碱基修饰的2'-脱氧肌苷类似物的亚磷酰胺酯及含模糊碱基的d(GCI*CGC)寡聚物的固相合成
Phosphoramidites of base-modified 2'-deoxyinosine isosteres and solid-phase synthesis of d(GCI*CGC) oligomers containing an ambiguous base.
作者信息
Seela F, Kaiser K
出版信息
Nucleic Acids Res. 1986 Feb 25;14(4):1825-44. doi: 10.1093/nar/14.4.1825.
Abstract
Novel phosphoramidites (1,2) of appropriately protected 2'-deoxyinosine isosteres (I*) such as allopurinol 2'-deoxyribofuranoside (4a) and 7-deaza-2'-deoxyinosine (4b) have been synthesized. They were employed together with the phosphoramidite of 2'-deoxyinosine in solid-phase synthesis of d(GCI*CGC) hexamers (12a-d). From thermodynamic data of these alternating hexamers it was shown that allopurinol 2'-deoxyribofuranoside destabilizes such duplexes less strongly than 2'-deoxyinosine. Additionally, the phosphoramidite of 7-deaza-2'-deoxyinosine (2) exhibits an extraordinary stability of the N-glycosylic bond. Since the new phosphoramidites are structurally related to 2'-deoxyinosine, they can be used in the construction of hybridization probes containing an ambiguous base.
摘要
已合成了适当保护的2'-脱氧肌苷类似物（I*）的新型亚磷酰胺酯（1,2），如别嘌呤醇2'-脱氧呋喃核糖苷（4a）和7-脱氮-2'-脱氧肌苷（4b）。它们与2'-脱氧肌苷的亚磷酰胺酯一起用于固相合成d(GCI*CGC)六聚体（12a-d）。从这些交替六聚体的热力学数据表明，别嘌呤醇2'-脱氧呋喃核糖苷使此类双链体不稳定的程度比2'-脱氧肌苷弱。此外，7-脱氮-2'-脱氧肌苷的亚磷酰胺酯（2）表现出N-糖苷键的非凡稳定性。由于新的亚磷酰胺酯在结构上与2'-脱氧肌苷相关，它们可用于构建含有模糊碱基的杂交探针。
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本文引用的文献
1
An investigation by 1H NMR spectroscopy into the factors determining the beta:alpha ratio of the product in 2'-deoxynucleoside synthesis.通过¹H核磁共振光谱法对2'-脱氧核苷合成中决定产物β:α比例的因素进行的一项研究。
Nucleic Acids Res. 1984 Sep 11;12(17):6827-37. doi: 10.1093/nar/12.17.6827.
2
Sequence dependence of conformations of self-complementary duplex tetradeoxynucleotides containing cytosine and guanine.
Biochemistry. 1984 Jul 3;23(14):3202-7. doi: 10.1021/bi00309a014.
3
Thermodynamics of (dG--dC)3 double-helix formation in water and deuterium oxide.水中及氧化氘中(dG--dC)3双螺旋形成的热力学
Biochemistry. 1981 Mar 17;20(6):1409-13. doi: 10.1021/bi00509a001.
4
Use of synthetic oligonucleotides as hybridization probes: isolation of cloned cDNA sequences for human beta 2-microglobulin.合成寡核苷酸作为杂交探针的应用：人β2-微球蛋白克隆cDNA序列的分离
Proc Natl Acad Sci U S A. 1981 Nov;78(11):6613-7. doi: 10.1073/pnas.78.11.6613.
5
Codon--anticodon pairing: the wobble hypothesis.密码子-反密码子配对：摆动假说
J Mol Biol. 1966 Aug;19(2):548-55. doi: 10.1016/s0022-2836(66)80022-0.
6
Physicochemical studies on polydeoxyribonucleotides containing defined repeating nucleotide sequences.对含有特定重复核苷酸序列的聚脱氧核糖核苷酸的物理化学研究。
J Mol Biol. 1970 Dec 28;54(3):465-97. doi: 10.1016/0022-2836(70)90121-x.
7
Synthesis of 5-S-substituted 2'-deoxyuridines. Study of the factors influencing stereoselectivity of the silyl modification of the Hilbert-Johnson reaction.5-S-取代-2'-脱氧尿苷的合成。影响希尔伯特-约翰逊反应硅烷化修饰立体选择性因素的研究。
J Org Chem. 1969 Dec;34(12):3806-13. doi: 10.1021/jo01264a015.
8
Free energy of imperfect nucleic acid helices. II. Small hairpin loops.不完全核酸螺旋的自由能。II. 小发夹环
J Mol Biol. 1973 Feb 5;73(4):497-511. doi: 10.1016/0022-2836(73)90096-x.
9
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Eur J Biochem. 1974 Mar 1;42(2):495-504. doi: 10.1111/j.1432-1033.1974.tb03364.x.
10
Stability of ribonucleic acid double-stranded helices.核糖核酸双链螺旋的稳定性
J Mol Biol. 1974 Jul 15;86(4):843-53. doi: 10.1016/0022-2836(74)90357-x.
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