Wen Ling
2003
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Journal
Chinese Journal of Medicinal Chemistry
Abstract
Aim To synthesize O acyl or S acyl amino acids by condensation of dicarboxylic acids and amino acids.Methods L serine and L cysteine were protected by Boc,Bn or Dpm,then condensed with succinic monoester,oxalyl monoester to produce the intermediates O (4 benzyloxysuccinyl) N Boc L serine benzyl ester (4), O (2 benzyloxyoxalyl) N Boc L serine benzyl ester (8), N Boc S (4 tert butoxysuccinyl) L cysteine diphenylmethyl ester (12).Compound 4 was converted into O succinnyl N Boc L serine (5)by hydrogenolysis,then into O succinnyl L serine (6) by acidolysis.Results Their structures were confirmed by the spectral detection.Conclusion Dicarboxylic acids can be esterified with OH or SH groups of amino acids by this innovative method.