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L-Uridine Sale

(Synonyms: L-尿苷) 目录号 : GC61695

L-Uridine分离自PolyporaceaefungusPoriacocos(Schw.),是正常RNA成分中的D-尿苷的对映异构体。L-Uridine充当核苷磷酸转移酶的磷酸受体。

L-Uridine Chemical Structure

Cas No.:26287-69-4

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5 mg
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产品描述

L-Uridine, isolated from the Polyporaceae fungus Poria cocos (Schw.), is an enantiomer of the normal RNA constituent D-uridine. L-uridine acts as a phosphate acceptor for nucleoside phosphotransferases[1].

[1]. A F Wu, et al. L-uridine: synthesis and behavior as enzyme substrate. Proc Natl Acad Sci U S A. 1969 Aug;63(4):1222-6. [2]. Yumei Wang, et al. Chemical Composition and Pharmacology Research Progress of Shenlingbaizhu Powder. 2019 Asia-Pacific Conference on Clinical Medicine and Public Health.

Chemical Properties

Cas No. 26287-69-4 SDF
别名 L-尿苷
Canonical SMILES O[C@@H]1[C@](N2C(NC(C=C2)=O)=O)([H])O[C@H]([C@@H]1O)CO
分子式 C9H12N2O6 分子量 244.2
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Research Update

L-Uridine: synthesis and behavior as enzyme substrate

Proc Natl Acad Sci U S A 1969 Aug;63(4):1222-6.PMID:5260923DOI:10.1073/pnas.63.4.1222.

L-Uridine, the enantiomer of the normal RNA constituent D-uridine, was synthesized from L-ribose through coupling with bis(trimethylsilyl)-uracil. The synthetic product had the expected chemical and physical characteristics. When used as the acceptor for phosphate transfer by the nucleoside phosphotransferase of carrot, L-Uridine is converted to 5'-L-uridylic acid. The Michaelis constants K(m) are 28 x 10(-3)M for L-Uridine, 5 x 10(-3)M for D-uridine. The nucleoside phosphotransferase of human prostate, which phosphorylates D-uridine in the 5', 3', or 2' positions, fails to transfer phosphate to the 2' position of L-Uridine, but does produce 5'-and 3'-L-uridylic acids.

Metabolism of pyrimidine L-nucleosides

Nucleic Acids Res 1976 Aug;3(8):2143-54.PMID:967691DOI:10.1093/nar/3.8.2143.

The intraperitoneal application of L-nucleosides (L-Cyd, L-Urd, L-dThd) to mice results in distribution of these compounds into tissues of the organism and their gradual excretion in the unchanged form. The residual level has been observed with L-ribonucleosides only and contains in addition to the L-nucleoside its 5'-phosphate. The phosphorylation in vivo is catalyzed by nucleoside-kinase and utilizes ATP as the phosphate donor while glycerol 1-phosphate and creatine phosphate are inactive. The L-cytidine derivatives are in vivo deaminated to the derivatives of L-Uridine. On the other hand, when L-Uridine is applied in vivo, derivatives of L-cytidine are obtained on the level of both the nucleoside and 5'-ribonucleotide.

First synthesis of L-enantio-uracil dinucleotide

Nucleic Acids Res Suppl 2003;(3):33-4.PMID:14510366DOI:10.1093/nass/3.1.33.

L-Enantio-uracil dinucleotide, which consists of two L-uridylic acids and one pyrophosphate, was synthesized for the first time in our laboratory. Benzolyated L-Uridine was prepared by a steroselective glycosylation of silylated uracil with L-1-acetoxy-2,3,5-tri-O-benzoylribose (L-ABR). After deprotection, L-Uridine was converted to L-UP4U by the treatment of L-UMP morpholidate with triethyammonium pyrophosphate (TEA-PPi). Spectral data of synthesized L-UP4U are given in a reference. All spectral data were identical with those of the D-enantiomer except the optical rotation. It showed a positive value compared to the D-enantiomer having a negative value.

Selectivity of montmorillonite catalyzed prebiotic reactions of D, L-nucleotides

Orig Life Evol Biosph 2007 Feb;37(1):3-26.PMID:17160436DOI:10.1007/s11084-006-9013-x.

The montmorillonite-catalyzed reactions of the 5'-phosphorimidazolides of D, L-adenosine (D, L-ImpA) (Figure 1a. N = A, R = H) and D, L-Uridine (Figure 1a., N = U, R = H) yields oligomers that were as long as 7 mers and 6 mers, respectively. The reactions of dilute solutions of D-ImpA and D-ImpU under the same conditions gave oligomers as long as 9 and 8 mers respectively. This demonstrated that oligomer formation is only partially inhibited by incorporation of both the D- and L-enantiomers. The structures of the dimers, trimers and tetramer fractions formed from D, L-ImpA was investigated by selective enzymatic hydrolysis, comparison with authentic samples and mass spectrometry. Homochiral products were present in greater amounts than would be expected if theoretical amounts of each were formed. The ratio of the proportion of homochiral products to that of the amount of each expected for the dimers (cyclic and linear), trimers and tetramers, was 1.3, 1.6, and 2.1, respectively. In the D, L-ImpU reaction homochiral products did not predominate with ratios of dimers (cyclic and linear), trimers and tetramers 0.8, 0.44, and 1.4, respectively. The proportions of cyclic dimers in the dimer fraction were 52-66% with D, L-ImpA and 44-69% with D, L-ImpU. No cyclic dimers were formed in the absence of montmorillonite. The differences in the reaction products of D, L-ImpA and D, L-ImpU are likely to be due to the difference in the orientations of the activated monomers when bound to the catalytic sites on montmorillonite. The consequences of the selectivity of montmorillonite as a prebiotic catalyst are discussed.