Improved Synthesis of Pseudoproline and DMB Dipeptide Carboxylic Acids

Synlett Pub Date : 2024-04-15 DOI:10.1055/a-2306-9316
Wyatt C. Powell, Kelly Johnson, Peyton Tran, Ruiheng Jing, Maciej Walczak
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Abstract

We report a mild method for the preparation of Fmoc-protected dipeptides containing a DMB (HMB) group or modified as pseudoprolines. To minimize the loss of the Fmoc protection, we optimized the saponification conditions and included a calcium additive that protected the other base-sensitive functionalities and improved the yield of the free acid (36-82%). The reaction requires a combination of CaCl2 and NaOH in a mixture of i-PrOH and water at room temperature.

Abstract Image

改进伪脯氨酸和 DMB 二肽羧酸的合成
我们报告了一种温和的方法,用于制备含有 DMB (HMB) 基团或修饰为假脯氨酸的 Fmoc 保护二肽。为了尽量减少 Fmoc 保护的损失,我们优化了皂化条件,并加入了一种钙添加剂,以保护其他碱敏感官能团并提高游离酸的产率(36-82%)。反应需要在室温下在 i-PrOH 和水的混合物中加入 CaCl2 和 NaOH。
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