The Jack H. Skirball Center for Chemical Biology and Proteomics, The Salk Institute for Biological Studies, 10010 North Torrey Pines Road, La Jolla, California 92037, USA.
J Org Chem. 2011 Aug 5;76(15):6367-71. doi: 10.1021/jo2007626. Epub 2011 Jul 6.
Fluorescent unnatural amino acids (UAAs), when genetically incorporated into proteins, can provide unique advantages for imaging biological processes in vivo. Synthesis of optically pure L-enantiomer of fluorescent UAAs is crucial for their effective application in live cells. An efficient six-step synthesis of L-3-(6-acetylnaphthalen-2-ylamino)-2-aminopropanoic acid (L-Anap), a genetically encodable and polarity-sensitive fluorescent UAA, has been developed. The synthesis takes advantage of a high-yield and enantiospecific Fukuyama-Mitsunobu reaction as the key transformation.
荧光非天然氨基酸（UAAs）在遗传上整合到蛋白质中时，可以为体内生物过程的成像提供独特的优势。光学纯 L-对映体荧光 UAAs 的合成对于它们在活细胞中的有效应用至关重要。已经开发出一种高效的六步合成 L-3-(6-乙酰基萘-2-基氨基)-2-氨基丙酸（L-Anap）的方法，L-Anap 是一种可遗传的、极性敏感的荧光 UAA。该合成利用高产和对映选择性的 Fukuyama-Mitsunobu 反应作为关键转化。
