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N4-Benzoyl-2'-O-tert-butyldimethylsilyl-5'-O-DMT-cytidine 3'-CE phosphoramidite
N4-Benzoyl-2'-O-tert-butyldimethylsilyl-5'-O-DMT-cytidine 3'-CE phosphoramidite is an indispensable biomolecule, finding profound applications within the intricate synthesis of bespoke nucleotides, thus aiding in genetic investigations.
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Catalog
BRP-02162
Synonyms
Bz-rC Phosphoramidite; N-Bz-2'-O-TBDMS-5'-DMT-cytidine 3'-CE phosphoramidite; Cytidine, N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-[(1,1-dimethylethyl)dimethylsilyl]-, 3'-[2-cyanoethylbis(1-methylethyl)phosphoramidite]; N4-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-tert-butyldimethylsilyl)cytidine 3'-O-[O-(2-cyanoethyl)-N,N'-diisopropylphosphoramidite]; 5'-DMT-2'-TBDMS-N4-Bz-rC phosphoramidite; 5'-O-DMT-2'-O-TBDMS-rC (Bz) phosphoramidite; 5'-O-DMT-2'-O-TBDMS-rC(Bz) 3'-CE phosphoramidite
CAS
118380-84-0
IUPAC Name
N-[1-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-[tert-butyl(dimethyl)silyl]oxy-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
Molecular Weight
964.19
Molecular Formula
C52H66N5O9PSi
Canonical SMILES
CC(C)N(C(C)C)P(OCCC#N)OC1C(OC(C1O[Si](C)(C)C(C)(C)C)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/C52H66N5O9PSi/c1-36(2)57(37(3)4)67(63-34-18-32-53)65-46-44(35-62-52(39-21-16-13-17-22-39,40-23-27-42(60-8)28-24-40)41-25-29-43(61-9)30-26-41)64-49(47(46)66-68(10,11)51(5,6)7)56-33-31-45(55-50(56)59)54-48(58)38-19-14-12-15-20-38/h12-17,19-31,33,36-37,44,46-47,49H,18,34-35H2,1-11H3,(H,54,55,58,59)/t44-,46-,47-,49-,67?/m1/s1
InChIKey
VWNXEDLLHIFAOL-YOVDOAOFSA-N
Appearance
White to off-white solid
Storage
Store at 2-8 °C
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.
