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Enantiospecific Synthesis of Genetically Encodable Fluorescent Unnatural Amino Acid L-3-(6-Acetylnaphthalen-2-ylamino)-2-aminopropanoic Acid.
- Source :
-
Journal of Organic Chemistry . 8/5/2011, Vol. 76 Issue 15, p6366-6371. 6p. - Publication Year :
- 2011
-
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-enantioner 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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *AMINO acids
*PROPANOLAMINES
*PROTEINS
*AMINO compounds
*ORGANIC chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 76
- Issue :
- 15
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 65167330
- Full Text :
- https://doi.org/10.1021/jo2007626