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1
Seven-membered cyclic phosphate: synthesis and properties of S-cycloadenosine 2',5'-cyclic phosphate and cordycepin 2',5'-cyclic phosphate. Studies of nucleosides and nucleotides. LXIV. 1). Purine cyclonucleosides 25.七元环磷酸酯：S-环腺苷2',5'-环磷酸酯和虫草素2',5'-环磷酸酯的合成与性质。核苷与核苷酸研究。LXIV。1）. 嘌呤环核苷25。
Nucleic Acids Res. 1974 Dec;1(12):1783-98. doi: 10.1093/nar/1.12.1783.
2
Polynucleotides. XXXI1. Synthesis of AUG analogs containing 8,2'-S-cycloadenosine, 8,5'-S-cycloadenosine, 8-bromoadenosin, 8-oxyadenosine and formycin in the first position of the codon.多核苷酸。XXXI1。密码子第一位含8,2'-S-环腺苷、8,5'-S-环腺苷、8-溴腺苷、8-氧代腺苷和间型霉素的AUG类似物的合成。
Nucleic Acids Res. 1975 Aug;2(8):1345-63. doi: 10.1093/nar/2.8.1345.
3
Polynecleotides. XXX. Synthesis and properties of oligonucleotides of cyclouridine phosphate. Hybridization with the oligomer of S-cycloadenosine phosphate to form left-handed helical complexes.
J Am Chem Soc. 1976 Feb 18;98(4):969-73. doi: 10.1021/ja00420a017.
4
Synthesis of 6-O-cyclopyrimidine nucleosides and their physicochemical properties.6-O-环嘧啶核苷的合成及其物理化学性质。
Nucleic Acids Symp Ser. 1979(6):s7-10.
5
Polynucleotides. XXIV. Synthesis and properties of a dinucleoside monophosphate derived from 8,2'-O-cycloadenosine.多核苷酸。二十四。源自8,2'-O-环腺苷的二磷酸核苷单酯的合成与性质
J Am Chem Soc. 1974 Jul 24;96(15):4966-72. doi: 10.1021/ja00822a040.
6
Polynucleotides. XXIV. Synthesis and properties of a dinucleoside monophosphate derived from uridine 6,2-cyclonucleoside.多核苷酸。二十四。源自尿苷6,2-环核苷酸的二核苷单磷酸的合成及性质
Nucleic Acids Res. 1974 Mar;1(3):479-89. doi: 10.1093/nar/1.3.479.
7
Improved synthesis of 32P-labelled 3',5'-cyclic GMP and other 3',5'-cyclic ribo- and deoxyribonucleotides of high specific activity.改进32P标记的3',5'-环鸟苷酸及其他高比活度的3',5'-环核糖核苷酸和脱氧核糖核苷酸的合成。
Biochim Biophys Acta. 1973 Sep 14;320(2):535-9. doi: 10.1016/0304-4165(73)90334-6.
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Cyclization of uridine monophosphate by diethyl pyrocarbonate.焦碳酸二乙酯催化尿苷一磷酸的环化反应。
Nucleic Acids Res. 1975 Jun;2(6):985-92. doi: 10.1093/nar/2.6.985.
9
The synthesis of (32P) adenosine 3',5'-cyclic phosphate and other ribo- and deoxyribonucleoside 3',5'-cyclic phosphates.（32P）腺苷3'，5'-环磷酸酯及其他核糖和脱氧核糖核苷3'，5'-环磷酸酯的合成。
Methods Enzymol. 1974;38:410-20. doi: 10.1016/0076-6879(74)38058-5.
10
The preparation of acylated derivatives of cyclic nucleotides.
Methods Enzymol. 1974;38:399-409. doi: 10.1016/0076-6879(74)38057-3.

引用本文的文献

1
Nucleic acid-like structures. III. Oligomerization of 3'-deoxyadenosine 2',5'-diphosphoimidazolide.类核酸结构。III. 3'-脱氧腺苷2',5'-二磷酸咪唑化物的寡聚化
J Mol Evol. 1987;26(4):291-3. doi: 10.1007/BF02101146.

