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ALD00602

Sigma-Aldrich

(–)-PSI Reagent

95%

Synonym(s):

(2S,3aS,6R,7aS)-3a-Methyl-2-((perfluorophenyl)thio)-6-(prop-1-en-2-yl)hexahydrobenzo[d][1,3,2]oxathiaphosphole 2-sulfide, (–)-Ψ, Phosphorus-Sulfur Incorporation Reagent

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About This Item

Empirical Formula (Hill Notation):
C16H16F5OPS3
CAS Number:
2245335-70-8
Molecular Weight:
446.46
UNSPSC Code:
12352101
NACRES:
NA.22

Assay

95%

form

powder or crystals

mp

103-107 °C

Application

Air- and moisture-tolerant, this (-)-PSI Reagent was developed in the Baran lab for stereocontrolled synthesis of phosphorothioate oligonucleotides. The enantiomer, (+)-PSI Reagent, is also available (cat# ALD00604).
The PSI Reagents open access to thiophosphate-based nucleotide molecules with therapeutic promise as demonstrated by the Baran lab in the preparation of pure stereoisomers of cyclic dinucleotides (CDNs) and antisense oligonucleotides (ASOs).

Learn more about PI and PSI reagents

Other Notes

Unlocking P(V): Reagents for chiral phosphorothioate synthesis

PSI on OpenFlask

Legal Information

PCT/US2019/027256; U.S. Nonprovisional Patent Application #16/382,692

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ALD00618

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW0630
MKCT5558
MKCK2384
MKCM3402
MKCL7375

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Kyle W Knouse et al.
Science (New York, N.Y.), 361(6408), 1234-1238 (2018-08-04)
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

Articles

PI and PSI – Chiral phosphorus incorporation harnessing the potential of P(V)

PI and PSI reagents are a platform of phosphate-based reagents for phosphorylation and phosphothiolation of nucleotides and peptides developed by the Baran lab.

PI and PSI – Chiral phosphorus incorporation harnessing the potential of P(V)

PI and PSI reagents are a platform of phosphate-based reagents for phosphorylation and phosphothiolation of nucleotides and peptides developed by the Baran lab.

PI and PSI – Chiral phosphorus incorporation harnessing the potential of P(V)

PI and PSI reagents are a platform of phosphate-based reagents for phosphorylation and phosphothiolation of nucleotides and peptides developed by the Baran lab.

PI and PSI – Chiral phosphorus incorporation harnessing the potential of P(V)

PI and PSI reagents are a platform of phosphate-based reagents for phosphorylation and phosphothiolation of nucleotides and peptides developed by the Baran lab.

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