Skip to Content
MilliporeSigma
All Photos(4)

Key Documents

View All Documentation

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

Sign Into View Organizational & Contract Pricing

Select a Size

500 MG
$159.00
5 G
$921.00
25 G
$1,852.50
100 G
$4,900.00

$159.00

List Price$212.00Save 25%

Estimated to ship onMarch 07, 2025

Request a Bulk Order
All Photos(4)

Select a Size

Change View
500 MG
$159.00
5 G
$921.00
25 G
$1,852.50
100 G
$4,900.00

About This Item

Empirical Formula (Hill Notation):
C16H16F5OPS3
CAS Number:
2245335-70-8
Molecular Weight:
446.46
MDL number:
MFCD32068365
UNSPSC Code:
12352101
NACRES:
NA.22

$159.00

List Price$212.00Save 25%

Estimated to ship onMarch 07, 2025

Request a Bulk Order

assay

95%

form

powder or crystals

mp

103-107 °C

SMILES string

Fc1c(c(c(c(c1F)F)S[P]2(=S)S[C@@]3([C@@H](O2)C[C@@H](CC3)C(=C)C)C)F)F

InChI

1S/C16H16F5OPS3/c1-7(2)8-4-5-16(3)9(6-8)22-23(24,26-16)25-15-13(20)11(18)10(17)12(19)14(15)21/h8-9H,1,4-6H2,2-3H3/t8-,9+,16+,23?/m1/s1

InChI key

YPYCUYPOHPPYAS-QSHUGKRNSA-N

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

Related product

Product No.
Description
Pricing

88185

Tetrazole solution, suitable for DNA synthesis, filtered through a 1 μm filter, ~0.45 M in acetonitrile

302309

2-Cyanoethyl N,N-diisopropylchlorophosphoramidite, Cl 13.5-15.5 %

416436

Dibenzyl N,N-diisopropylphosphoramidite, technical grade, 90%

392561

Methyl N,N,N′,N′-tetraisopropylphosphorodiamidite, 97%

305995

2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphorodiamidite, 97%

419362

Di-tert-butyl N,N-diisopropylphosphoramidite, 95%

760838

Allyl tetraisopropylphosphorodiamidite, 95%

760811

Bis[2-(trimethylsilyl)ethyl] N,N-diisopropylphosphoramidite, 96%

766305

Bis(2-cyanoethyl)-N,N-diisopropylphosphoramidite, 95%

ALD00604

(+)-PSI Reagent, 95%

ALD00613

PSI2

ALD00617

(−)-PI Reagent, ≥95%

ALD00618

(+)-PI Reagent, ≥95%

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCW0630
MKCT5558
MKCK2384
MKCM3402
MKCL7375

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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.

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service