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J Org Chem. 2011 Aug 5;76(15):6367-71. doi: 10.1021/jo2007626. Epub 2011 Jul 6.

Enantiospecific synthesis of genetically encodable fluorescent unnatural amino acid L-3-(6-acetylnaphthalen-2-ylamino)-2-aminopropanoic acid.

Author information

  • 1The 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.

Abstract

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.

PMID:
21732687
[PubMed - indexed for MEDLINE]
PMCID:
PMC3155268
Free PMC Article

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