5′-O-DMT-N2-isobutyryl-2′-O-methoxyethylguanosine 3′-CE phosphoramidite is used to incorporate 2′-O-methoxyethyl-modified G into oligonucleotides, which is useful for antisense RNA.
Synonyms
5′-O-DMTr-N2-iBu-2′-O-MOE-guanosine-3′-CED phosphoramidite; 5′-O-(4,4′-Dimethoxytrityl)-N2-iso-butyroyl-2′-O-(2-methoxyethyl)guanosine-3′-O-[(2-cyanoethyl)(N,N-diisopropyl)]phosphoramidite; 2′-MOE-G(iBu)-3′-phosphoramidite; DMT-2M-O-Me-rG(ib) amidite; N2-isobutyryl-5′-O-DMT-2′-O-(2-methoxyethyl)guanosine 3′-CE phosphoramidite; N-Isobutyryl-2′-O-(2-methoxyethyl)-3′-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5′-O-(4,4′-dimethoxytrityl)guanosine; 5′-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-3′-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-N-isobutyryl-2′-O-(2-methoxyethyl)guanosine
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-(2-methoxyethoxy)oxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
Molecular Formula
C47H60N7O10P
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)OCCOC
InChI
InChI=1S/C47H60N7O10P/c1-30(2)43(55)51-46-50-42-39(44(56)52-46)49-29-53(42)45-41(60-27-26-57-7)40(64-65(62-25-13-24-48)54(31(3)4)32(5)6)38(63-45)28-61-47(33-14-11-10-12-15-33,34-16-20-36(58-8)21-17-34)35-18-22-37(59-9)23-19-35/h10-12,14-23,29-32,38,40-41,45H,13,25-28H2,1-9H3,(H2,50,51,52,55,56)/t38-,40-,41-,45-,65?/m1/s1
InChIKey
LADCDGNEBIQAAU-SBCRAQIVSA-N
Appearance
White to Off-white Solid
Description
5′-O-DMT-N2-isobutyryl-2′-O-methoxyethylguanosine 3′-CE phosphoramidite is used to incorporate 2′-O-methoxyethyl-modified G into oligonucleotides, which is useful for antisense RNA.
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.
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