Studies on Cyclic Dipeptides. II. Isomerization among <I>cyclo</I>(-4-Hydroxyprolyl-4-hydroxyprolyl-)s and a Novel Conversion of D-<I>allo</I>-Hydroxyproline to L-Hydroxyproline

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概要

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• The isomerization among <I>c</I>-L-Hyp-L-Hyp (<B>1</B>), <I>c</I>-L-Hyp-D-<I>a</I>Hyp (<B>2</B>) and <I>c</I>-D-<I>a</I>Hyp-D-<I>a</I>Hyp (<B>3</B>) has been examined in ethanolic sodium ethoxide at 25–78 °C as well as in aqueous solutions at 75–250 °C. At equilibrium state, <B>1</B> was predominant and <B>2</B> was not found at all in the reaction mixture. By the use of this isomerization reaction and the difference of solubility between <B>1</B> and <B>3</B>, <B>3</B> could be converted almost quantitatively to <B>1</B>. The mixture of <B>1</B> and <B>3</B> was obtained in good yield directly from D-<I>a</I>Hyp or L-Hyp by heating in water or ethylene glycol. <B>1</B> was hydrolyzed quantitatively to L-Hyp by acid. Thus, L-Hyp was obtained with the yield of 59% from D-<I>a</I>Hyp by combination of preparation, isomerization and acid hydrolysis of cyclic dipeptide.

• 公益社団法人 日本化学会の論文

著者

• Eguchi Chikahiko

  Central Research Laboratories Ajinomoto Co. Jnc.

• Kakuta Akio

  Central Research Laboratories, Ajinomoto Co., Inc.

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