本文引用的文献

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Studies of nucleosides and nucleotides. XXXII. Purine cyclonucleosides. 3. Synthesis of2 2'-deoxy- and 3'-deoxyadenosine from adenosine.
Chem Pharm Bull (Tokyo). 1967 Jan;15(1):94-100. doi: 10.1248/cpb.15.94.
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Studies of nucleosides and nucleotides. XLI. Purine cyclonucleosides. 8. Selective sulfonylation of 8-bromoadenosine derivatives and an alternate synthesis of 8,2'-and 8,3'-S-cyclonucleosides.
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Synthesis of isosteric phosphonate analogs of some biologically important phosphodiesters.一些具有重要生物学意义的磷酸二酯的等排膦酸酯类似物的合成。
J Am Chem Soc. 1970 Sep 9;92(18):5510-1. doi: 10.1021/ja00721a034.
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Synthesis and biological activity of 9-beta-D-arabinofuranosyladenine cyclic 3',5'-phosphate and 9-beta-D-arabinofuranosylguanine cyclic 3',5'-phosphate.9-β-D-阿拉伯呋喃糖基腺嘌呤环3',5'-磷酸酯和9-β-D-阿拉伯呋喃糖基鸟嘌呤环3',5'-磷酸酯的合成及生物活性
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Studies on neutral esters of cyclic AMP.环磷酸腺苷中性酯的研究
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Activity of tubercidin-, toyocomycin-, and sangivamycin-3',5'-cyclic phosphates and related compounds with some enzymes of adenosine-3',5'-cyclic phosphate metabolism.
Biochem Biophys Res Commun. 1973 Dec 10;55(3):843-9. doi: 10.1016/0006-291x(73)91221-7.
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Synthesis and biological activity of some purine 5'-thio-5'-deoxynucleoside 3',5'-cyclic phosphorothioates.
Biochemistry. 1973 Jul 17;12(15):2781-6. doi: 10.1021/bi00739a001.
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Synthesis and biological activity of several 6-substituted 9- -D-ribofuranosylpurine 3',5',-cyclic phosphates.
Biochemistry. 1972 Jul 4;11(14):2704-9. doi: 10.1021/bi00764a024.
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5'-amido analogs of adenosine 3',5'-cyclic monophosphate.
J Org Chem. 1971 Oct 8;36(20):3029-33. doi: 10.1021/jo00819a027.
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Chemical synthesis and biological activity of 8-substituted adenosine 3',5'-cyclic monophosphate derivatives.8-取代的3',5'-环磷酸腺苷衍生物的化学合成及生物活性
Biochemistry. 1971 Jun 8;10(12):2390-5. doi: 10.1021/bi00788a033.

七元环磷酸酯：S-环腺苷2',5'-环磷酸酯和虫草素2',5'-环磷酸酯的合成与性质。核苷与核苷酸研究。LXIV。1）. 嘌呤环核苷25。

Seven-membered cyclic phosphate: synthesis and properties of S-cycloadenosine 2',5'-cyclic phosphate and cordycepin 2',5'-cyclic phosphate. Studies of nucleosides and nucleotides. LXIV. 1). Purine cyclonucleosides 25.

作者信息

Ikehara M, Yano J

出版信息

Nucleic Acids Res. 1974 Dec;1(12):1783-98. doi: 10.1093/nar/1.12.1783.

DOI:10.1093/nar/1.12.1783
PMID:4375806
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC343457/
Abstract

8,3'-Anhydro-8-mercapto-9-beta-D-xylofuranosyladenine (8,3'-s-cycloadenosine) was phosphorylated with cyanoethyl phosphate and DCC to 5'-phosphate. After 6-amino group was benzoylated, the monophosphate was treated with DCC to give a cyclic phosphate (II). The structure of compound II was elucidated as 8,3'-s-cycloadenosine 2',5'-cyclic phosphate by UV, NMR and CD spectra, as well as enzymatic hydrolyses. When compound II was desulfurized with Raney nickel, cordycepin 2',5'-cyclic phosphate (III) was obtained. Although compound III could be obtained from cordycepin 5'-phosphate with DCC, the yield was extremely low.

摘要

8,3'-脱水-8-巯基-9-β-D-木糖呋喃糖基腺嘌呤（8,3'-s-环腺苷）用氰乙磷酸和二环己基碳二亚胺（DCC）磷酸化生成5'-磷酸酯。6-氨基进行苯甲酰化后，单磷酸酯用DCC处理得到环状磷酸酯（II）。通过紫外光谱、核磁共振光谱和圆二色光谱以及酶促水解确定化合物II的结构为8,3'-s-环腺苷2',5'-环磷酸酯。当用雷尼镍对化合物II进行脱硫时，得到虫草素2',5'-环磷酸酯（III）。虽然化合物III可以由虫草素5'-磷酸酯与DCC反应得到，但产率极低。