1-(2'-Deoxy-5'-O-DMT-2'-fluoro-b-D-arabinofuranosyl)uracil 3'-CE-phosphoramidite

1-(2'-Deoxy-5'-O-DMT-2'-fluoro-b-D-arabinofuranosyl)uracil 3'-CE-phosphoramidite - CAS 1190089-70-3

Catalog number: BRA-007

1-(2'-Deoxy-5'-O-DMT-2'-fluoro-b-D-arabinofuranosyl)uracil 3'-CE-phosphoramidite is a novel nucleotide monophosphate with antiviral and anticancer properties.

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Synonyms
2'-Fluoro-2'-deoxy-ara-U-3'-phosphoramidite; 5'-O-(4,4'-Dimethoxytrityl)-2'-deoxy-2'-fluoro-b-D-arabinouridine-3'-CEN-phosphoramidite; 5'-O-DMT-2'-F-2'-arabinofuranosyl-deoxyuridine 3'-CE phosphoramidite; 2,4(1H,3H)-Pyrimidinedione, 1-[5-O-[bis(4-methoxyphenyl)phenylmethyl]-3-O-[[bis(1-methylethyl)amino](2-cyanoethoxy)phosphino]-2-deoxy-2-fluoro-α-D-arabinofuranosyl]-; 2'-ara-2'-F-2'-dU Phosphoramidite
CAS
1190089-70-3
IUPAC Name
3-[[(2R,3R,4S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(2,4-dioxopyrimidin-1-yl)-4-fluorooxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
Molecular Weight
748.78
Molecular Formula
C39H46FN4O8P
Canonical SMILES
CC(C)N(C(C)C)P(OCCC#N)OC1C(OC(C1F)N2C=CC(=O)NC2=O)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC
InChI
InChI=1S/C39H46FN4O8P/c1-26(2)44(27(3)4)53(50-24-10-22-41)52-36-33(51-37(35(36)40)43-23-21-34(45)42-38(43)46)25-49-39(28-11-8-7-9-12-28,29-13-17-31(47-5)18-14-29)30-15-19-32(48-6)20-16-30/h7-9,11-21,23,26-27,33,35-37H,10,24-25H2,1-6H3,(H,42,45,46)/t33-,35+,36-,37-,53?/m1/s1
InChIKey
HQHQPAYRJJMYQX-CPBIVIIKSA-N
Purity
≥95%

Chemical Structure:

Reference Reading

1. Innovative antimicrobial substances based on uracil S-derivatives
Svetlana Meshcheryakova, Alina Shumadalova, Ozal Beylerli, Ilgiz Gareev, Shiguang Zhao, Jianing Wu. Drug Dev Res. 2022 May;83(3):578-585. doi: 10.1002/ddr.21886.
The problem of antimicrobial resistance is an important global public health challenge. We propose that a development of new antibiotic compounds around known natural substances is a solution to this problem. We investigate reengineer natural products into potent antibiotics. Uracil fragment is abundant in nature and significant to treat infectious diseases due to its affection to the replication of the bacterial chromosome. 12 new uracil S-derivatives were obtained and tested for their in vitro antimicrobial properties. N3 -(thietan-3-yl)- and N3 -(1,1-dioxothietan-3-yl)uracils derivatives were synthesized by thietanylation of 6-methyluracil with 2-chloromethylthiirane and subsequent oxidation of the thietan ring. A method of their alkylation with ethyl-2-chloroacetate was developed and acetohydrazides containing 3-(thietan-3-yl)- and 3-(1,1-dioxothietan-3-yl)uracilyls fragments in the acetyl group were obtained by hydrazinolysis of 2-(thietanyluracil-1-yl)acetic acid ethyl esters. Their interaction with β-dicarbonyl compounds, anhydride of mono- and dicarboxylic acids was studied. Antimicrobial activity was determined by the agar diffusion method on test organisms: S. aureus, E. coli, P. vulgaris, K. pneumoniae, C. diversus, E. aerogenes, P. aeruginosa, S. abosit. N-acyl-5-hydroxypyrazolines and N,N'-diacylhydrazines of 6-methyluracil thietanyl- and dioxothietanyl derivatives showed high antimicrobial activity, which is consistent with the results of structure activity relationship analysis (MIC 0.1-10 μg/ml).
2. Synthesis of 5-acyl-6-[2-hydroxy-3-(amino)propylamino]-1,3-dialkyl-1H-pyrimidine-2,4-diones
Palwinder Singh, Kamaldeep Paul, Wolfgang Holzer. Org Biomol Chem. 2005 Nov 7;3(21):3958-65. doi: 10.1039/b509775d.
A stepwise synthetic approach involving substitution of 6-chloro-1,3-dialkyluracils (5 and 6) with 3-(tert-amino)-2-hydroxypropylamines and subsequent acylation at C5 of uracil has been used to synthesize pyrimidinediones 27-33 in 61-89% overall yield. The conformational aspects of the new molecules based upon NMR data have been discussed.
3. 3-Methylation alters excited state decay in photoionised uracil
Javier Segarra-Martí, Thierry Tran, Michael J Bearpark. Phys Chem Chem Phys. 2022 Nov 18;24(44):27038-27046. doi: 10.1039/d2cp03460c.
UV and VUV-induced processes in DNA/RNA nucleobases are central to understand photo-damaging and photo-protecting mechanisms in our genetic material. Here we model the events following photoionisation and electronic excitation in uracil, methylated in the 1' and 3' positions, using the correlated XMS-CASPT2 method. We compare our results against those for uracil and 5-methyl-uracil (thymine) previously published. We find 3-methylation, an epigenetic modification in non-negligible amounts, shows the largest differences in photoionised decay of all three derivatives studied compared to uracil itself. At the S0 minimum, 3-methyl-uracil (3mUra) shows almost degenerate excited cation states. Upon populating the cation manifold, a crossing is predicted featuring different topography compared to other methylated uracil species in this study. We find an effective 3-state conical intersection accessible for 3mUra+, which points towards an additional pathway for radiationless decay. 3-Methylation reduces the potential energy barrier mediating decay to the cation ground state, making it vanish and leading to a pathway that we expect will contribute to the fastest radiationless decay amongst all methylated uracil species studied to date. 1- and 5-methylation, on the other hand, give differences from uracil in detail only: ionisation potentials are slightly red-shifted and the potential energy barrier mediating decay to the cation ground state is small but almost unchanged. By comparing against CASSCF calculations, we establish XMS-CASPT2 is essential to correctly describe conical intersections for 3mUra+. Our calculations show how a chemical modification that seems relatively small electronically can nevertheless have a significant impact on the behaviour of electronic excited states: a single methylation in the 3' position alters the behaviour of the RNA base uracil and appears to open an additional pathway for radiationless decay following ionisation and electronic excitation.
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