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BA 0352
Product Information Molecular Structure

8-Styryl-dG CEP

Notes: Photochromic nucleoside (PCN) that provides reversible duplex regulation via a light induced trans-cis isomerization.

Description: Ogasawara and co-workers have reported the use of 8-substituted dG derivatives that provide reversible duplex regulation via a light induced trans-cis isomerization.1,2 The trans isomer of 8-styryl-2-deoxyguanosine (8STG) is one such photochromic nucleoside (PCN). When a 12-bp duplex containing 8STG is irradiated for 5 minutes at 370 nm, the double bond isomerizes to the cis geometry with 86% conversion. Subsequent irradiation for 2 minutes at 254 nm returns the double bond to the trans geometry with 94% conversion. Both trans and cis isomers are thermally stable but readily interconvert at room temperature upon irradiation with light of the appropriate wavelength. The Tm value of the duplex containing a trans -PCN is 7.9oC higher than the Tm value of the same duplex containing a cis-PCN. When three 8STG insertions are inserted into a 20-bp duplex, the trans -PCNs permit duplex formation whereas the cis-PCNs cause denaturation of the duplex. This phenomenon is evidenced by changes in the circular dichroism spectra before and after irradiation of the duplex containing trans -PCNs at 370 nm. Conversely, when the single strands containg cis-PCNs are irradiated at 254 nm hybridization occurs as the trans isomer is formed.

Berry & Associates now offers 8-Styryl-dG CEP (BA 0352) for the in automated synthesis of PCN-containing oligonucleotides. For more information, download a Product Information Sheet for BA 0352 here.

Substitution of other aromatic moieties for the phenyl ring provides PCNs that operate at different wavelengths. For example with 8-(2-napthalen-2-yl)vinly-2-deoxyguanosine (8NVG) the trans to cisconversion occurs with 410 nm irradiation and reverts at 290 nm and with 8-(2-fluoren-2-yl)vinyl-2-deoxyguanosine (8FVG) ) the trans to cisconversion occurs with 420 nm irradiation and reverts at 310 nm. 8STG, 8NVG, and 8FVG all have the common synthetic precursor 8-vinyl-dG. Thus we now also offer PR 3335. as a versatile synthetic intermediate for the preparation of these and other PCNs.

1. Ogasawara, S.; Saito, I.; Maeda, M. Tetr. Lett., 2008, 49, 2479-82.

2. Ogasawara, S.; Maeda, M. Angew. Chem. Int. Ed., 2008, 47, 8839-42.

8-Styryl-dG CEP
Product Details Product Pricing

MF: C51H59N8O7P

MW: 927.04

CAS NO: 1101864-12-3

Storage Conditions: -20 C

Purity≥90%

Availability: 

Stock maintained. Ships within 1-3 days.

Alternate Name: 

8-[(1E)-2-Phenylethenyl]-dG CEP

Alternate Name: 

8STG
Unit Weight Unit Price Quantity
100 µmol $752.00
0.25 g $1,560.00
 
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