Duplex stabilities of phosphorothioate, methylphosphonate, and RNA analogs of two DNA 14-mers.
Identifieur interne : 000482 ( Ncbi/Checkpoint ); précédent : 000481; suivant : 000483Duplex stabilities of phosphorothioate, methylphosphonate, and RNA analogs of two DNA 14-mers.
Auteurs : L. Kibler-Herzog ; G. Zon ; B. Uznanski ; G. Whittier ; W D WilsonSource :
- Nucleic acids research [ 0305-1048 ] ; 1991.
Descripteurs français
- KwdFr :
- MESH :
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : DNA, Organophosphorus Compounds, RNA, Thionucleotides.
- Base Sequence, Molecular Sequence Data, Nucleic Acid Heteroduplexes, Spectrophotometry, Ultraviolet, Temperature.
Abstract
The duplex stabilities of various phosphorothioate, methylphosphonate, RNA and 2'-OCH3 RNA analogs of two self-complementary DNA 14-mers are compared. Phosphorothioate and/or methylphosphonate analogs of the two sequences d(TAATTAATTAATTA) [D1] and d(TAGCTAATTAGCTA) [D2] differ in the number, position, or chirality (at the 5' terminal linkage) of the modified phosphates. Phosphorothioate derivatives of D1 are found to be less destabilized when the linkage modified is between adenines rather than between thymines. Surprisingly, no base sequence effect on duplex stabilization is observed for any methylphosphonate derivatives of D1 or D2. Highly modified phosphorothioates or methylphosphonates are less stable than their partially modified counterparts which are less stable than the unmodified parent compounds. The 'normal' (2'-OH) RNA analog of duplex D1 is slightly destabilized, whereas the 2'-OCH3 RNA derivative is significantly stabilized relative to the unmodified DNA. For the D1 sequence, at approximately physiological salt concentration, the order of duplex stability is 2'-OCH3 RNA greater than unmodified DNA greater than 'normal' RNA greater than methylphosphonate DNA greater than phosphorothioate DNA. D2 and the various D2 methylphosphonate analogs investigated all formed hairpin conformations at low salt concentrations.
DOI: 10.1093/nar/19.11.2979
PubMed: 1711677
Affiliations:
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Kibler-Herzog</name><affiliation><nlm:affiliation>Department of Chemistry, Georgia State University, Atlanta.</nlm:affiliation><wicri:noCountry code="subField">Atlanta</wicri:noCountry></affiliation></author><author><name sortKey="Zon, G" sort="Zon, G" uniqKey="Zon G" first="G" last="Zon">G. Zon</name></author><author><name sortKey="Uznanski, B" sort="Uznanski, B" uniqKey="Uznanski B" first="B" last="Uznanski">B. Uznanski</name></author><author><name sortKey="Whittier, G" sort="Whittier, G" uniqKey="Whittier G" first="G" last="Whittier">G. Whittier</name></author><author><name sortKey="Wilson, W D" sort="Wilson, W D" uniqKey="Wilson W" first="W D" last="Wilson">W D Wilson</name></author></analytic><series><title level="j">Nucleic acids research</title><idno type="ISSN">0305-1048</idno><imprint><date when="1991" type="published">1991</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Base Sequence</term><term>DNA (chemistry)</term><term>Molecular Sequence Data</term><term>Nucleic Acid Heteroduplexes</term><term>Organophosphorus Compounds (chemistry)</term><term>RNA (chemistry)</term><term>Spectrophotometry, Ultraviolet</term><term>Temperature</term><term>Thionucleotides (chemistry)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>ADN ()</term><term>ARN ()</term><term>Composés organiques du phosphore ()</term><term>Données de séquences moléculaires</term><term>Hétéroduplexes d'acides nucléiques</term><term>Spectrophotométrie UV</term><term>Séquence nucléotidique</term><term>Température</term><term>Thionucléotides ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>DNA</term><term>Organophosphorus Compounds</term><term>RNA</term><term>Thionucleotides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Base Sequence</term><term>Molecular Sequence Data</term><term>Nucleic Acid Heteroduplexes</term><term>Spectrophotometry, Ultraviolet</term><term>Temperature</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>ADN</term><term>ARN</term><term>Composés organiques du phosphore</term><term>Données de séquences moléculaires</term><term>Hétéroduplexes d'acides nucléiques</term><term>Spectrophotométrie UV</term><term>Séquence nucléotidique</term><term>Température</term><term>Thionucléotides</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The duplex stabilities of various phosphorothioate, methylphosphonate, RNA and 2'-OCH3 RNA analogs of two self-complementary DNA 14-mers are compared. Phosphorothioate and/or methylphosphonate analogs of the two sequences d(TAATTAATTAATTA) [D1] and d(TAGCTAATTAGCTA) [D2] differ in the number, position, or chirality (at the 5' terminal linkage) of the modified phosphates. Phosphorothioate derivatives of D1 are found to be less destabilized when the linkage modified is between adenines rather than between thymines. Surprisingly, no base sequence effect on duplex stabilization is observed for any methylphosphonate derivatives of D1 or D2. Highly modified phosphorothioates or methylphosphonates are less stable than their partially modified counterparts which are less stable than the unmodified parent compounds. The 'normal' (2'-OH) RNA analog of duplex D1 is slightly destabilized, whereas the 2'-OCH3 RNA derivative is significantly stabilized relative to the unmodified DNA. For the D1 sequence, at approximately physiological salt concentration, the order of duplex stability is 2'-OCH3 RNA greater than unmodified DNA greater than 'normal' RNA greater than methylphosphonate DNA greater than phosphorothioate DNA. D2 and the various D2 methylphosphonate analogs investigated all formed hairpin conformations at low salt concentrations.</div></front></TEI><affiliations><list></list><tree><noCountry><name sortKey="Kibler Herzog, L" sort="Kibler Herzog, L" uniqKey="Kibler Herzog L" first="L" last="Kibler-Herzog">L. Kibler-Herzog</name><name sortKey="Uznanski, B" sort="Uznanski, B" uniqKey="Uznanski B" first="B" last="Uznanski">B. Uznanski</name><name sortKey="Whittier, G" sort="Whittier, G" uniqKey="Whittier G" first="G" last="Whittier">G. Whittier</name><name sortKey="Wilson, W D" sort="Wilson, W D" uniqKey="Wilson W" first="W D" last="Wilson">W D Wilson</name><name sortKey="Zon, G" sort="Zon, G" uniqKey="Zon G" first="G" last="Zon">G. 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