用于三聚体寡脱氧核糖核苷酸3´-(2-氯苯基磷酸酯)结构单元溶液相合成的二硫键连接的沉淀性可溶性载体的制备。
Preparation of a disulfide-linked precipitative soluble support for solution-phase synthesis of trimeric oligodeoxyribonucleotide 3´-(2-chlorophenylphosphate) building blocks.
作者信息
Jabgunde Amit M, Molina Alejandro Gimenez, Virta Pasi, Lönnberg Harri
机构信息
Department of Chemistry, University of Turku, FIN-20014 Turku, Finland ; current address: Rega Institute for Medical Research, Minderbroedersstraat 10, KU Leuven, 3000- Leuven, Belgium.
Department of Chemistry, University of Turku, FIN-20014 Turku, Finland.
出版信息
Beilstein J Org Chem. 2015 Sep 7;11:1553-60. doi: 10.3762/bjoc.11.171. eCollection 2015.
The preparation of a disulfide-tethered precipitative soluble support and its use for solution-phase synthesis of trimeric oligodeoxyribonucleotide 3´-(2-chlorophenylphosphate) building blocks is described. To obtain the building blocks, N-acyl protected 2´-deoxy-5´-O-(4,4´-dimethoxytrityl)ribonucleosides were phosphorylated with bis(benzotriazol-1-yl) 2-chlorophenyl phosphate. The "outdated" phosphotriester strategy, based on coupling of P(V) building blocks in conjunction with quantitative precipitation of the oligodeoxyribonucleotide with MeOH is applied. Subsequent release of the resulting phosphate and base-protected oligodeoxyribonucleotide trimer 3'-pTpdC(Bz)pdG(ibu)-5' as its 3'-(2-chlorophenyl phosphate) was achieved by reductive cleavage of the disulfide bond.
本文描述了一种二硫键连接的沉淀性可溶载体的制备及其在三聚体寡聚脱氧核糖核苷酸3´-(2-氯苯基磷酸酯)结构单元的溶液相合成中的应用。为了获得这些结构单元，用双(苯并三唑-1-基)2-氯苯基磷酸酯对N-酰基保护的2´-脱氧-5´-O-(4,4´-二甲氧基三苯甲基)核糖核苷进行磷酸化。采用了基于P(V)结构单元偶联并结合用甲醇对寡聚脱氧核糖核苷酸进行定量沉淀的“过时”的磷酸三酯策略。通过二硫键的还原裂解，随后得到了磷酸和碱基保护的寡聚脱氧核糖核苷酸三聚体3'-pTpdC(Bz)pdG(ibu)-5'，其形式为3'-(2-氯苯基磷酸酯)。
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