Synthesis of 3-β-D-Ribofuranosylwye, the Most Probable Structure for Wyosine from Torulopsis utilis Phenylalanine Transfer Ribonucleic Acid
Synthesis of 3-β-D-Ribofuranosylwye, the Most Probable Structure for Wyosine from Torulopsis utilis Phenylalanine Transfer Ribonucleic Acid
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3-β-D-呋喃核糖基wye的合成，这是来自产朊球拟酵母苯丙氨酸转移核糖核酸的最可能的Wyosine结构
DOI：
10.1248/cpb.33.2339
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发表时间：
1985
期刊：
影响因子：
--
通讯作者：
T. Harada
中科院分区：
文献类型：
--
作者：
T. Itaya;H. Matsumoto;Tomoko Watanabe;T. Harada
5-（甲氨基）-1-β- d -核糖呋喃酰基咪唑-4-羧酰胺（5a）在醋酸缓冲液中与CNBr反应得到5-氰氨基衍生物6a，该衍生物在NaOEt存在下环化成3-甲基鸟苷(7)。在K2CO3存在下，7与溴丙酮环缩合得到3-β- d -核糖呋喃基(2)，这是Torulopsis utilis苯丙氨酸转移核糖核酸（tRNAPhe）中最可能的荧光核苷结构。2和7的糖苷键在酸性或碱性条件下都被证明是不寻常的，但在中性条件下被证明是不稳定的，正如已经报道的那样。2的碱基部分在碱性条件下也被裂解。
Treatment of 5-(methylamino)-1-β-D-ribofuranosylimidazole-4-carboxamide (5a) with CNBr in acetate buffer gave the 5-cyanomethylamino derivative 6a, which was cyclized to 3-methyl-guanosine (7) in the presence of NaOEt. Cyclocondensation of 7 with bromoacetone in the presence of K2CO3 provided 3-β-D-ribofuranosylwye (2), the most probable structure for the fluorescent nucleoside from Torulopsis utilis phenylalanine transfer ribonucleic acid (tRNAPhe). The glycosidic bonds of 2 and 7 have been shown to be unusually subject to cleavage under either acidic or basic conditions, but proved to be less labile under neutral conditions, as had been reported. The base moiety of 2 is also cleaved under basic conditions.