Synthesis of an ethidium nucleoside and its acyclic analog

Synthesis of an ethidium nucleoside and its acyclic analog
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DOI:
10.1016/s0040-4039(03)00025-x
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发表时间:
2003-02-17
影响因子:
1.8
通讯作者:
Wagenknecht, HA
Wagenknecht, HA
中科院分区:
化学4区
文献类型:
--
作者:
Amann, N;Wagenknecht, HA

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保护的乙锭核苷8-(3 ',5'-二-O-苯甲酰基-2 '-脱氧-D-呋喃核糖基)-3-乙酰氨基-5-乙基-6-苯基菲啶鎓(5),8-(3 ′,5 ′-二-O-乙酰基-2 ′-脱氧-D-呋喃核糖基)-3-乙酰氨基-5-乙基-6-苯基-菲啶鎓(6),和无环类似物8-[(3R)-1,合成了3-二羟基-4-基]-乙酰氨基-3-氨基-5-乙基-6-苯基菲啶鎓(3)。基于它们不同的稳定性,只有无环衍生物3似乎适合于寡核苷酸合成。此外,无环乙锭核苷类似物3表现出与未衍生化乙锭(1)相当的吸收和发射性质。(C)2003爱思唯尔科技有限公司版权所有。
The protected ethidium nucleosides 8-(3',5'-di-O-benzoyl-2'-deoxy-D-ribofuranosyl)-3-acetamido-5-ethyl-6-phenylphenanthridinium (5), 8-(3',5'-di-O-acetyl-2'-deoxy-D-ribofuranosyl)-3-acetamido-5-ethyl-6-phenyl-phenanthridinium (6), and the acyclic analog 8-[(3R)-1,3-dihydroxy-4-yl]-acetamido-3-amino-5-ethyl-6-phenyl-phenanthridinium (3) were prepared. Based on to their different stability, only the acyclic derivative 3 seems to be suitable for oligonucleotide synthesis. Furthermore, the acyclic ethidium nucleoside analog 3 exhibits comparable absorption and emission properties of the underivatized ethidium (1). (C) 2003 Elsevier Science Ltd. All rights reserved.