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首页> 外文期刊>RSC Advances >P-stereocontrolled synthesis of oligo(nucleoside N3 '-> O5 ' phosphoramidothioate)s - opportunities and limitations
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P-stereocontrolled synthesis of oligo(nucleoside N3 '-> O5 ' phosphoramidothioate)s - opportunities and limitations

机译：寡核苷酸（核苷N3' - > O5'磷酰胺类酸的合成合成） - 机遇与限制

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摘要

3 '-N-(2-Thio-1,3,2-oxathiaphospholane) derivatives of 5 '-O-DMT-3 '-amino-2 ',3 '-dideoxy-ribonucleosides (NOTP-N), that bear a 4,4-unsubstituted, 4,4-dimethyl, or 4,4-pentamethylene substituted oxathiaphospholane ring, were synthesized. Within these three series,NOTP-N differed by canonical nucleobases (i.e., Ade(Bz), Cyt(Bz), Gua(iBu), or Thy). The monomers were chromatographically separated into P-diastereomers, which were further used to prepare NNPSN ' dinucleotides (3), as well as short P-stereodefined oligo(deoxyribonucleoside N3 '-> O5 ' phosphoramidothioate)s (NPS-) and chimeric NPS/PO- and NPS/PS-oligomers. The condensation reaction for(N)OTP-N monomers was found to be 5-6 times slower than the analogous OTP derivatives. When the 5 '-end nucleoside of a growing oligomer adopts a C3 '-endoconformation, a conformational 'clash' with the incoming(N)OTP-N monomer takes place, which is a main factor decreasing the repetitive yield of chain elongation. Although both isomers of NNPSN ' were digested by the HINT1 phosphoramidase enzyme, the isomers hydrolyzed at a faster rate were tentatively assigned theR(P)absolute configuration. This assignment is supported by X-ray analysis of the protected dinucleotide(DMT)dG(NPSMe)(iBu)T(OAc), which is P-stereoequivalent to the hydrolyzed faster P-diastereomer of dG(NPS)T.
机译：3'-N-（2-THIO-1,3,2-恶病静脉膦）衍生物为5'-DMT-3'-amino-2'，3'-德烷氧基核糖核苷（NOTP-N），具有a合成4,4-未取代的，4,4-二甲基或4,4-五亚甲基取代的恶性膦醇环。在这三个系列内，NotP-N由规范核碱基（即，Ade（BZ），Cyt（BZ），GUA（IBU）或Thy）不同。将单体进行色谱分离成P-DIA对映异构体，其进一步用于制备NNPSN的二核苷酸（3），以及短的p-立体缩合寡核苷酸（脱氧核糖核苷N3' - > O 5'磷酰胺酰基）（NPS-）和嵌合NPS / po-和nps / ps-低聚物。 （N）otp-N单体的缩合反应被发现比类似于类似OTP衍生物的5-6倍。当5' - 延长寡聚体的核苷共采用C3'-EndOconformation时，发生具有进入（n）otp-n单体的构象的“冲突”，这是降低链伸长率的重复产率的主要因素。虽然NNPSN的两种异构体“是由HINT1 phosphoramidase酶消化，以更快的速率水解的异构体暂时分配THER（P）绝对构型。受保护的二核苷酸（DMT）DG（NPSME）（IBU）T（IBU）T（OAC）的X射线分析支持该任务，其是DG（NPS）T的水解更快的p-DiapereROMER的p-sereoe等等效。

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  • 来源
    《RSC Advances》 |2020年第58期|共13页
  • 作者

    Radzikowska Ewa; Kaczmarek Renata; Korczynski Dariusz; Krakowiak Agnieszka; Mikolajczyk Barbara; Baraniak Janina; Guga Piotr; Wheeler Kraig A.; Pawlak Tomasz; Nawrot Barbara;

  • 作者单位

    Polish Acad Sci Ctr Mol &

    Macromol Studies Sienkiewicza 112 I-90363 Lodz Italy;

    Polish Acad Sci Ctr Mol &

    Macromol Studies Sienkiewicza 112 I-90363 Lodz Italy;

    Polish Acad Sci Ctr Mol &

    Macromol Studies Sienkiewicza 112 I-90363 Lodz Italy;

    Polish Acad Sci Ctr Mol &

    Macromol Studies Sienkiewicza 112 I-90363 Lodz Italy;

    Polish Acad Sci Ctr Mol &

    Macromol Studies Sienkiewicza 112 I-90363 Lodz Italy;

    Polish Acad Sci Ctr Mol &

    Macromol Studies Sienkiewicza 112 I-90363 Lodz Italy;

    Polish Acad Sci Ctr Mol &

    Macromol Studies Sienkiewicza 112 I-90363 Lodz Italy;

    Whitworth Univ Dept Chem 300 W Hawthorne Rd Spokane WA 99251 USA;

    Polish Acad Sci Ctr Mol &

    Macromol Studies Sienkiewicza 112 I-90363 Lodz Italy;

    Polish Acad Sci Ctr Mol &

    Macromol Studies Sienkiewicza 112 I-90363 Lodz Italy;

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