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5'-O-DMT-2'-O-TBDMS-N2-isobutyryl-L-Guanosine 3'-CE phosphoramidite
5'-O-DMT-2'-O-TBDMS-N2-isobutyryl-L-Guanosine 3'-CE phosphoramidite, a sophisticated compound integral to the production of custom oligonucleotides, showcases remarkable versatility. It serves as a phosphoramidite foundation during solid-phase DNA synthesis, facilitating the integration of guanosine modifications. By harnessing this product, nucleic acid researchers can probe gene expression or delve into the impact of guanosine alterations on ailments such as cancer.
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Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BRP-02186 | 1 g | $990 | In stock |
Catalog
BRP-02186
Synonyms
DMT-2'-O-TBDMS-L-rG(ibu) Phosphoramidite; N-[9-[5-O-[Bis(4-methoxyphenyl)phenylmethyl]-3-O-[[bis(1-methylethyl)amino](2-cyanoethoxy)phosphino]-2-O-[(1,1-dimethylethyl)dimethylsilyl]-β-L-ribofuranosyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]-2-methylpropanamide; L-rG(ibu) Phosphoramidite; 5'-O-DMTr-2'-O-TBDMS-L-G(iBu)-3'-CE-Phosphoramidite; N2-Isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(t-butyl-dimethylsilyl)-L-guanosine-3'-cyanoethyl Phosphoramidite
CAS
679809-76-8
IUPAC Name
N-[9-[(2S,3S,4S,5S)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-[tert-butyl(dimethyl)silyl]oxy-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
Molecular Weight
970.19
Molecular Formula
C50H68N7O9PSi
Canonical SMILES
N#CCCOP(OC1C(OC(N2C=NC=3C(=O)N=C(NC(=O)C(C)C)NC32)C1O[Si](C)(C)C(C)(C)C)COC(C=4C=CC=CC4)(C5=CC=C(OC)C=C5)C6=CC=C(OC)C=C6)N(C(C)C)C(C)C
InChI
InChI=1S/C50H68N7O9PSi/c1-32(2)45(58)54-48-53-44-41(46(59)55-48)52-31-56(44)47-43(66-68(12,13)49(7,8)9)42(65-67(63-29-17-28-51)57(33(3)4)34(5)6)40(64-47)30-62-50(35-18-15-14-16-19-35,36-20-24-38(60-10)25-21-36)37-22-26-39(61-11)27-23-37/h14-16,18-27,31-34,40,42-43,47H,17,29-30H2,1-13H3,(H2,53,54,55,58,59)/t40-,42-,43-,47-,67?/m0/s1
InChIKey
PGJKESPHANLWME-ZEXYNXKFSA-N
Purity
≥98% by HPLC
Appearance
White, off-white to faint yellow powder
Storage
Store at -20 °C
Related CAS
147201-04-5 (R-isomer)
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.
