Synthesis and crystal structure of 2-acetylnaphthalen-6-yl 4-methylbenzosulfonate

Li, Jiarong; Zhang, Guang

doi:10.1007/s10870-005-4324-8

J Chem Crystallogr

2005

DOI: 10.1007/s10870-005-4324-8

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Synthesis and crystal structure of 2-acetylnaphthalen-6-yl 4-methylbenzosulfonate

Jiarong Li

Guang Zhang

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Two‐Photon Fluorescent Probes for Long‐Term Imaging of Calcium Waves in Live Tissue

Kim

et al. 2008

Chemistry A European J

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2-Acetyl-6-(dimethylamino)naphthalene-derived two-photon fluorescent Ca2+ probes (ACa1-ACa3) are reported. They can be excited by a 780 nm laser beam, show 23-50-fold enhancement in one- and two-photon excited fluorescence in response to Ca2+, emit fourfold stronger two-photon excited fluorescence than Oregon Green 488 BAPTA-1 upon complexation with Ca2+, and can selectively detect intracellular free Ca2+ ions in live cells and living tissues with minimum interference from other metal ions and membrane-bound probes. Moreover, these probes are capable of monitoring calcium waves at a depth of 120-170 microm in live tissues for 1100-4000 s using two-photon microscopy with no artifacts of photobleaching.

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Two‐Photon Fluorescent Probes for Long‐Term Imaging of Calcium Waves in Live Tissue

Kim

et al. 2008

Chemistry A European J

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Palladium‐catalyzed Substitution of Ketone or Aldehyde Bearing Aryl Triflates by Amines or Amides

et al. 2009

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Various aryl triflates, bearing ketone or aldehyde groups, were evaluated for palladium-mediated introduction of an amino group at the triflate position in the presence of various phosphine ligands. BINAP was best for secondary amines, MOP-type ligand for primary or small secondary amines and Xantphos for primary or cyclic secondary amides. No ligand was found effective for acyclic secondary amides.

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Enantiospecific Synthesis of Genetically Encodable Fluorescent Unnatural Amino Acid l-3-(6-Acetylnaphthalen-2-ylamino)-2-aminopropanoic Acid

Xiang

Wang

2011

J. Org. Chem.

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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.

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Synthesis and crystal structure of 2-acetylnaphthalen-6-yl 4-methylbenzosulfonate

Cited by 3 publications

References 3 publications

Two‐Photon Fluorescent Probes for Long‐Term Imaging of Calcium Waves in Live Tissue

Two‐Photon Fluorescent Probes for Long‐Term Imaging of Calcium Waves in Live Tissue

Palladium‐catalyzed Substitution of Ketone or Aldehyde Bearing Aryl Triflates by Amines or Amides

Enantiospecific Synthesis of Genetically Encodable Fluorescent Unnatural Amino Acid l-3-(6-Acetylnaphthalen-2-ylamino)-2-aminopropanoic Acid

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