5'-O-DMT-2'-O-tert-Butyldimethylsilyl-N2-isobutyrylguanosine 3'-CE phosphoramidite - CAS 147201-04-5

Catalog number: BRA-019

5'-O-DMT-2'-O-tert-Butyldimethylsilyl-N2-isobutyrylguanosine 3'-CE phosphoramidite is a classic protected 2-OTBDMS phosphoramidite used for incorporating ribo-G into synthetic oligonucleotides.

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Synonyms

5'-O-(4,4-Dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]-N-isobutyrylguanosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite; ibu-rG CE phosphoramidite; DMT-2'-O-TBDMS-rG(ib) Phosphoramidite; I-bu-rG Phosphoramidite; 5'-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-3'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-2'-O-[dimethyl(2-methyl-2-propanyl)silyl]-N-isobutyrylguanosine

CAS

147201-04-5

IUPAC Name

N-[9-[(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]-6-oxo-1H-purin-2-yl]-2-methylpropanamide

Molecular Weight

970.18

Molecular Formula

C50H68N7O9PSi

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)O[Si](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?/m1/s1

InChIKey

PGJKESPHANLWME-FTZVBZPOSA-N

Purity

≥98% by HPLC

Appearance

White to yellow solid

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.