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N-(鸟苷-8-基)-4-氨基联苯及其5'-单磷酸酯的新合成方法。

New syntheses of N-(guanosin-8-yl)-4-aminobiphenyl and its 5'-monophosphate.

作者信息

Lee M S, King C M

出版信息

Chem Biol Interact. 1981 Mar 1;34(2):239-48. doi: 10.1016/0009-2797(81)90135-6.

DOI:10.1016/0009-2797(81)90135-6
PMID:6257408
Abstract

N-Acetoxy-4-trifluoroacetylaminobiphenyl (N-acetoxy-TFAABP) reacted readily with Guo and GMP at neutrality in a one-step fashion to yield N-(guanosin-8-yl)4-aminobiphenyl (Guo-ABP) (I) and N(guanosin-8-yl)-4-aminobiphenyl-5'-monophosphate (GMP-ABP) (II), respectively. GMP-ABP could also be formed in much lower yield from the reaction of N-acetoxy-4-formylaminobiphenyl (N-acetoxy-FABP) with GMP (pH 7.0) under more rigorous conditions. Enzymatic hydrolysis of GMP-ABP with alkaline phosphatase in Tris buffer (pH 8.0) at 37 degrees C yielded Guo-ABP. Guo-ABP showed a brilliant blue fluorescence on exposure to 366 nm UV light and its UV absorption spectrum was identical to that of Guo-ABP prepared by Kriek via a different route. Elemental analysis and nuclear magnetic resonance (NMR) data further confirmed the identity of this compound.

摘要

N-乙酰氧基-4-三氟乙酰氨基联苯(N-乙酰氧基-TFAABP)在中性条件下能与鸟苷(Guo)和鸟苷-5'-单磷酸(GMP)一步反应,分别生成N-(鸟苷-8-基)-4-氨基联苯(Guo-ABP)(I)和N-(鸟苷-8-基)-4-氨基联苯-5'-单磷酸(GMP-ABP)(II)。在更严格的条件下,N-乙酰氧基-4-甲酰氨基联苯(N-乙酰氧基-FABP)与GMP(pH 7.0)反应也能生成产率低得多的GMP-ABP。在37℃下,于Tris缓冲液(pH 8.0)中用碱性磷酸酶对GMP-ABP进行酶促水解,生成Guo-ABP。Guo-ABP在366nm紫外光照射下呈现亮蓝色荧光,其紫外吸收光谱与Kriek通过不同途径制备的Guo-ABP相同。元素分析和核磁共振(NMR)数据进一步证实了该化合物的结构。

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引用本文的文献

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