Oxathiaphospholane Approach to the Synthesis of P-Chiral, Isotopomeric Deoxy(ribonucleoside phosphorothioate)s and Phosphates Labeled with an Oxygen Isotope

Diastereomerically pure and isotopically labeled 5′‐O‐DMT‐nucleoside‐3′‐O‐(2‐thio‐ and ‐oxo‐4,4‐“spiro”‐pentamethylene‐1,3,2‐[18O]oxathiaphospholane)s were used for stereocontrolled synthesis of P‐chiral, isotopically labeled oligonucleotide phosphorothioates and phosphates, as well as “chimeric” PS...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2001-02, Vol.40 (3), p.610-613
Main Authors: Guga, Piotr, Domański, Krzysztof, Stec, Wojciech J.
Format: Article
Language:English
Subjects:
isotopic labeling
oligonucleotides
phosphorothioates
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Summary:Diastereomerically pure and isotopically labeled 5′‐O‐DMT‐nucleoside‐3′‐O‐(2‐thio‐ and ‐oxo‐4,4‐“spiro”‐pentamethylene‐1,3,2‐[18O]oxathiaphospholane)s were used for stereocontrolled synthesis of P‐chiral, isotopically labeled oligonucleotide phosphorothioates and phosphates, as well as “chimeric” PS18O/P18O oligomers (see scheme) without loss of isotope enrichment. DBU=1,8‐diazabicyclo[5.4.0]undec‐7‐ene, DMT=4,4′‐dimethoxytrityl, ROH=3′‐O‐acetylthymidine, Bz=benzoyl
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20010202)40:3<610::AID-ANIE610>3.0.CO;2-W