Acid‐Stable Nucleobase Protection for a Strongly Pairing Pyridone C‐Nucleoside Suitable for Solid‐Phase Synthesis of Oligonucleotides

نویسندگان

چکیده

Oligonucleotides are indispensable tools in diagnostics, therapeutic applications and molecular biology. The low base pairing strength of thymine with adenine complicates their use. Ethynylpyridone C -nucleoside analogs thymidine that pair more strongly improved selectivity, sequences containing these show target affinity but routine use is hampered by diminished yields solid-phase syntheses the known building blocks. A partial loss protecting groups during acidic deblocking step chain extension cycles was identified as cause lower yields. Here we report synthesis an phosphoramidite block featuring a pivaloyloxymethyl (POM) group. This gives oligonucleotides ethynylmethylpyridone high yield purity via solid phase synthesis.

برای دانلود باید عضویت طلایی داشته باشید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Polymerase synthesis of oligonucleotides containing a single chemically modified nucleobase for site-specific redox labelling.

Enzymatic construction of single-nucleobase redox-labelled oligonucleotides was developed either based on polymerase incorporation of a single modified nucleoside triphosphate (dNTP) followed by primer extension (PEX) with natural dNTPs or based on PEX with a biotinylated one-nucleotide overhang template, magnetoseparation and the second PEX with a full-length template.

متن کامل

investigating the feasibility of a proposed model for geometric design of deployable arch structures

deployable scissor type structures are composed of the so-called scissor-like elements (sles), which are connected to each other at an intermediate point through a pivotal connection and allow them to be folded into a compact bundle for storage or transport. several sles are connected to each other in order to form units with regular polygonal plan views. the sides and radii of the polygons are...

Nucleobase analogs for degenerate hybridization devised through conformational pairing analysis.

A conformational pairing analysis was used to devise nucleobase analogs capable of forming nonselective and energetically favorable base pairs opposite either the purine or the pyrimidine constituents of nucleic acids. 5-methylisocytosine and isoguanine were conceived as a degenerate pyrimidine and a degenerate purine, respectively. Data from previous DNA duplex melting experiments verified tha...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

ژورنال

عنوان ژورنال: European Journal of Organic Chemistry

سال: 2022

ISSN: ['1434-193X', '1099-0690']

DOI: https://doi.org/10.1002/ejoc.202200611