeoxyribonucleotides</term><term>Thionucleotides</term><term>Thiouridine</term><term>Thymidine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Oligodeoxyribonucleotides</term></keywords><keywords scheme="MESH" qualifier="analogues et dérivés" xml:lang="fr"><term>4-Thiouridine</term><term>Thymidine</term></keywords><keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr"><term>Oligodésoxyribonucléotides</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Oligodésoxyribonucléotides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Base Sequence</term><term>Circular Dichroism</term><term>Molecular Sequence Data</term><term>Molecular Structure</term><term>Nucleic Acid Denaturation</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>4-Thiouridine</term><term>Dichroïsme circulaire</term><term>Données de séquences moléculaires</term><term>Dénaturation d'acide nucléique</term><term>Oligodésoxyribonucléotides</term><term>Structure moléculaire</term><term>Séquence nucléotidique</term><term>Thionucléotides</term><term>Thymidine</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A method is described for the incorporation of 2'-deoxy-2-thiouridine (dS2U) and 2'-deoxy-2-thiothymidine (dS2T) into oligodeoxynucleotides at predetermined positions. This requires N3 or O4-acylation of dS2U and dS2T with toluoyl chloride. These base-protected thiopyrimidines are completely stable toward the aqueous iodine oxidation reagent used in the phosphoramidite DNA synthesis method. The toluoyl protecting group is removed during the standard post-synthetic ammonia treatment. This novel protection strategy allows dS2U and dS2T to be efficiently incorporated into oligodeoxynucleotides at predetermined sites without the usual problem of desulfurization and decomposition. Several 14-mers containing the Eco-RI recognition site (dGGCGGAAXXCCGCC and dGGCGGAAXXCGCGG, where X represents dT, dS2U or dS2T) have been synthesized and characterized by base composition, thermal denaturation, CD spectroscopy and endonuclease substrate activity.</div></front></TEI><affiliations><list></list><tree><noCountry><name sortKey="Kuimelis, R G" sort="Kuimelis, R G" uniqKey="Kuimelis R" first="R G" last="Kuimelis">R G Kuimelis</name><name sortKey="Nambiar, K P" sort="Nambiar, K P" uniqKey="Nambiar K" first="K P" last="Nambiar">K P Nambiar</name></noCountry></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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