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通过磷酸三酯法合成核肽H-Phe-Tyr(pGC)-NH2和H-Phe-Ser(pGC)-Ala-OH。

Synthesis of the nucleopeptides H-Phe-Tyr(pGC)-NH2 and H-Phe-Ser(pGC)-Ala-OH via a phosphotriester approach.

作者信息

Kuyl-Yeheskiely E, Dreef-Tromp C M, Geluk A, van der Marel G A, van Boom J H

机构信息

Gorlaeus Laboratories, Leiden University, The Netherlands.

出版信息

Nucleic Acids Res. 1989 Apr 25;17(8):2897-905. doi: 10.1093/nar/17.8.2897.

DOI:10.1093/nar/17.8.2897
PMID:2726447
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC317700/
Abstract

Use of the protecting groups di-n-butylaminomethylene,2-nitrophenylsulfenyl and the ester of 2-(hydroxymethyl)-9,10-anthraquinone, enabled us for the first time to prepare nucleopeptide fragments containing 2'-deoxyguanosine and a free carboxylic acid group.

摘要

使用保护基团二正丁基氨基亚甲基、2-硝基苯硫基以及2-(羟甲基)-9,10-蒽醌的酯，使我们首次能够制备含有2'-脱氧鸟苷和游离羧酸基团的核苷肽片段。

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1
Synthesis of the nucleopeptides H-Phe-Tyr(pGC)-NH2 and H-Phe-Ser(pGC)-Ala-OH via a phosphotriester approach.通过磷酸三酯法合成核肽H-Phe-Tyr(pGC)-NH2和H-Phe-Ser(pGC)-Ala-OH。
Nucleic Acids Res. 1989 Apr 25;17(8):2897-905. doi: 10.1093/nar/17.8.2897.
2
Synthesis and enzymatic stability of phosphodiester-linked peptide-oligonucleotide hybrids.
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Conformational-energy studies of tetrapeptide opiates. Candidate active and inactive conformations.四肽类阿片药物的构象能研究。候选活性和非活性构象。
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4
Solid-phase synthesis of H-Phe-Tyr-(pATAT)-NH2: a nucleopeptide fragment from the nucleoprotein of bacteriophage phi X174.H-Phe-Tyr-(pATAT)-NH2的固相合成：来自噬菌体phi X174核蛋白的一个核肽片段。
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Delta opioidmimetic antagonists: prototypes for designing a new generation of ultraselective opioid peptides.δ阿片样物质模拟拮抗剂：设计新一代超选择性阿片肽的原型
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Solid-phase synthesis of a nucleopeptide from the linking site of adenovirus-2 nucleoprotein, -Ser(p5'CATCAT)-Gly-Asp-. Convergent versus stepwise strategy.从腺病毒2型核蛋白的连接位点-Ser(p5'CATCAT)-Gly-Asp-固相合成核肽。汇聚法与逐步合成法策略
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Structure-activity relationships of the unique and potent agouti-related protein (AGRP)-melanocortin chimeric Tyr-c[beta-Asp-His-DPhe-Arg-Trp-Asn-Ala-Phe-Dpr]-Tyr-NH2 peptide template.独特且强效的刺鼠相关蛋白（AGRP）-促黑素细胞皮质素嵌合肽Tyr-c[β-天冬氨酸-组氨酸-二苯丙氨酸-精氨酸-色氨酸-天冬酰胺-丙氨酸-苯丙氨酸-二肽基脯氨酸]-Tyr-NH2的构效关系。
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Opioid peptides. Structure-activity relationships in [beta-Ala4]dermorphin tetrapeptides. V.
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Opioid peptides. Structure-activity relationships of dermorphin endothiotetrapeptides. VII.阿片样肽。皮啡肽内硫代四肽的构效关系。VII。
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引用本文的文献

