Inquiry Basket
5'-O-DMT-2'-O-Propargyl-N2-isobutyryl-Guanosine 3'-CE phosphoramidite
2'-O-Propargyl G(iBu)-3'-phosphoramidite is a vital compound extensively used in the field of biomedicine. This compound acting as a versatile building block for the synthesis of modified nucleosides and oligonucleotides. It finding applications in the development of therapeutic compounds, particularly for the reserch of viral infections and genetic diseases.
* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.
Catalog
BRP-00321
Synonyms
2'-O-Propynyl-ibu-rG phosphoramidite; N2-iBu-5'-O-DMTr-2'-O-propargylguanosine-3'-CED-phosphoramidite; N2-iso-Butyroyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-propargyl guanosine-3'-O-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite; 5'-O-DMT-N2-isobutyryl-2'-O-propynylguanosine 3'-CE phosphoramidite; 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-N-(2-methyl-1-oxopropyl)-2'-O-2-propynyl-guanosine 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite]; 5'-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-3'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-N-isobutyryl-2'-O-2-propyn-1-ylguanosine; DMTr-2'-O-propargyl-rG(iBu)-3'-CE-Phosphoramidite; 2'-O-Propargyl G(iBu)-3'-phosphoramidite; N2-iBu-DMT-2'-O-propargyl-G-CE-Phosphoramidite; 2'-O-propargyl Guanosine (n-ibu) CED phosphoramidite
CAS
171486-61-6
IUPAC Name
N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-3-prop-2-ynoxyoxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
Molecular Weight
893.96
Molecular Formula
C47H56N7O9P
Canonical SMILES
CC(C)C(=O)NC1=NC2=C(C(=O)N1)N=CN2C3C(C(C(O3)COC(C4=CC=CC=C4)(C5=CC=C(C=C5)OC)C6=CC=C(C=C6)OC)OP(N(C(C)C)C(C)C)OCCC#N)OCC#C
InChI
InChI=1S/C47H56N7O9P/c1-10-26-59-41-40(63-64(61-27-14-25-48)54(31(4)5)32(6)7)38(62-45(41)53-29-49-39-42(53)50-46(52-44(39)56)51-43(55)30(2)3)28-60-47(33-15-12-11-13-16-33,34-17-21-36(57-8)22-18-34)35-19-23-37(58-9)24-20-35/h1,11-13,15-24,29-32,38,40-41,45H,14,26-28H2,2-9H3,(H2,50,51,52,55,56)/t38-,40-,41-,45-,64?/m1/s1
InChIKey
AGWGPRXHCUPJJO-VCGWOZLGSA-N
Purity
≥98% by HPLC
Appearance
White, off-white to faint yellow powder
Storage
Store at -20 °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.
