5'-O-DMT-2'-O-TBDMS-L-Uridine 3'-CE phosphoramidite - CAS 144490-31-3

Catalog number: BRA-016

5'-O-DMT-2'-O-TBDMS-L-Uridine 3'-CE phosphoramidite, a highly versatile and indispensable compound within the biomedical industry, occupies a paramount position in the synthesis of oligonucleotides of immense significance. Blending seamlessly with various applications including gene therapy, nucleic acid-based diagnostics, and drug development, this invaluable marvel propels the progress of medical science. Its inherent ability to modify nucleotide sequences bestows unmatched stability and facilitates target-specific drug conveyance, fostering advancements in the treatment of multifarious diseases, encompassing cancer and genetic disorders.

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Ordering Information

Catalog Number	Size	Price	Stock	Quantity
BRA-016	1 g	$990	In stock

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Synonyms

2,4(1H,3H)-Pyrimidinedione, 1-[5-O-[bis(4-methoxyphenyl)phenylmethyl]-3-O-[[bis(1-methylethyl)amino](2-cyanoethoxy)phosphino]-2-O-[(1,1-dimethylethyl)dimethylsilyl]-β-L-ribofuranosyl]-; 1-[2-O-(tert-Butyldimethylsilyl)-3-O-[diisopropylamino(2-cyanoethoxy)phosphino]-5-O-(4,4'-dimethoxytrityl)-beta-L-ribofuranosyl]uracil; DMT-2'-O-TBDMS-L-rU Phosphoramidite

CAS

144490-31-3

IUPAC Name

3-[[(2S,3S,4S,5S)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[tert-butyl(dimethyl)silyl]oxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile

Molecular Weight

861.06

Molecular Formula

C45H61N4O9PSi

Canonical SMILES

CC(C)N(C(C)C)P(OCCC#N)OC1C(OC(C1O[Si](C)(C)C(C)(C)C)N2C=CC(=O)NC2=O)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC

InChI

InChI=1S/C45H61N4O9PSi/c1-31(2)49(32(3)4)59(55-29-15-27-46)57-40-38(56-42(48-28-26-39(50)47-43(48)51)41(40)58-60(10,11)44(5,6)7)30-54-45(33-16-13-12-14-17-33,34-18-22-36(52-8)23-19-34)35-20-24-37(53-9)25-21-35/h12-14,16-26,28,31-32,38,40-42H,15,29-30H2,1-11H3,(H,47,50,51)/t38-,40-,41-,42-,59?/m0/s1

InChIKey

SKNLXHRBXYGJOC-BKOBKXGTSA-N

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.