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Stereo-Reproducibility of the Phosphoramidite Method in the Synthesis of Oligonucleotide Phosphorothioates

✍ Scribed by T.K. Wyrzykiewicz; D.L. Cole

Publisher: Elsevier Science
Year: 1995
Tongue: English
Weight: 503 KB
Volume: 23
Category: Article
ISSN: 0045-2068
DOI: 10.1006/bioo.1995.1003

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✦ Synopsis

Stereo-reproducibility of phosphoroamidite-based phosphorothioate oligonucleotide synthesis is examined through synthesis of singly thioate-substituted oligodeoxynucleotide model compounds. Baseline RP-HPLC resolution of resulting Rp and Sp diastereomers allowed accurate determination of any enantiomeric excess at each phosphorothioate linkage. Our results show that phosphorothioate linkage formation is not a stereo-random process. All investigated stereoisomeric phosphorothioate diester linkages were formed with a small, reproducible excess of the (\mathrm{R}) isomer ( (2-6 %) per linkage). Regardless of the synthesized sequence, all (\mathrm{Rp} / \mathrm{Sp}) diastereoisomer ratios were between (50: 50) and (60: 40), indicating that this synthesis process is under inherent stereochemical control. O 1995 Academic Press. Inc.

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