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Nucleosides Nucleotides Nucleic Acids. 2011 Sep;30(9):706-25. doi: 10.1080/15257770.2011.597366.

Sulfurization of dinucleoside phosphite triesters with chiral disulfides.

Author information

1
Department of Chemistry and Biochemistry, Queens College and the Graduate Center of the City University of New York, Flushing, New York, USA.

Abstract

Sixteen chiral analogues of phenylacetyl disulfide (PADS) and 5-methyl-3H-1,2,4-dithiazol-3-one (MEDITH) were used to sulfurize five dithymidine phosphite triesters, each incorporating a β-cyanoethoxy or siloxy group. Each mixture of S(P):R(P) phosphite triester diastereomers was combined with approximately one fourth of an equivalent of each of the sulfurizing reagents, and the R(PS):S(PS) diastereomer ratios of the resulting phosphite sulfides or phosphorothioates were determined by reverse-phase HPLC. Diastereoselectivities and corresponding diastereomeric excess (de) values were calculated by correcting for the starting triester diastereomer ratios. The highest de values for R(PS) and S(PS) phosphorothioates were 14.7% and 7.9%, respectively, both using MEDITH analogues.

PMID:
21902473
DOI:
10.1080/15257770.2011.597366
[Indexed for MEDLINE]

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