320727-38-6

Upstream product

• 77450-02-3 N-(tert-butoxycarbonyl)-trans-4-hydroxy-D-proline ethyl ester 
• 4330-20-5 N-3-benzoylthymine 
• 664967-07-1 N-(tert-butoxycarbonyl)-trans-4-formyloxy-D-proline ethyl ester 

Downstream Products

• 320727-46-6 N-(pentafluorophenyloxycarbonyl)methyl-(2'R,4'R)-2'-[(phthalimido)methyl]-4'-(thymin-1-yl)pyrrolidine 
• 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 
• 664966-95-4 N-(tert-butoxycarbonyl)-cis-4'-(thymin-1-yl)-D-prolinol p-toluenesulfonate 

Relevant academic research and scientific papers

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.