多核苷酸。XXXI1。密码子第一位含8,2'-S-环腺苷、8,5'-S-环腺苷、8-溴腺苷、8-氧代腺苷和间型霉素的AUG类似物的合成。

Polynucleotides. XXXI1. Synthesis of AUG analogs containing 8,2'-S-cycloadenosine, 8,5'-S-cycloadenosine, 8-bromoadenosin, 8-oxyadenosine and formycin in the first position of the codon.

作者信息

Ikehara M, Nagura T, Otsuka E

出版信息

Nucleic Acids Res. 1975 Aug;2(8):1345-63. doi: 10.1093/nar/2.8.1345.

DOI:10.1093/nar/2.8.1345

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC344386/

Abstract

Five AUG analogs having 8,2'-S-cycloadenosine (I), 8,5'-S-cycloadenosine (II), 8-bromoadenosine (III), 8-oxyadenosine (IV) and formycin (V) in the first position of ApUpG W were synthesized. 3'-Phosphates of I, II and V were synthesized by phosphorylation using cyanoethylphosphate and DCC. In the case of II, 2', 3'-cyclic phosphate was directly obtained. 3'-Phosphates, thus obtained, were properly protected on the 2'-OH and/or the N6-amino group and condensed with U(OBz)pGiBu(iBu)2 using DCC to give ApUpG analogs. Some properties on paper chromatography and electrophoresis, and the UV and CD spectra of these trinucleoside diphosphates are reported.

摘要

合成了在ApUpG W的第一位具有8,2'-S-环腺苷（I）、8,5'-S-环腺苷（II）、8-溴腺苷（III）、8-氧代腺苷（IV）和间型霉素（V）的五种AUG类似物。通过使用氰乙基磷酸酯和二环己基碳二亚胺（DCC）进行磷酸化反应，合成了I、II和V的3'-磷酸酯。对于II，直接得到了2',3'-环磷酸酯。将由此得到的3'-磷酸酯在2'-OH和/或N6-氨基上进行适当保护，然后使用DCC与U(OBz)pGiBu(iBu)2缩合，得到ApUpG类似物。报道了这些三核苷二磷酸在纸色谱和电泳方面的一些性质，以及它们的紫外和圆二色光谱。

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引用本文的文献

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Polynucleotides. XXXII. Further studies on the synthesis of oligonucleotides containing 8,2'-S-cycloadenosine.

Nucleic Acids Res. 1975 Sep;2(9):1539-50. doi: 10.1093/nar/2.9.1539.

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