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Anomeric inversion (from beta to alpha) in methylphosphonate oligonucleosides enhances their affinity for DNA and RNA.甲基膦酸酯寡核苷中的异头翻转（从β型到α型）增强了它们对DNA和RNA的亲和力。
Nucleic Acids Res. 1998 Oct 15;26(20):4551-6. doi: 10.1093/nar/26.20.4551.
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引用本文的文献

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Cationic phosphoramidate alpha-oligonucleotides efficiently target single-stranded DNA and RNA and inhibit hepatitis C virus IRES-mediated translation.阳离子氨基磷酸酯α-寡核苷酸能有效靶向单链DNA和RNA，并抑制丙型肝炎病毒内部核糖体进入位点介导的翻译。
Nucleic Acids Res. 2003 Sep 15;31(18):5282-90. doi: 10.1093/nar/gkg733.

甲基膦酸酯寡核苷中的异头翻转（从β型到α型）增强了它们对DNA和RNA的亲和力。

Anomeric inversion (from beta to alpha) in methylphosphonate oligonucleosides enhances their affinity for DNA and RNA.

作者信息

Debart F, Meyer A, Vasseur J J, Rayner B

机构信息

Laboratoire de Chimie Bio-organique, CC008, UMR 5625 CNRS-UM II, Université Montpellier II, Place Eugène Bataillon, 34095 Montpellier Cedex 5, France.

出版信息

Nucleic Acids Res. 1998 Oct 15;26(20):4551-6. doi: 10.1093/nar/26.20.4551.

DOI:10.1093/nar/26.20.4551
PMID:9753720
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC147882/
Abstract

Here we report that the poor binding of methylphosphonate oligodeoxynucleosides (MP-ODNs) to their nucleic acid targets can be improved by additional inversion of the anomeric configuration (from beta to alpha) in the sugar moieties to give a new class of analogs, MP alpha-oligonucleosides. MP alpha-dT12and MP 5' alpha-d(TCTTAACCCACA) 3' were synthesized and their ability to form hybrids with complementary single stranded (ss)DNA and ssRNA, as well as with double stranded (ds)DNA, was evaluated. The thermal stability of hybrids formed with MP alpha-analogs was compared with the affinity of phosphodiester (PO) and phosphorothioate (PS) beta- and alpha-oligomers for their targets. Non-ionic MP alpha-oligonucleosides bound to their complementary DNA and RNA strands more tightly than their homologues with natural beta-anomeric configuration did. With DNA target, MP alpha-oligomers formed duplexes more stable than the corresponding natural PO beta-oligomer did. MP alpha-heteropolymer hybridized to RNA target better than PS beta-oligonucleotide did but the hybrid was less stable (DeltaTm-0.5 degrees C per mod.) than the hybrid formed with the natural PO beta-oligomer. Only MP alpha-dT12 bound to dsDNA target at low salt concentration (0.1 M NaCl).

摘要

在此我们报告，通过在糖部分额外将异头构型（从β型转变为α型）进行转化，可以改善甲基膦酸酯寡脱氧核苷（MP - ODNs）与其核酸靶标的结合能力，从而得到一类新型类似物，即MPα - 寡核苷。合成了MPα - dT12和MP 5'α - d(TCTTAACCCACA) 3'，并评估了它们与互补单链（ss）DNA、ssRNA以及双链（ds）DNA形成杂交体的能力。将与MPα - 类似物形成的杂交体的热稳定性与磷酸二酯（PO）和硫代磷酸酯（PS）β - 和α - 寡聚物对其靶标的亲和力进行了比较。非离子型MPα - 寡核苷与其互补的DNA和RNA链的结合比具有天然β - 异头构型的同源物更紧密。对于DNA靶标，MPα - 寡聚物形成的双链体比相应的天然POβ - 寡聚物更稳定。MPα - 杂聚物与RNA靶标的杂交效果比PSβ - 寡核苷酸更好，但该杂交体的稳定性（每摩尔ΔTm为 - 0.5℃）低于与天然POβ - 寡聚物形成的杂交体。只有MPα - dT12在低盐浓度（0.1 M NaCl）下能与dsDNA靶标结合。