5'-O-DMT-2'-O-TBDMS-N4-Acetyl-L-Cytidine 3'-CE phosphoramidite - CAS 237060-94-5

Catalog number: BRA-031

5'-O-DMT-2'-O-TBDMS-N4-Acetyl-L-Cytidine 3'-CE phosphoramidite, a remarkable substance within the biomedical field, holds immense significance. Its application in the synthesis of altered oligonucleotides for therapeutic intentions is widespread. Through the specific manipulation and addressing of genetic material, particularly RNA, it exhibits a pivotal role in combating diverse ailments. Boasting an exceptional composition, this product possesses the power to revolutionize precision medicine and propel the progression of targeted therapies.

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Ordering Information

Catalog Number	Size	Price	Stock	Quantity
BRA-031	1 g	$990	In stock

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Synonyms

Acetamide, N-[1-[5-O-[bis(4-methoxyphenyl)phenylmethyl]-3-O-[[bis(1-methylethyl)amino](2-cyanoethoxy)phosphino]-2-O-[(1,1-dimethylethyl)dimethylsilyl]-β-L-ribofuranosyl]-1,2-dihydro-2-oxo-4-pyrimidinyl]-; DMT-2'-O-TBDMS-L-rC(Ac) Phosphoramidite

CAS

237060-94-5

IUPAC Name

N-[1-[(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]-2-oxopyrimidin-4-yl]acetamide

Molecular Weight

902.11

Molecular Formula

C47H64N5O9PSi

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)C)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC

InChI

InChI=1S/C47H64N5O9PSi/c1-32(2)52(33(3)4)62(58-30-16-28-48)60-42-40(59-44(43(42)61-63(11,12)46(6,7)8)51-29-27-41(49-34(5)53)50-45(51)54)31-57-47(35-17-14-13-15-18-35,36-19-23-38(55-9)24-20-36)37-21-25-39(56-10)26-22-37/h13-15,17-27,29,32-33,40,42-44H,16,30-31H2,1-12H3,(H,49,50,53,54)/t40-,42-,43-,44-,62?/m0/s1

InChIKey

QKWKXYVKGFKODW-ZYRNLWDWSA-N

Purity

≥98% by HPLC

Appearance

White to Off-white 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.