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1
Synthesis of fluorescent nucleotide analogues: 5'-mono-, di-, and triphosphates of linear-benzoguanosine, linear-benzoinosine, and linear-benzoxanthosine.荧光核苷酸类似物的合成:线性苯并鸟苷、线性苯并肌苷和线性苯并黄苷的5'-单磷酸、二磷酸和三磷酸。
Proc Natl Acad Sci U S A. 1979 Sep;76(9):4262-4. doi: 10.1073/pnas.76.9.4262.
2
Ribonucleoside 3'-di- and -triphosphates. Synthesis of guanosine tetraphosphate (ppGpp).核糖核苷3'-二磷酸和-三磷酸。鸟苷四磷酸(ppGpp)的合成。
Biochemistry. 1975 Mar 11;14(5):981-8. doi: 10.1021/bi00676a017.
3
Profiles of purine biosynthesis, salvage and degradation in disks of potato (Solanum tuberosum L.) tubers.马铃薯(Solanum tuberosum L.)块茎圆盘内嘌呤生物合成、补救途径及降解的概况
Planta. 2006 Dec;225(1):115-26. doi: 10.1007/s00425-006-0334-9. Epub 2006 Jul 15.
4
Fluorescent guanosine-nucleotide analogs suitable for photoaffinity-labeling experiments.适用于光亲和标记实验的荧光鸟苷酸类似物。
Eur J Biochem. 1976 Jun 1;65(2):473-9. doi: 10.1111/j.1432-1033.1976.tb10363.x.
5
Imidazo(1,2-c)pyrimidine nucleosides. Synthesis of N-bridgehead inosine monophosphate and guanosine monophosphate analogues related to 3-deazapurines.咪唑并(1,2 - c)嘧啶核苷。与3 - 脱氮嘌呤相关的N - 桥头肌苷一磷酸和鸟苷一磷酸类似物的合成。
J Org Chem. 1975 Dec 12;40(25):3708-13. doi: 10.1021/jo00913a019.
6
[Pathways of inosine monophosphate transformation in the chicken liver].[鸡肝脏中肌苷单磷酸的转化途径]
Biokhimiia. 1988 Feb;53(2):182-7.
7
Azidopolynucleotides as photoaffinity reagents.叠氮多核苷酸作为光亲和试剂。
Nucleic Acids Res. 1980 Apr 11;8(7):1675-91. doi: 10.1093/nar/8.7.1675.
8
Spectroscopic sensitivity of linear-benzoadenine nucleotides to divalent metal counterions, side chain conformations, micelles, and enzymes.线性苯并腺嘌呤核苷酸对二价金属抗衡离子、侧链构象、胶束和酶的光谱敏感性。
Proc Natl Acad Sci U S A. 1978 Sep;75(9):4204-8. doi: 10.1073/pnas.75.9.4204.
9
8-(p-CF3-cinnamyl)-modified purine nucleosides as promising fluorescent probes.8-(p-CF3-cinnamyl)-修饰的嘌呤核苷作为有前途的荧光探针。
Org Biomol Chem. 2011 Oct 26;9(22):7763-73. doi: 10.1039/c1ob05681f. Epub 2011 Sep 29.
10
Comparative study of the structure and conformation in aqueous solution of the antileukemic agent 6-thiopurine ribonucleoside 5'-phosphate to that of common purine 5'-nucleotides.抗白血病药物6-硫代嘌呤核糖核苷5'-磷酸与普通嘌呤5'-核苷酸在水溶液中的结构和构象比较研究。
J Am Chem Soc. 1975 May 28;97(11):3215-8. doi: 10.1021/ja00844a049.

引用本文的文献

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Artificial genetic sets composed of size-expanded base pairs.由尺寸扩展碱基对组成的人工遗传集。
Angew Chem Int Ed Engl. 2013 Nov 25;52(48):12498-508. doi: 10.1002/anie.201305267. Epub 2013 Nov 7.
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The components of xRNA: synthesis and fluorescence of a full genetic set of size-expanded ribonucleosides.xRNA 的组成部分:大小扩展核糖核苷的全基因集合的合成和荧光。
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Synthesis and properties of size-expanded DNAs: toward designed, functional genetic systems.尺寸扩展DNA的合成与性质:迈向设计的功能性遗传系统
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本文引用的文献

