酸性α-氨基酸作为酰基供体的应用：芳基酮α-氨基酸及其衍生物的有效立体可控合成。

Utilization of acidic α-amino acids as acyl donors: an effective stereo-controllable synthesis of aryl-keto α-amino acids and their derivatives.

作者信息

Wang Lei, Murai Yuta, Yoshida Takuma, Okamoto Masashi, Tachrim Zetryana Puteri, Hashidoko Yasuyuki, Hashimoto Makoto

机构信息

Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Kita 9, Nishi 9, Kita-ku, Sapporo 060-8589, Japan.

Faculty of Advanced Life Science, Frontier Research Center for Post-Genome Science and Technology, Hokkaido University, Kita 21, Nishi 11, Kita-ku, Sapporo 001-0021, Japan.

出版信息

Molecules. 2014 May 16;19(5):6349-67. doi: 10.3390/molecules19056349.

DOI:10.3390/molecules19056349

PMID:24840903

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6271428/

Abstract

Aryl-keto-containing α-amino acids are of great importance in organic chemistry and biochemistry. They are valuable intermediates for the construction of hydroxyl α-amino acids, nonproteinogenic α-amino acids, as well as other biofunctional components. Friedel-Crafts acylation is an effective method to prepare aryl-keto derivatives. In this review, we summarize the preparation of aryl-keto containing α-amino acids by Friedel-Crafts acylation using acidic α-amino acids as acyl-donors and Lewis acids or Brönsted acids as catalysts.

摘要

含芳基酮的α-氨基酸在有机化学和生物化学中具有重要意义。它们是构建羟基α-氨基酸、非蛋白质ogenicα-氨基酸以及其他生物功能成分的有价值中间体。傅克酰基化是制备芳基酮衍生物的有效方法。在本综述中，我们总结了以酸性α-氨基酸为酰基供体，以路易斯酸或布朗斯特酸为催化剂，通过傅克酰基化反应制备含芳基酮的α-氨基酸的方法。