Synthesis of an mRNA fragment of alanyl-tRNA synthetase gene in Escherichia coli using the 6-methyl-3-pyridyl group for protection of the imide functions of uridine and guanosine.

C J Welch, X X Zhou, J Chattopadhyaya
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引用次数: 8

Abstract

The synthesis of 5'-GpGpUpGpU-3' is reported to demonstrate the synthetic use of the 6-methyl-3-pyridyl group for the protection of the O-4 and O-6 imide functions of uridine and guanosine, respectively. The 2'- and 5'-hydroxyl functions of the key intermediates were protected with two acid-labile groups: 3-methoxy-1,5-dicarbomethoxypentane-3-yl (MDMP) and 9-(4-octadecyloxyphenyl)xanthen-9-yl (C18Px), respectively. The internucleotide phosphotriesters were protected with 2-chlorophenyl and the 9-fluorenylmethyl group was employed for 3'-terminal phosphate protection.

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利用6-甲基-3-吡啶基在大肠杆菌中合成丙氨酰trna合成酶基因mRNA片段,保护尿苷和鸟苷的亚胺功能。
5'-GpGpUpGpU-3'的合成证明了6-甲基-3-吡啶基的合成分别保护了尿苷和鸟苷的O-4和O-6亚胺功能。关键中间体的2′-和5′-羟基功能被两个酸不稳定基团分别保护:3-甲氧基-1,5-二甲氧基-氧戊烷-3-基(MDMP)和9-(4-十八烷基氧基)杂原-9-基(C18Px)。核苷酸间磷酸三酯用2-氯苯保护,9-芴基甲基用于3'端磷酸保护。
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