64987-77-5Relevant academic research and scientific papers
(±)-cis-4a-alkyl-1,3,4,4a,9,9a-hexahydro-2H-carbazol-2-ones by domino nitro reduction-aza-Michael addition to enones
Barrios-Perez, Carlos,Bunce, Richard A.,Embrey, Samuel J.
, (2022/01/11)
A domino nitro reduction-aza-Michael addition sequence has been investigated for α,β-unsaturated ketones and compared with the analogous reaction for conjugated esters. As expected, six-membered ring closures of ketones did not proceed as well as for esters (85%) due to the greater inherent reactivity of the ketones. This problem was minimized by performing the cyclization at lower temperature for a shorter time. The process has been extended to a synthesis of (±)-cis-4a-alkyl-1,3,4,4a,9,9a-hexahydro-2H-carbazol-2-ones with good yields (65%–86%). While the rigidity of the system and closure of the smaller five-membered ring created some strain in the products, yields were acceptable. The cis ring junction resulted from axial attack to give a more stable chair-like enol that tautomerized to the target heterocycle.
A Singular System with Precise Dosing and Spatiotemporal Control of CRISPR-Cas9
Manna, Debasish,Maji, Basudeb,Gangopadhyay, Soumyashree A.,Cox, Kurt J.,Zhou, Qingxuan,Law, Benjamin K.,Mazitschek, Ralph,Choudhary, Amit
supporting information, p. 6285 - 6289 (2019/04/08)
Several genome engineering applications of CRISPR-Cas9, an RNA-guided DNA endonuclease, require precision control of Cas9 activity over dosage, timing, and targeted site in an organism. While some control of Cas9 activity over dose and time have been achieved using small molecules, and spatial control using light, no singular system with control over all the three attributes exists. Furthermore, the reported small-molecule systems lack wide dynamic range, have background activity in the absence of the small-molecule controller, and are not biologically inert, while the optogenetic systems require prolonged exposure to high-intensity light. We previously reported a small-molecule-controlled Cas9 system with some dosage and temporal control. By photocaging this Cas9 activator to render it biologically inert and photoactivatable, and employing next-generation protein engineering approaches, we have built a system with a wide dynamic range, low background, and fast photoactivation using a low-intensity light while rendering the small-molecule activator biologically inert. We anticipate these precision controls will propel the development of practical applications of Cas9.
Photoresponsive cross-linked polymeric particles for phototriggered burst release
Wang, Zhen,Yu, Lili,Lv, Cong,Wang, Peng,Chen, Yedong,Tang, Xinjing
, p. 552 - 559 (2013/06/26)
We synthesized a series of cross-linked photoresponsive polymeric particles with photolabile monomers and cross-linkers through miniemulsion polymerization. These particles are quite stable in dark, while light irradiation caused the breakage of particles and the efficient release of encapsulated contents up to 95% based on Nile red fluorescence. Photoswitches of particle systems were confirmed by fluorescence spectroscopy, SEM and colorimetry. Particle uptake and triggered release in RAW264.7 cells were confirmed by fluorescein diacetate loaded particles.
Caged glutathione - Triggering protein interaction by light
Gatterdam, Volker,Stoess, Tatjana,Menge, Clara,Heckel, Alexander,Tampe, Robert
supporting information; experimental part, p. 3960 - 3963 (2012/06/15)
Light, GSH, action! Glutathione (GSH) fulfills a universal role as redox factor, scavenger of reactive oxygen species, and as an essential substrate in the conjugation, detoxification, and reduction reactions catalyzed by glutathione S-transferase (GST). A photoactivatable glutathione allows the GSH-GST network to be triggered by light. GST fusion proteins can be assembled in situ at variable density and structures by laser-scanning activation. Copyright
Lipase-mediated resolution of substituted 2-aryl-propanols: Application to the enantioselective synthesis of phenolic sesquiterpenes
Serra, Stefano
, p. 619 - 628 (2011/07/08)
A comprehensive study of the lipase-mediated resolution of substituted 2-aryl-propanols is reported. The latter alcohols were submitted to the irreversible acetylation catalyzed either by PPL, CRL, or lipase PS. The enantioselectivity of these transformations was dependent on the type of lipase used. The type of substituents and particularly their position on the aromatic ring strongly affected the selectivity of the reaction. The experiments described prove that PPL is the more versatile lipase catalyzing the acetylation with an enantiomeric ratio (E) value that ranges from 1 up to 144, depending on the substrate used. Conversely, the same transformations were catalyzed by CRL and lipase PS with an enantiomeric ratio value, which is always less than 5. The remarkable behavior of PPL was exploited in the large scale resolution of some substituted 2-aryl-propanols whose enantiomeric forms are relevant building blocks in the enantioselective synthesis of phenolic sesquiterpenes. By these means, the synthesis of (S)-turmeronol B and the formal syntheses of (R)-curcumene, (R)-curcuphenol, (R)-xanthorrhizol, and (R)-curcuhydroquinone were accomplished.
METHOD FOR PREPARING DNA FRAGMENT HAVING STICKY END
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, (2011/02/15)
The present invention provides a method for preparing a DNA fragment, in which a desired double-stranded DNA fragment having a sticky end is directly and easily obtained from an amplification product (an amplified fragment) after PCR without a restriction
Micrometer-and nanometer-scale photopatterning using 2- nitrophenylpropyloxycarbonyl-protected aminosiloxane monolayers
Alang Ahmad, Shahrul A.,Wong, Lu Shin,ul-Haq, Ehtsham,Hobbs, Jamie K.,Leggett, Graham J.,Micklefield, Jason
experimental part, p. 1513 - 1522 (2009/07/30)
An approach to nanopatterning is reported in which a scanning near-fieldoptical microscope coupled to a near-UV laser is used to selectively de protect 2-nitrophenylpropyloxycarbonyl (NPPOC)-protected aminosiloxane monolayers on glass. UV deprotection was
Synthesis of a photo-caged aminooxy alkane thiol
Mancini, Rock J.,Li, Ronald C.,Tolstyka, Zachary P.,Maynard, Heather D.
experimental part, p. 4954 - 4959 (2010/02/16)
A photo-caged aminooxy alkane thiol synthesized in 7 steps and 15% overall yield was used to form a self-assembled monolayer (SAM). Photo-deprotection on the surface was confirmed by FT-IR spectroscopy and contact angle goniometry. Conjugation of a small molecule ketone, ethyl levulinate, further confirmed the presence of aminooxy groups on the surface. The Royal Society of Chemistry 2009.
Photolabile peptide nucleic acid monomers: Synthesis and photodeprotection
Bhushan, Kumar R.
, p. 2130 - 2132 (2008/02/05)
The photolabile 2-(2-nitrophenyl)propyloxy carbonyl (NPPOC) group has been introduced as an amino protecting group for peptide nucleic acids (PNA) to be used as building blocks in photolithographic solid-phase PNA synthesis. NPPOC-protected PNA derivative
Photogenerated reagents
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Page/Page column 16-17, (2008/06/13)
This invention describes reagent precursors and methods for chemical and biochemical reactions. These reagent precursors that can be activated in solution upon irradiation to generate reagents required for the subsequent chemical reactions. Specifically, photogenerated reagents (PGR) are useful for controlling parallel combinatorial synthesis and various chemical and biochemical reactions.
