Inquiry Basket
5'-O-DMT-2'-fluoro-N2-isobutyryl-2'-Deoxy-guanosine 3'-CE phosphoramidite
5'-O-DMT-2'-Fluoro-N2-isobutyryl-2'-Deoxy-guanosine 3'-CE phosphoramidite is a modified phosphoramidite used in oligonucleotide synthesis. It features a 5'-dimethoxytrityl (DMT) protecting group at the 5'-hydroxyl position, a 2'-fluoro modification to enhance stability and binding affinity, an N2-isobutyryl group protecting the exocyclic amine of the guanine base, and a cyanoethyl (CE) group on the 3'-phosphoramidite. These modifications make it suitable for synthesizing oligonucleotides with improved resistance to enzymatic degradation and enhanced hybridization properties, which are crucial for applications in research, diagnostics, and therapeutics.
* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BRP-02173 | 5 g | $519 | In stock |
Catalog
BRP-02173
Synonyms
2'-Deoxy-5'-O-DMT-2'-fluoro-N2-isobutyrylguanosine 3'-CE phosphoramidite; 2'-F-iBu-G-CEP; 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-2'-fluoro-N-(2-methyl-1-oxopropyl)-Guanosine 3'-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite]; DMT-2'Fluoro-dG(iBu) Phosphoramidite; 2'-F-dG(iBu) 3'-CE phosphoramidite; DMT-2'-F-dG(iBu)-CE Phosphoramidite; 2'-F-dG(iBu)-CE Phosphoramidite; 2'-Fluoro-N2-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine-3'-CE-Phosphoramidite
CAS
144089-97-4
IUPAC Name
N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-3-fluorooxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
Molecular Weight
857.91
Molecular Formula
C44H53FN7O8P
Canonical SMILES
CC(C)C(=O)NC1=NC2=C(C(=O)N1)N=CN2C3C(C(C(O3)COC(C4=CC=CC=C4)(C5=CC=C(C=C5)OC)C6=CC=C(C=C6)OC)OP(N(C(C)C)C(C)C)OCCC#N)F
InChI
InChI=1S/C44H53FN7O8P/c1-27(2)40(53)49-43-48-39-37(41(54)50-43)47-26-51(39)42-36(45)38(60-61(58-24-12-23-46)52(28(3)4)29(5)6)35(59-42)25-57-44(30-13-10-9-11-14-30,31-15-19-33(55-7)20-16-31)32-17-21-34(56-8)22-18-32/h9-11,13-22,26-29,35-36,38,42H,12,24-25H2,1-8H3,(H2,48,49,50,53,54)/t35-,36-,38-,42-,61?/m1/s1
InChIKey
KJFUMXZZVYMQEU-AOCJBPQJSA-N
Purity
≥95%
Solubility
Soluble in DMSO
Appearance
White to Off-white Powder
Storage
Store at -20 °C
Chemical Structure:
Reference Reading
1. A universal, photocleavable DNA base: nitropiperonyl 2'-deoxyriboside
M C Pirrung, X Zhao, S V Harris. J Org Chem. 2001 Mar 23;66(6):2067-71. doi: 10.1021/jo001594r.
A universal, photochemically cleavable DNA base analogue would add desirable versatility to a number of methods in molecular biology. A novel C-nucleoside, nitropiperonyl deoxyriboside (NPdR, P), has been investigated for this purpose. NPdR can be converted to its 5'-DMTr-3'-CE-phosphoramidite and was incorporated into pentacosanucleotides by conventional synthesis techniques. The destabilizing effect on hybrid formation with a complementary strand when this P base opposes A, T, and G was found to be 3-5 kcal/mol, but 9 kcal/mol when it opposes C. Brief irradiation (lambda > 360 nm, 20 min) of DNA containing the P base and piperidine treatment causes strand cleavage giving the 3'- and 5'-phosphates. Two significant recent interests, universal/non-hydrogen-bonding base analogues and photochemical backbone cleavage, have thus been combined in a single molecule that serves as a light-based DNA scissors.
