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.
Xiang, Zheng,Wang, Lei
p. 6367 - 6371
(2011/10/02)
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