Premium
Oxathiaphospholane Approach to the Synthesis of P‐Chiral, Isotopomeric Deoxy(ribonucleoside phosphorothioate)s and Phosphates Labeled with an Oxygen Isotope
Author(s) -
Guga Piotr,
Domański Krzysztof,
Stec Wojciech J.
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20010202)40:3<610::aid-anie610>3.0.co;2-w
Subject(s) - ribonucleoside , chemistry , nucleoside , oligonucleotide , stereochemistry , ribonucleotide , deoxyribonucleoside , tritium , nucleotide , rna , biochemistry , dna , physics , nuclear physics , gene
Diastereomerically pure and isotopically labeled 5′‐ O ‐DMT‐nucleoside‐3′‐ O ‐(2‐thio‐ and ‐oxo‐4,4‐“spiro”‐pentamethylene‐1,3,2‐[ 18 O]oxathiaphospholane)s were used for stereocontrolled synthesis of P‐chiral, isotopically labeled oligonucleotide phosphorothioates and phosphates, as well as “chimeric” PS 18 O/P 18 O 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