N4-Benzoyl-5'-O-DMT-2'-O-MOE-cytidine 3'-CE phosphoramidite - CAS 251647-54-8

Catalog number: BRP-02191

N4-Benzoyl-5'-O-DMT-2'-O-MOE-cytidine 3'-CE phosphoramidite

N4-Benzoyl-5'-O-DMT-2'-O-MOE-cytidine 3'-CE phosphoramidite is a modified phosphoramidite designed for efficient and controlled synthesis of RNA and DNA oligonucleotides. The protective groups and modifications, such as N4-benzoyl, 5'-O-DMTr, and 2'-O-MOE, enhance the stability of the resulting nucleic acids and facilitate their incorporation into nucleic acid chains during solid-phase synthesis. This compound is crucial in the production of antisense oligonucleotides, siRNA, probes, and primers, providing enhanced resistance to enzymatic degradation and improved performance in various applications.

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.
Catalog
BRP-02191
Synonyms
N4-Bz-5'-O-DMTr-2'-O-(2-methoxyethyl)cytidine-3'-CED-phosphoramidite; 2'-O-MOE-C(Bz)-3'-phosphoramidite; N4-Acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-cytidine-3'-CE-cyanoethyl Phosphoramidite; N-Benzoyl-5'-O-[bis(4-methoxyphenyl)(phenyl)methyl]-3'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-2'-O-(2-methoxyethyl)cytidine; Cytidine, N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-(2-methoxyethyl)-, 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite]; 2'-O-MOE-rC(Bz) Phosphoramidite
CAS
251647-54-8
IUPAC Name
N-[1-[(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]-2-oxopyrimidin-4-yl]benzamide
Molecular Weight
907.99
Molecular Formula
C49H58N5O10P
Canonical SMILES
CC(C)N(C(C)C)P(OCCC#N)OC1C(OC(C1OCCOC)N2C=CC(=NC2=O)NC(=O)C3=CC=CC=C3)COC(C4=CC=CC=C4)(C5=CC=C(C=C5)OC)C6=CC=C(C=C6)OC
InChI
InChI=1S/C49H58N5O10P/c1-34(2)54(35(3)4)65(62-30-14-28-50)64-44-42(63-47(45(44)60-32-31-57-5)53-29-27-43(52-48(53)56)51-46(55)36-15-10-8-11-16-36)33-61-49(37-17-12-9-13-18-37,38-19-23-40(58-6)24-20-38)39-21-25-41(59-7)26-22-39/h8-13,15-27,29,34-35,42,44-45,47H,14,30-33H2,1-7H3,(H,51,52,55,56)/t42-,44-,45-,47-,65?/m1/s1
InChIKey
IAFVTVZPQIFRAU-NXPFYNPLSA-N
Purity
≥95%
Appearance
White Powder
Storage
Store at -20 °C

QC Data

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.
Related Products
Online Inquiry
Verification code
0
Inquiry Basket

No data available, please add!

Delete selectedGo to checkout

We use cookies to understand how you use our site and to improve the overall user experience. This includes personalizing content and advertising. Read our Privacy Policy

Accept Cookies
x