5'-O-DMT-2'-O-TBDMS-5-Methy-L-Uridine 3'-CE phosphoramidite - CAS 159639-78-8

Catalog number: BRA-023

5'-O-DMT-2'-O-TBDMS-5-Methyl-L-Uridine 3'-CE phosphoramidite is a DNA synthesis building block with a 5'-dimethoxy trityl group.

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Synonyms

Uridine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-[(1,1-dimethylethyl)dimethylsilyl]-5-methyl-, 3'-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite]; 5-Methyl-5'-O-(4,4'-Dimethoxytrityl)-2'-O-(t-butyldimethylsilyl)-uridine-3'-cyanoethyl phosphoramidite; 5-O-(4,4'-dimethoxytrityl)-3-O-(diisopropylamino-2-cyanoethoxyphosphanyl)-2-O-(tert-butyl-dimethyl-silyl)-1-deoxy-1-thymin-1-yl-beta-D-ribo-pentofuranose; 5'-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-3'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-2'-O-[dimethyl(2-methyl-2-propanyl)silyl]-5-methyluridine; DMT-2'-O-TBDMS-5-Me-rU Phosphoramidite

CAS

159639-78-8

IUPAC Name

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

Molecular Weight

875.09

Molecular Formula

C46H63N4O9PSi

Canonical SMILES

CC1=CN(C(=O)NC1=O)C2C(C(C(O2)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)OP(N(C(C)C)C(C)C)OCCC#N)O[Si](C)(C)C(C)(C)C

InChI

InChI=1S/C46H63N4O9PSi/c1-31(2)50(32(3)4)60(56-28-16-27-47)58-40-39(57-43(41(40)59-61(11,12)45(6,7)8)49-29-33(5)42(51)48-44(49)52)30-55-46(34-17-14-13-15-18-34,35-19-23-37(53-9)24-20-35)36-21-25-38(54-10)26-22-36/h13-15,17-26,29,31-32,39-41,43H,16,28,30H2,1-12H3,(H,48,51,52)/t39-,40-,41-,43-,60?/m1/s1

InChIKey

KYRSLFQMFXXGLW-IEXCOMMKSA-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.