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1
Pyrimidine nucleoside analogues.X. 5-Substituted 1-(1,3-dihydroxypropyl-2) uracils.嘧啶核苷类似物。X. 5-取代的1-(1,3-二羟基丙基-2)尿嘧啶
Nucleic Acids Res. 1976 Mar;3(3):721-7. doi: 10.1093/nar/3.3.721.
2
Model studies of thymidylate synthetase. Intramolecular catalysis of 5-hydrogen exchange and 5-hydroxymethylation of 1-substituted uracils.
Biochemistry. 1973 Jun 19;12(13):2416-24. doi: 10.1021/bi00737a008.
3
NMR spectroscopy of the ring nitrogen protons of uracil and substituted uracils; relevance to A psi base pairing in the solution structure of transfer RNA.尿嘧啶及取代尿嘧啶环氮质子的核磁共振光谱；与转运核糖核酸溶液结构中Aψ碱基配对的相关性
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4
A convenient procedure for formation of certain uracil and thymine anhydronucleosides.
Carbohydr Res. 1975 Jul;42(2):379-81. doi: 10.1016/s0008-6215(00)84283-4.
5
Conformation of nucleosides. Dipole moments of pyrimidine nucleosides.核苷的构象。嘧啶核苷的偶极矩。
Biochim Biophys Acta. 1974 Aug 29;361(2):131-9.
6
Pyrimidine ribonucleoside phosphorylase activity vs 5- and/or 6-substituted uracil and uridine analogues, including conformational aspects.嘧啶核糖核苷磷酸化酶活性与5-和/或6-取代尿嘧啶及尿苷类似物的关系，包括构象方面。
Biochem Pharmacol. 1982 Mar 15;31(6):1097-102. doi: 10.1016/0006-2952(82)90348-3.
7
Cytosine and cytidine analogues: synthesis and properties of 5-ethylcytosine, 5-ethylcytidine and a number of their derivatives.
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8
Nucleosides. 100. General synthesis of pyrimidine C-5 cucleosides related to pseudouridine. Synthesis of 5-(beta-D-ribofuranosyl) isocytosine (pseudoisocytidine),5-(beta-D-ribofuranosyl)-2-thiouracil(2-thiopseudouridine) and 5-(beta-D-ribofuranosyl)uracil(pseudouridine).核苷。100. 与假尿苷相关的嘧啶C-5核苷的一般合成。5-(β-D-呋喃核糖基)异胞嘧啶（假异胞苷）、5-(β-D-呋喃核糖基)-2-硫尿嘧啶（2-硫代假尿苷）和5-(β-D-呋喃核糖基)尿嘧啶（假尿苷）的合成。
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9
5-substituted arabinofuranosyluracil nucleosides: synthesis and antiviral properties.5-取代阿拉伯呋喃糖基尿嘧啶核苷：合成与抗病毒特性
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10
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Biochim Biophys Acta. 1976 Feb 18;425(1):115-24. doi: 10.1016/0005-2787(76)90221-5.

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1
Synthesis of phosphoramidites of isoGNA, an isomer of glycerol nucleic acid.异鸟苷磷酸酰胺的合成，甘油核酸的一种异构体。
Beilstein J Org Chem. 2014 Sep 8;10:2131-8. doi: 10.3762/bjoc.10.220. eCollection 2014.

本文引用的文献

1
NONCLASSICAL ANTIMETABOLITES. 18. SIMULATION OF 5'-PHOSPHORIBOSYL BINDING. II. OMEGA-URACIL ALKANOIC ACIDS RELATED TO 2'-DEOXYURIDYLATE.非经典抗代谢物。18. 5'-磷酸核糖结合的模拟。II. 与2'-脱氧尿苷酸相关的ω-尿嘧啶链烷酸
J Pharm Sci. 1965 Jan;54:25-30. doi: 10.1002/jps.2600540107.
2
[Synthesis and properties of polynucleotide analogs based on N1-(1,4-dioxybutyl-2)-thymine].
Dokl Akad Nauk SSSR. 1975;221(2):473-6.

嘧啶核苷类似物。X. 5-取代的1-(1,3-二羟基丙基-2)尿嘧啶

Pyrimidine nucleoside analogues.X. 5-Substituted 1-(1,3-dihydroxypropyl-2) uracils.

作者信息

Hiller S A, Zarin D E, Zhuk R A

出版信息

Nucleic Acids Res. 1976 Mar;3(3):721-7. doi: 10.1093/nar/3.3.721.

DOI:10.1093/nar/3.3.721
PMID:5709
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC342936/
Abstract

A convenient method is suggested for synthesis of uracil-1-malonic acid diethyl ester by alkylating 2,4-bis(trimethylsilyl) uracil with bromo-malonic acid diethyl ester. This compound has been shown to hydrolyze with NaOH yielding either uracil or uracil-1-acetic acid, depending on reaction conditions. Similarly, thymine-1-malinic acid diethyl ester and 5-fluorouracil-1,3-dimalonic acid tetraethyl ester were obtained. 1-(1,3-Dihydroxypropyl)uracil has been obtained by reducing uracil-1-malonic acid diethyl ester with NaBH4.

摘要

提出了一种通过用溴代丙二酸二乙酯烷基化2,4-双（三甲基硅基）尿嘧啶来合成尿嘧啶-1-丙二酸二乙酯的简便方法。已证明该化合物在氢氧化钠作用下水解，根据反应条件可生成尿嘧啶或尿嘧啶-1-乙酸。同样，得到了胸腺嘧啶-1-丙二酸二乙酯和5-氟尿嘧啶-1,3-二丙二酸四乙酯。用硼氢化钠还原尿嘧啶-1-丙二酸二乙酯得到了1-（1,3-二羟基丙基）尿嘧啶。