(S)-5-(Carboxyhydroxymethyl)uridine
(S)-5-(Carboxyhydroxymethyl)uridine, a highly bioactive compound widely utilized in the biomedical industry, has garnered considerable attention due to its remarkable potential in therapeutic applications against a range of diseases, including cancer, viral infections, and neurodegenerative disorders. Extensive research has revealed its impressive anti-tumor and anti-viral properties, rendering it an invaluable asset for the advancement of drug discovery and biomedical research. Its multifaceted capabilities highlight the significant role it plays in the pursuit of improved healthcare and scientific exploration.
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Synonyms
5-Pyrimidineacetic acid, 1,2,3,4-tetrahydro-a-hydroxy-2,4-dioxo-1-b-D-ribofuranosyl-, (S)-; 5-Pyrimidineacetic acid, 1,2,3,4-tetrahydro-α-hydroxy-2,4-dioxo-1-β-D-ribofuranosyl-, (αS)-; (αS)-1,2,3,4-Tetrahydro-α-hydroxy-2,4-dioxo-1-β-D-ribofuranosyl-5-pyrimidineacetic acid; (S)-2-(1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-2-hydroxyacetic acid
IUPAC Name
(S)-2-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]-2-hydroxyacetic acid
Molecular Formula
C11H14N2O9
Canonical SMILES
O=C(O)C(O)C1=CN(C(=O)NC1=O)C2OC(CO)C(O)C2O
InChI
InChI=1S/C11H14N2O9/c14-2-4-6(16)7(17)9(22-4)13-1-3(5(15)10(19)20)8(18)12-11(13)21/h1,4-7,9,14-17H,2H2,(H,19,20)(H,12,18,21)/t4-,5+,6-,7-,9-/m1/s1
InChIKey
UVGCZRPOXXYZKH-XLKNOJSPSA-N
Related CAS
934743-11-0 (5-(Carboxyhydroxymethyl)uridine) 127911-55-1 ((R)-5-(Carboxyhydroxymethyl)uridine)
Chemical Structure:
Reference Reading
1. Determination of structure and absolute configuration of a new modified nucleoside isolated from tRNA-2Gly of Bombyx mori by a total synthesis to be 5-(S-carboxy(hydroxy)methyl) uridine
T Kondo, T Fukami, T Goto, M Kawakami, S Takemura. Nucleic Acids Symp Ser. 1983;(12):127-30.
A synthesis of a new modified nucleoside isolated from tRNA2Gly of Bombyx mori was accomplished. This synthesis confirmed its structure and proved its absolute configuration to be 5-(S-carboxy(hydroxy)methyl)uridine.
2. 5-(Carboxy-hydroxymethyl)uridine, a new modified nucleoside located in the anticodon of tRNA2Gly from the posterior silk glands of Bombyx mori
M Kawakami, K Nishio, S Takemura, T Kondo, T Goto. Nucleic Acids Symp Ser. 1979;(6):s53-5.
A new modified nucleoside located in the anticodon of tRNA2Gly from the posterior silk glands of Bombyx mori has been isolated and its structure determined as 5-(carboxy-hydroxymethyl)uridine mainly by analyses of its UV, 1H NMR, and FD mass spectra.
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