5'-O-DMT-2'-O-tert-Butyldimethylsilyl-N6-methyl-adenosine 3'-CE phosphoramidite - CAS 588698-79-7

Catalog number: BRA-037

5'-O-DMT-2'-O-tert-Butyldimethylsilyl-N6-methyl-adenosine 3'-CE phosphoramidite is a vital compound used in the biomedical industry for synthesizing RNA molecules. This phosphoramidite aids in the incorporation of modified adenosine bases during RNA synthesis, enabling researchers to study specific drug targets or diseases related to N6-methyladenosine methylation. By providing precise adenosine modifications, this product facilitates the investigation of gene expression and regulatory mechanisms, leading to potential breakthroughs in drug discovery and disease understanding.

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Synonyms

Adenosine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-[(1,1-dimethylethyl)dimethylsilyl]-N-methyl-, 3'-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite]; N6-Me-rA phosphoramidite; 5'-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-3'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-2'-O-[dimethyl(2-methyl-2-propanyl)silyl]-N-methyladenosine

CAS

588698-79-7

IUPAC Name

3-[[(2R,3R,4R,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[tert-butyl(dimethyl)silyl]oxy-5-[6-(methylamino)purin-9-yl]oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile

Molecular Weight

898.11

Molecular Formula

C47H64N7O7PSi

Canonical SMILES

CC(C)N(C(C)C)P(OCCC#N)OC1C(OC(C1O[Si](C)(C)C(C)(C)C)N2C=NC3=C(N=CN=C32)NC)COC(C4=CC=CC=C4)(C5=CC=C(C=C5)OC)C6=CC=C(C=C6)OC

InChI

InChI=1S/C47H64N7O7PSi/c1-32(2)54(33(3)4)62(58-28-16-27-48)60-41-39(59-45(42(41)61-63(11,12)46(5,6)7)53-31-52-40-43(49-8)50-30-51-44(40)53)29-57-47(34-17-14-13-15-18-34,35-19-23-37(55-9)24-20-35)36-21-25-38(56-10)26-22-36/h13-15,17-26,30-33,39,41-42,45H,16,28-29H2,1-12H3,(H,49,50,51)/t39-,41-,42-,45-,62?/m1/s1

InChIKey

GPLFLRPEMRRWIR-UTZPQXNGSA-N

Boiling Point

859.0±75.0°C (Predicted)

Purity

≥98% by HPLC

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.