A convenient and highly efficient synthesis of one kind of peptide nucleic acid monomer

oleh: Xuemei Tang, Guangxia Tang, Hang Wang, Lingfei Luo, Dacheng Yang

Format: Article
Diterbitkan: Chemical Society of Ethiopia 2012-12-01

Deskripsi

<i>S</i>-Thyminyl-<i>L</i>-cysteine methyl ester hydrochloride (compound 1), a non-classical peptide nucleic acid monomer, was synthesized through the key intermediate, <i>N-tert</i>- butoxycarbonyl-<i>S</i>-thyminyl-<i>L</i>-cysteine (compound 3), which afforded from the reaction of <i>S</i>-thyminyl-<i>L</i>-cysteine hydrochloride (compound 2) with di-<i>tert</i>-butyl dicarbonate (Boc<sub>2</sub>O). This was followed by the esterification and deprotection of compound 3 at an overall yield of 82%. The mixture of thionyl chloride and methanol was found as an efficient reagent for simultaneous deprotection of <i>tert</i>-butoxycarbonyl (Boc) group and esterification of carboxy group of compound 3. This high-yield two-step method was also applied to other analogues of compound 1 successfully. The chemical structures of four new compounds (5a-5d) were confirmed by <sup>1</sup>H NMR and <sup>13</sup>C NMR.DOI: http://dx.doi.org/10.4314/bcse.v26i3.10