heal.abstract |
Synthetic carbobenzoxy-β-benzyl-L-aspartyl-L-serylglycine benzyl ester and carbobenzoxy-β-benzyl-L-aspartyl-L-seryl-L-glutamic dibenzyl ester were phosphorylated by means of di-p-nitrobenzylphosphorochloridate in the presence of imidazole in 90% and 50% yield, respectively. The crude phosphate triesters, carbobenzoxy-β-benzyl-L-aspartyl-O-(O,O-di-p-nitrobenzylphospho)-L- serylglycine benzyl ester and carbobenzoxy-β-benzyl-L-aspartyl-O-(O,O-di-p-nitrobenzylphospho)-L-seryl-L- glutamic dibenzyl ester could not be purified by fractional precipitation from usual solvents; however, countercurrent distribution has been found to be a suitable technique for isolating these and related substances in analytically pure form Preliminary experiments on the synthesis of phosphodiesters of serine are also described. In this connection, O-butylphospho-D,L-serine was synthesized and its isolation from by-products, e.g., phosphoserine and serine, was effected by countercurrent distribution. |
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