1630904

Source:http://linkedlifedata.com/resource/pubmed/id/1630904

Download in:

Switch to

Custom View

Named Graph Language Inference

Statements in which the resource exists as a subject.
Predicate	Object
rdf:type	pubmed:Citation
lifeskim:mentions	umls-concept:C0012854, umls-concept:C0220781, umls-concept:C0871161, umls-concept:C1883254
pubmed:issue	13
pubmed:dateCreated	1992-8-17
pubmed:abstractText	We have investigated the conformations of the hexadeoxyribonucleotide, L-d(CGCGCG) composed of L-deoxyribose, the mirror image molecule of natural D-deoxyribose. In this paper, we report the synthesis of four L-deoxynucleosides and the L-oligonucleotide-ethidium bromide interactions. The L-deoxyribose synthon 9 was synthesized from L-arabinose with an over all yield of 28.5% via the Barton-McCombie reaction. The L-deoxynucleosides were obtained by a glycosylation of appropriate nucleobase derivatives with the 1-chloro sugar 9. After derivatization to nucleoside phosphoramidites, L-deoxycytidine and L-deoxyguanosine were incorporated into a hexadeoxynucleotide, L-d(CGCGCG) by a solid-phase beta-cyanoethylphosphoramidite method. This L-hexanucleotide was resistant to digestion with nuclease P1. The conformations of L-d(CGCGCG) were an exact mirror image of that of the corresponding natural one as described previously, and the conformations of the L-d(CGCGCG)-ethidium bromide complex were also the mirror images of those of the D-d(CGCGCG)-ethidium bromide complex under both low and high salt conditions. These results suggest that ethidium bromide prefers not a right-handed helical sense, but the base-base stacking geometry of the B-form rather than that of the Z-form. Thus, L-DNA would be a useful tool for studying DNA-drug interactions.
pubmed:commentsCorrections	http://linkedlifedata.com/resource/pubmed/commentcorrection/1630904-1068447, http://linkedlifedata.com/resource/pubmed/commentcorrection/1630904-1651474, http://linkedlifedata.com/resource/pubmed/commentcorrection/1630904-2018503, http://linkedlifedata.com/resource/pubmed/commentcorrection/1630904-2173569, http://linkedlifedata.com/resource/pubmed/commentcorrection/1630904-2374710, http://linkedlifedata.com/resource/pubmed/commentcorrection/1630904-3822812, http://linkedlifedata.com/resource/pubmed/commentcorrection/1630904-4509343, http://linkedlifedata.com/resource/pubmed/commentcorrection/1630904-5069391, http://linkedlifedata.com/resource/pubmed/commentcorrection/1630904-5416936, http://linkedlifedata.com/resource/pubmed/commentcorrection/1630904-5888583, http://linkedlifedata.com/resource/pubmed/commentcorrection/1630904-6547529
pubmed:language	eng
pubmed:journal	http://linkedlifedata.com/resource/pubmed/journal/0411011
pubmed:citationSubset	IM
pubmed:chemical	http://linkedlifedata.com/resource/pubmed/chemical/Deoxyribonucleosides, http://linkedlifedata.com/resource/pubmed/chemical/Oligodeoxyribonucleotides
pubmed:status	MEDLINE
pubmed:month	Jul
pubmed:issn	0305-1048
pubmed:author	pubmed-author:AkagiMM, pubmed-author:OguraEE, pubmed-author:ShinoharaKK, pubmed-author:UedaYY, pubmed-author:UrataHH
pubmed:issnType	Print
pubmed:day	11
pubmed:volume	20
pubmed:owner	NLM
pubmed:authorsComplete	Y
pubmed:pagination	3325-32
pubmed:dateRevised	2009-11-18
pubmed:meshHeading	pubmed-meshheading:1630904-Chromatography, High Pressure Liquid, pubmed-meshheading:1630904-Deoxyribonucleosides, pubmed-meshheading:1630904-Nucleic Acid Conformation, pubmed-meshheading:1630904-Oligodeoxyribonucleotides
pubmed:year	1992
pubmed:articleTitle	Synthesis and properties of mirror-image DNA.
pubmed:affiliation	Osaka University of Pharmaceutical Sciences, Japan.
pubmed:publicationType	Journal Article, Research Support, Non-U.S. Gov't