Xue-mei Tang, G. Tang, Hang Wang
Aug 21, 2012
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0
Influential Citations
4
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Journal
Bulletin of The Chemical Society of Ethiopia
Abstract
S -Thyminyl- L -cysteine methyl ester hydrochloride (compound 1 ), a non-classical peptide nucleic acid monomer, was synthesized through the key intermediate, N - tert - butoxycarbonyl- S -thyminyl- L -cysteine (compound 3 ), which afforded from the reaction of S -thyminyl- L -cysteine hydrochloride (compound 2 ) with di- tert -butyl dicarbonate (Boc 2 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 tert -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 1 H NMR and 13 C NMR. KEY WORDS : Thionyl chloride, Esterification, Deprotection, Peptide nucleic acid Bull. Chem. Soc. Ethiop. 2012 , 26(3), 415-420. DOI: http://dx.doi.org/10.4314/bcse.v26i3.10