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Merck

Unlocking P(V): Reagents for chiral phosphorothioate synthesis.

Science (New York, N.Y.) (2018-08-04)
Kyle W Knouse, Justine N deGruyter, Michael A Schmidt, Bin Zheng, Julien C Vantourout, Cian Kingston, Stephen E Mercer, Ivar M Mcdonald, Richard E Olson, Ye Zhu, Chao Hang, Jason Zhu, Changxia Yuan, Qinggang Wang, Peter Park, Martin D Eastgate, Phil S Baran
초록

Phosphorothioate nucleotides have emerged as powerful pharmacological substitutes of their native phosphodiester analogs with important translational applications in antisense oligonucleotide (ASO) therapeutics and cyclic dinucleotide (CDN) synthesis. Stereocontrolled installation of this chiral motif has long been hampered by the systemic use of phosphorus(III) [P(III)]-based reagent systems as the sole practical means of oligonucleotide assembly. A fundamentally different approach is described herein: the invention of a P(V)-based reagent platform for programmable, traceless, diastereoselective phosphorus-sulfur incorporation. The power of this reagent system is demonstrated through the robust and stereocontrolled synthesis of various nucleotidic architectures, including ASOs and CDNs, via an efficient, inexpensive, and operationally simple protocol.

MATERIALS
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브랜드
제품 설명

Sigma-Aldrich
PSIO
Sigma-Aldrich
(–)-PSI Reagent, 95%
Sigma-Aldrich
(+)-PSI Reagent, 95%