The steric hindrance of the stepwise reaction of N-carboxy .ALPHA.-amino acid anhydride with the .ALPHA.-amino acid ester.
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概要
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The mechanisms of the reactions of 4-alkyloxazolidinediones (<B>1</B>) (<I>N</I>-carboxy α-amino acid anhydrides(NCAs)) with α-amino acid benzyl ester <I>p</I>-toluenesulfonates (<B>2</B>) were investigated in acetonitrile containing triethylamine at low and room temperatures. Two types of reactions were observed: (1) the polymerization of NCAs was initiated with a small amount of <B>2</B> to produce polypeptides (<B>6</B>), and (2) the dipeptide benzyl esters (<B>4</B>) were produced by the stepwise reaction of NCAs with the esters. Both the polymerization and the dipeptide formation (<B>1</B>+<B>2</B>) seemed to be initiated by the nucleophilic attack of the amino group of the ester on the C-5 carbon of NCAs. The polymerization proceeded when the side chains of the amino acid esters (R<SUP>2</SUP>) were more bulky than those of the NCAs (R<SUP>1</SUP>). On the contrary, dipeptide esters were produced when the side chains of the NCAs (R<SUP>1</SUP>) were more bulky than those of the esters (R<SUP>2</SUP>).
- 公益社団法人 日本化学会の論文
著者
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Oya Masanao
Department Of Biochemistry And Engineering Faculty Of Engineering Gunma University
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Takahashi Tomoko
Department Of Cancer Cytogenetics Division Of Molecular Biology Research Institute For Radiation Bio
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Oya Masanao
Department of Chemistry, College of Technology, Gunma University
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- The steric hindrance of the stepwise reaction of N-carboxy .ALPHA.-amino acid anhydride with the .ALPHA.-amino acid ester.