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Studies on the synthesis of nucleotidyl-peptides. II. The preparation of a nucleotidyl-peptide having a 5'-nucleotidyl-(P-O)-serine phosphodiester bond.核苷酸肽的合成研究。II. 具有5'-核苷酸-(P-O)-丝氨酸磷酸二酯键的核苷酸肽的制备。
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Nucleic Acids Res. 1994 Nov 11;22(22):4810-7. doi: 10.1093/nar/22.22.4810.
3
Solid-phase synthesis of a nucleopeptide from the linking site of adenovirus-2 nucleoprotein, -Ser(p5'CATCAT)-Gly-Asp-. Convergent versus stepwise strategy.从腺病毒2型核蛋白的连接位点-Ser(p5'CATCAT)-Gly-Asp-固相合成核肽。汇聚法与逐步合成法策略
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4
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Nucleic Acids Res. 1990 Nov 25;18(22):6491-5. doi: 10.1093/nar/18.22.6491.
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Solid-phase synthesis of the nucleopeptide fragment H-Asp-Ser[pAAAGTAAGCC]-Glu-OH from the nucleoprotein of Bacillus subtilis phage phi 29.来自枯草芽孢杆菌噬菌体phi 29核蛋白的核肽片段H-Asp-Ser[pAAAGTAAGCC]-Glu-OH的固相合成
Nucleic Acids Res. 1992 Aug 11;20(15):4015-20. doi: 10.1093/nar/20.15.4015.
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Solid-phase synthesis of an RNA nucleopeptide fragment from the nucleoprotein of poliovirus.脊髓灰质炎病毒核蛋白RNA核肽片段的固相合成。
Nucleic Acids Res. 1992 May 25;20(10):2435-9. doi: 10.1093/nar/20.10.2435.

本文引用的文献

1
Protein p3 is linked to the DNA of phage phi 29 through a phosphoester bond between serine and 5'-dAMP.蛋白质p3通过丝氨酸与5'-二磷酸腺苷之间的磷酸酯键与噬菌体φ29的DNA相连。
Proc Natl Acad Sci U S A. 1980 Nov;77(11):6425-8. doi: 10.1073/pnas.77.11.6425.
2
Dialkylformamidines: depurination resistant N6-protecting group for deoxyadenosine.二烷基甲脒：用于脱氧腺苷的抗脱嘌呤N6保护基团。
Nucleic Acids Res. 1983 Nov 25;11(22):8031-6. doi: 10.1093/nar/11.22.8031.
3
The bond in the bacteriophage phi X174 gene A protein--DNA complex is a tyrosyl-5'-phosphate ester.噬菌体φX174基因A蛋白与DNA复合物中的键是酪氨酰-5'-磷酸酯。
FEBS Lett. 1984 Aug 6;173(2):351-6. doi: 10.1016/0014-5793(84)80804-2.
4
The 2-nitrophenylsulfenyl (Nps) group for the protection of amino functions of cytidine, adenosine, guanosine and their 2'-deoxysugar derivatives.用于保护胞苷、腺苷、鸟苷及其2'-脱氧糖衍生物氨基功能的2-硝基苯硫基（Nps）基团。
Acta Chem Scand B. 1983;37(9):857-62. doi: 10.3891/acta.chem.scand.37b-0857.
5
A model study directed towards the preparation of nucleopeptides via H-phosphonate intermediates.一项旨在通过H-膦酸酯中间体制备核肽的模型研究。
Nucleic Acids Res. 1987 Feb 25;15(4):1807-18. doi: 10.1093/nar/15.4.1807.
6
Alteration of the ATG start codon of the A protein of bacteriophage phi X174 into an ATT codon yields a viable phage indicating that A protein is not essential for phi X174 reproduction.将噬菌体φX174的A蛋白的ATG起始密码子改变为ATT密码子可产生一种有活力的噬菌体，这表明A蛋白对于φX174的繁殖并非必不可少。
FEBS Lett. 1987 Jun 22;218(1):119-25. doi: 10.1016/0014-5793(87)81030-x.