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L-尿苷:作为酶底物的合成及特性

L-uridine: synthesis and behavior as enzyme substrate.

作者信息

Wu A F, Chargaff E

出版信息

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

DOI:10.1073/pnas.63.4.1222
PMID:5260923
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC223453/
Abstract

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.

摘要

L-尿苷是正常RNA成分D-尿苷的对映体,它由L-核糖与双(三甲基硅基)尿嘧啶偶联合成。合成产物具有预期的化学和物理特性。当用作胡萝卜核苷磷酸转移酶进行磷酸转移的受体时,L-尿苷会转化为5'-L-尿苷酸。米氏常数K(m)对于L-尿苷为28×10⁻³M,对于D-尿苷为5×10⁻³M。人前列腺的核苷磷酸转移酶可将D-尿苷在5'、3'或2'位磷酸化,但无法将磷酸转移至L-尿苷的2'位,不过确实能产生5'-和3'-L-尿苷酸。

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引用本文的文献

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本文引用的文献

1
STUDIES ON SYNTHETIC NUCLEOSIDES. IV. A NEW SYNTHETIC METHOD OF PYRIMIDINE AND PURINE RIBOSIDES.合成核苷的研究。IV.嘧啶和嘌呤核糖核苷的一种新合成方法。
Chem Pharm Bull (Tokyo). 1964 Dec;12:1471-8. doi: 10.1248/cpb.12.1471.
2
On the synthesis of nucleotides by nucleoside phosphotransferases.
Biochim Biophys Acta. 1954 Dec;15(4):549-59. doi: 10.1016/0006-3002(54)90013-x.
3
Estimation of nucleic acids.核酸的测定
Methods Biochem Anal. 1954;1:287-305. doi: 10.1002/9780470110171.ch11.
4
Spectrophotometric studies of nucleic acid derivatives and related compounds as a function of pH. II. Natural and synthetic pyrimidine nucleosides.核酸衍生物及相关化合物作为pH函数的分光光度研究。II. 天然和合成嘧啶核苷。
Biochim Biophys Acta. 1952 Oct;9(4):369-84. doi: 10.1016/0006-3002(52)90181-9.
5
Purification and properties of a nucleoside phosphotransferase from carrot.胡萝卜中一种核苷磷酸转移酶的纯化及性质
J Biol Chem. 1967 Oct 25;242(20):4834-40.
6
Studies on synthetic nucleosides. I. Trimethylsilyl derivatives of pyrimidines and purines.
Chem Pharm Bull (Tokyo). 1964 Mar;12(3):352-6. doi: 10.1248/cpb.12.352.
7
Studies on synthetic nucleotides. IV. Preparation of L-beta-ribonucleosides and L-beta-ribonucleotides.
Chem Pharm Bull (Tokyo). 1967 Dec;15(12):1863-70. doi: 10.1248/cpb.15.1863.