| 5'-Aldehyde-Modifier C2 Phosphoramidite |
ALDEHYDE MODIFICATION
Aldehyde modifiers would be attractive electrophilic substitutions in oligonucleotides since they are able to react with amino groups to form a Schiff’s base, with hydrazino groups to form hydrazones, and with semicarbazides to form semi-carbazones. The Schiff’s base is unstable and must be reduced with sodium borohydride to form a stable linkage but hydrazones and semicarbazides are very stable linkages.
Our collaboration with Epoch Biosciences, a subsidiary of Nanogen, Inc., has allowed us to offer 5'-Aldehyde-Modifier C2 Phosphoramidite. The acetal protecting group is sufficiently hydrophobic for use in RP HPLC and cartridge purification and is readily removed after oligonucleotide synthesis under standard oligonucleotide detritylation conditions with 80% acetic acid / 20% water or 2% aqueous trifluoroacetic acid during cartridge purification.
A formylindole nucleoside analogue has been used to introduce aldehyde groups within an oligonucleotide or at the 5’ terminus. This product has no protecting group on the aldehyde, which means that deprotection of the modified oligonucleotide can be done without changing preferred conditions.
Catalog Number: 10-1933-xx
Description: 5'-Aldehyde-Modifier C2 Phosphoramidite
2-[4-(5,5-Diethyl-1,3-dioxan-2-yl)phenoxy]ethan-1-yl-
[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite |
| Formula: C25H41N2O5P |
M.W.: 480.58 |
F.W.: 228.14 |
Diluent: Anhydrous Acetonitrile |
| Coupling: No changes needed from standard method recommended by synthesizer manufacturer. |
| Deprotection: See Technical Bulletin for details (www.glenresearch.com/Technical/TB_Aldehyde_Modifier.pdf). Technical Bulletin |
| Storage: Freezer Storage, -10 to -30°C, dry |
| Stability in Solution: 2-3 days |
| Please Note: This Product is for research purposes only, and may not be used for commercial, clinical, diagnostic or any other use. The Product is subject to proprietary rights of Epoch Biosciences, Inc. and is made and sold under license from Epoch Biosciences, Inc. There is no implied license for commercial use with respect to this Product and a license must be obtained directly from Epoch Biosciences, Inc. with respect to any proposed commercial use of this Product. "Commercial use" includes but is not limited to the sale, lease, license or other transfer of the Product or any material derived or produced from it, the sale, lease, license or other grant of rights to use the Product or any material derived or produced from it, or the use of the Product to perform services for a fee for third parties (including contract research). Eclipse, Gig Harbor Green, Redmond Red and Yakima Yellow are trademarks of Epoch Biosciences, Inc. |
ALDEHYDE MODIFICATION
Aldehyde modifiers would be attractive electrophilic substitutions in oligonucleotides since they are able to react with amino groups to form a Schiff’s base, with hydrazino groups to form hydrazones, and with semicarbazides to form semi-carbazones. The Schiff’s base is unstable and must be reduced with sodium borohydride to form a stable linkage but hydrazones and semicarbazides are very stable linkages.
Our collaboration with Epoch Biosciences, a subsidiary of Nanogen, Inc., has allowed us to offer 5'-Aldehyde-Modifier C2 Phosphoramidite. The acetal protecting group is sufficiently hydrophobic for use in RP HPLC and cartridge purification and is readily removed after oligonucleotide synthesis under standard oligonucleotide detritylation conditions with 80% acetic acid / 20% water or 2% aqueous trifluoroacetic acid during cartridge purification.
A formylindole nucleoside analogue has been used to introduce aldehyde groups within an oligonucleotide or at the 5’ terminus. This product has no protecting group on the aldehyde, which means that deprotection of the modified oligonucleotide can be done without changing preferred conditions.
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