320727-46-6

Upstream product

• 14533-84-7 pentafluorophenyl trifloroacetate 
• 664966-99-8 [(2R,4R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidin-1-yl]-acetic acid 
• 320727-41-1 N-(tert-butoxycarbonyl)-(2'R,4'R)-2'-[(phthalimido)methyl]-4'-(thymin-1-yl)pyrrolidine 
• 320727-38-6 cis-4'-(N³-benzoylthymin-1-yl)-N-(tert-butoxycarbonyl)-D-proline ethyl ester 
• 320727-44-4 2-[(2R,4R)-4-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidin-2-ylmethyl]-isoindole-1,3-dione 
• 320727-40-0 N-(tert-butoxycarbonyl)-cis-4'-(thymin-1-yl)-D-prolinol 
• 136918-14-4 phthalimide 
• 320727-45-5 (2'R,4'R)-N-[(tert-butoxycarbonyl)methyl]-2'-[(phthalimido)methyl]-4'-(thymin-1-yl)pyrrolidine 

Downstream Products

• 664967-03-7 2-({2-[2-[(2-methylcarbamoyl-benzoylamino)-methyl]-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidin-1-yl]-acetylamino}-methyl)-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Unusual RNA and DNA binding properties of a novel pyrrolidine-amide oligonucleotide mimic (POM)

A pentameric thymidyl pyrrolidine-amide oligonucleotide mimic (POM) was synthesised and shown to bind with very high affinity to complementary single stranded RNA and DNA, whilst exhibiting kinetic binding selectivity for RNA over DNA.

Design, synthesis, conformational analysis and nucleic acid hybridisation properties of thymidyl pyrrolidine-amide oligonucleotide mimics (POM)

Pyrrolidine-amide oligonucleotide mimics (POM) 1 were designed to be stereochemically and conformationally similar to natural nucleic acids, but with an oppositely charged, cationic backbone. Molecular modelling reveals that the lowest energy conformation of a thymidyl-POM monomer is similar to the conformation adopted by ribonucleosides. An efficient solution phase synthesis of the thymidyl POM oligomers has been developed, using both N-alkylation and acylation coupling strategies. 1H NMR spectroscopy confirmed that the highly water soluble thymidyl-dimer, T2-POM, preferentially adopts both a configuration about the pyrrolidine N-atom and an overall conformation in D2O that are very similar to a typical C3′-endo nucleotide in RNA. In addition the nucleic acid hybridisation properties of a thymidyl-pentamer, T5-POM, with an N-terminal phthalimide group were evaluated using both UV spectroscopy and surface plasmon resonance (SPR). It was found that T5-POM exhibits very high affinity for complementary ssDNA and RNA, similar to that of a T 5-PNA oligomer. SPR experiments also showed that T5-POM binds with high sequence fidelity to ssDNA under near physiological conditions. In addition, it was found possible to attenuate the binding affinity of T 5-POM to ssDNA and RNA by varying both the ionic strength and pH. However, the most striking feature exhibited by T5-POM is an unprecedented kinetic binding selectivity for ssRNA over DNA.