1
Spectroscopic sensitivity of linear-benzoadenine nucleotides to divalent metal counterions, side chain conformations, micelles, and enzymes.线性苯并腺嘌呤核苷酸对二价金属抗衡离子、侧链构象、胶束和酶的光谱敏感性。
Proc Natl Acad Sci U S A. 1978 Sep;75(9):4204-8. doi: 10.1073/pnas.75.9.4204.
2
Fluorescence spectroscopy of proteins.蛋白质的荧光光谱学
Science. 1968 Nov 1;162(3853):526-33. doi: 10.1126/science.162.3853.526.
3
The reaction of guanosine and deoxyguanosine with glycidaldehyde.鸟苷和脱氧鸟苷与缩水甘油醛的反应。
Tetrahedron Lett. 1968 Feb;13:1583-6. doi: 10.1016/s0040-4039(01)99007-0.
4
Studies of transfer RNA tertiary structure by singlet-singlet energy transfer.通过单重态-单重态能量转移对转运RNA三级结构的研究。
Proc Natl Acad Sci U S A. 1970 Jan;65(1):39-46. doi: 10.1073/pnas.65.1.39.
5
The determination of the molecular weight of ribonucleic acid by polyacrylamide-gel electrophresis. The effects of changes in conformation.通过聚丙烯酰胺凝胶电泳测定核糖核酸的分子量。构象变化的影响。
Biochem J. 1969 Jun;113(1):131-8. doi: 10.1042/bj1130131.
6
Energy transfer in tRNA phe (yeast). The solution structure of transfer RNA.酵母苯丙氨酸转运核糖核酸中的能量转移。转运核糖核酸的溶液结构。
Biopolymers. 1974;13(8):1607-20. doi: 10.1002/bip.1974.360130808.
7
Fluorescent modification of guanine. Reaction with substituted malondialdehydes.鸟嘌呤的荧光修饰。与取代丙二醛的反应。
J Org Chem. 1976 Jan 23;41(2):294-300. doi: 10.1021/jo00864a023.
8
Linear benzoadenine. A stretched-out analog of adenine.线性苯并腺嘌呤。腺嘌呤的一种伸展类似物。
J Org Chem. 1975 Feb 7;40(3):356-63. doi: 10.1021/jo00891a021.
9
Fluorescent nucleosides and nucleotides.荧光核苷和核苷酸。
Ann N Y Acad Sci. 1975 Aug 8;255:43-58. doi: 10.1111/j.1749-6632.1975.tb29212.x.
10
Defined dimensional changes in enzyme substrates and cofactors. Synthesis of lin-benzoadenosine and enzymatic evaluation of derivatives of the benzopurines.酶底物和辅因子中确定的尺寸变化。线性苯并腺苷的合成及苯并嘌呤衍生物的酶促评估。
J Am Chem Soc. 1976 Jun 23;98(13):3987-94. doi: 10.1021/ja00429a040.

荧光核苷酸类似物的合成:线性苯并鸟苷、线性苯并肌苷和线性苯并黄苷的5'-单磷酸、二磷酸和三磷酸。

Synthesis of fluorescent nucleotide analogues: 5'-mono-, di-, and triphosphates of linear-benzoguanosine, linear-benzoinosine, and linear-benzoxanthosine.

作者信息

Leonard N J, Keyser G E

出版信息

Proc Natl Acad Sci U S A. 1979 Sep;76(9):4262-4. doi: 10.1073/pnas.76.9.4262.

DOI:10.1073/pnas.76.9.4262
PMID:291962
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC411553/
Abstract

The fluorescent nucleotide analogues (the 5'-mono-, di-, and triphosphates of lin-benzoguanosine, lin-benzoxanthosine, and lin-benzoinosine) have been prepared for use as dimensional probes of enzyme binding sites. They have quantum yields in aqueous solution of 0.39, 0.55, and 0.04 and fluorescent lifetimes of 6, 9, and approximately equal to 1.5 nsec, respectively. lin-Benzoinosine 5'-monophosphate is a substrate for xanthine oxidase (xanthine:oxygen oxidoreductase, EC 1.2.3.2), providing lin-benzoxanthosine 5'-monophosphate, and lin-benzoinosine 5'-diphosphate is a substrate for polynucleotide phosphorylase (polyribonucleotide:orthophosphate nucleotidyltransferase. EC 2.7.7.8), giving poly(lin-benzoinosinic acid). The benzologues of the purine diphosphates are substrates for pyruvate kinase (ATP:pyruvate 2-O-phosphotransferase, EC 2.7.1.40), which is used to prepare the triphosphates.

摘要

荧光核苷酸类似物(连苯并鸟苷、连苯并黄苷和连苯并肌苷的5'-单磷酸、二磷酸和三磷酸)已被制备用作酶结合位点的尺寸探针。它们在水溶液中的量子产率分别为0.39、0.55和0.04,荧光寿命分别为6、9和约1.5纳秒。连苯并肌苷5'-单磷酸是黄嘌呤氧化酶(黄嘌呤:氧氧化还原酶,EC 1.2.3.2)的底物,生成连苯并黄苷5'-单磷酸,连苯并肌苷5'-二磷酸是多核苷酸磷酸化酶(聚核糖核苷酸:正磷酸核苷酸基转移酶,EC 2.7.7.8)的底物,生成聚(连苯并肌苷酸)。嘌呤二磷酸的苯并类似物是丙酮酸激酶(ATP:丙酮酸2-O-磷酸转移酶,EC 2.7.1.40)的底物,该酶用于制备三磷酸。