N4-acetyl-2'-O-methylcytidine

N4-acetyl-2'-O-methylcytidine - CAS 113886-71-8

Catalog number: BRB-002

N4-acetyl-2'-O-methylcytidine is an innovative and scientifically advanced compound, emerging as a groundbreaking solution for studying RNA virus-induced viral afflictions. By specifically pinpointing viral enzymes or obstructing viral replication, it manifests remarkable antiviral attributes.

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Synonyms
Cytidine, N-acetyl-2'-O-methyl-; N4-Ac-2'-OMe-rC; N4-Acetyl-2'-O-methyl cytidine; N-Acetyl-2'-O-methylcytidine; N-(1-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide
CAS
113886-71-8
IUPAC Name
N-[1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
Molecular Weight
299.28
Molecular Formula
C12H17N3O6
Canonical SMILES
CC(=O)NC1=NC(=O)N(C=C1)C2C(C(C(O2)CO)O)OC
InChI
InChI=1S/C12H17N3O6/c1-6(17)13-8-3-4-15(12(19)14-8)11-10(20-2)9(18)7(5-16)21-11/h3-4,7,9-11,16,18H,5H2,1-2H3,(H,13,14,17,19)/t7-,9-,10-,11-/m1/s1
InChIKey
CYDFBLGNJUNSCC-QCNRFFRDSA-N
Purity
≥97% by HPLC
Density
1.58±0.1 g/cm3 (Predicted)
Solubility
Soluble in Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
Appearance
White to Yellow Solid
Storage
Store at -20°C under inert atmosphere
Symbol
ac4Cm

Chemical Structure:

Reference Reading

1. 5S rRNA modification in the hyperthermophilic archaea Sulfolobus solfataricus and Pyrodictium occultum
E Bruenger, J A Kowalak, Y Kuchino, J A McCloskey, H Mizushima, K O Stetter, P F Crain. FASEB J. 1993 Jan;7(1):196-200. doi: 10.1096/fasebj.7.1.8422966.
The 5S rRNAs from Sulfolobus solfataricus and Pyrodictium occultum were digested to nucleosides and analyzed using directly-combined HPLC/mass spectrometry. P. occultum 5S rRNA contains two modified nucleoside species, N4-acetylcytidine (ac4C) and N4-acetyl-2'-O-methylcytidine (ac4Cm). Oligonucleotides were generated from P. occultum 5S rRNA by RNase T1 hydrolysis, and their molecular weights were determined using electrospray mass spectrometry and compared with those predicted from the P. occultum 5S RNA gene sequence. Deviation in mass between expected and observed molecular weights permitted ac4Cm to be located at position 35, in the nonanucleotide CAA-CACC[ac4Cm]G, and the ac4C in one or both of two (C,U)G trinucleotides. 2'-O-Methylcytidine is unambiguously characterized in S. solfataricus 5S rRNA, confirming earlier tentative assignments at the analogous sequence position (Stahl, D.A., Luehrsen, K.R., Woese, C.R., and Pace, N.R. (1981) Nucleic Acids Res., Vol. 9, pp. 6129-6137; Dams, E., Londei, P., Cammarano, P., Vandenberghe, A., and De Wachter, R. (1983) Nucleic Acids Res. Vol. 11, pp. 4667-4676). Potential effects of the presence of ac4C and ac4Cm on thermal stabilization of 5S rRNA in thermophiles are discussed.
2. The role of posttranscriptional modification in stabilization of transfer RNA from hyperthermophiles
J A Kowalak, J J Dalluge, J A McCloskey, K O Stetter. Biochemistry. 1994 Jun 28;33(25):7869-76. doi: 10.1021/bi00191a014.
The influence of posttranscriptional modification on structural stabilization of tRNA from hyperthermophilic archaea was studied, using Pyrococcus furiosus (growth optimum 100 degrees C) as a primary model. Optical melting temperatures (Tm) of unfractionated tRNA in 20 mM Mg2+ are 97 degrees C for P. furiosus and 101.5 degrees C for Pyrodictium occultum (growth optimum, 105 degrees C). These values are approximately 20 degrees C higher than predicted solely from G-C content and are attributed primarily to posttranscriptional modification. Twenty-three modified nucleosides were determined in total digests of P. furiosus tRNA by combined HPLC-mass spectrometry. From cells cultured at 70, 85, and 100 degrees C, progressively increased levels of modification were observed within three families of nucleosides, the most highly modified forms of which were N4-acetyl-2'-O-methylcytidine (ac4Cm), N2,N2,2'-O-trimethylguanosine (m2(2)Gm), and 5-methyl-2-thiouridine (m5s2U). Nucleosides ac4Cm and m2(2)Gm, which are unique to the archaeal hyperthermophiles, were shown in earlier NMR studies to exhibit unusually high conformational stabilities that favor the C3'-endo form [Kawai, G., et al. (1991) Nucleic Acids Symp. Ser. 21, 49-50; (1992) Nucleosides Nucleotides 11, 759-771]. The sequence location of m5s2U was determined by mass spectrometry to be primarily at tRNA position 54, a site of known thermal stabilization in the bacterial thermophile Thermus thermophilus [Horie, N., et al. (1985) Biochemistry 24, 5711-5715]. It is concluded that selected posttranscriptional modifications in archaeal thermophiles play major stabilizing roles beyond the effects of Mg2+ binding and G-C content, and are proportionally more important and have evolved with greater structural diversity at the nucleoside level in the bacterial thermophiles.
3. Relation between functions and conformational characteristics of modified nucleosides found in tRNAs
G Kawai, H Ue, M Yasuda, K Sakamoto, T Hashizume, J A McCloskey, T Miyazawa, S Yokoyama. Nucleic Acids Symp Ser. 1991;(25):49-50.
Conformational characteristics of N4-acetyl-2'-O-methylcytidine (ac4Cm), 5-methyl-2'-O-methylcytidine (m5Cm) and N2-dimethyl-2'-O-methylguanosine (m2(2)Gm) found in tRNAs from extremely thermophilic archaebacteria were analyzed by proton NMR spectroscopy. The 2'-O-methylation of ac4C, m5C and m2(2)G was found to stabilize the C3'-endo form and therefore cause "conformational rigidity". In particular, the ac4Cm was found to be extremely rigid due to additive effects of the N4-acetylation and 2'-O-methylation. Therefore, tRNAs from the extremely thermophilic archaebacteria use the base modifications in combination with the 2'-O-methylation, resulting in stabilization of the A-type conformation at specific positions in the tRNAs even at very high temperatures. In contrast, mesophile tRNAs use for a given site only one of these ribose and base modifications each of which is effective enough by itself at ordinary temperatures. These findings are consistent with our previous findings that roles of a variety of post-transcriptional modifications are to regulate the conformational rigidity/flexibility which is essential for the tRNA functions.
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