2446-69-7Relevant academic research and scientific papers
High-Throughput Proteomics Enabled by a Photocleavable Surfactant
Brown, Kyle A.,Eken, Christian,Ge, Ying,Jin, Song,Knott, Samantha,Tucholski, Trisha,Zhu, Yanlong
, p. 8406 - 8410 (2020)
Mass spectrometry (MS)-based proteomics provides unprecedented opportunities for understanding the structure and function of proteins in complex biological systems; however, protein solubility and sample preparation before MS remain a bottleneck preventing high-throughput proteomics. Herein, we report a high-throughput bottom-up proteomic method enabled by a newly developed MS-compatible photocleavable surfactant, 4-hexylphenylazosulfonate (Azo) that facilitates robust protein extraction, rapid enzymatic digestion (30 min compared to overnight), and subsequent MS-analysis following UV degradation. Moreover, we developed an Azo-aided bottom-up method for analysis of integral membrane proteins, which are key drug targets and are generally underrepresented in global proteomic studies. Furthermore, we demonstrated the ability of Azo to serve as an “all-in-one” MS-compatible surfactant for both top-down and bottom-up proteomics, with streamlined workflows for high-throughput proteomics amenable to clinical applications.
Copper-catalyzed oxidative aromatization of 2-cyclohexen-1-ones to phenols in the presence of catalytic hydrogen bromide under molecular oxygen
Kikushima, Kotaro,Nishina, Yuta
, p. 20150 - 20156 (2013/11/06)
Catalytic oxidative aromatization has been achieved using 2-cyclohexen-1-ones to obtain phenol derivatives in the presence of a catalytic amount of copper salt and aqueous HBr under molecular oxygen. The amount of HBr was successfully reduced to a catalytic quantity, and the other additive such as a ligand and an oxidant as well as inert conditions were unnecessary. Various mono-, di-, and trisubstituted phenols with substituents at the desired positions could be synthesized under cheap and simple conditions. An oxidative aromatization/bromination sequence was also demonstrated to obtain bromophenols with excess HBr. The Royal Society of Chemistry 2013.
Development of odorless organosulfur reagents and asymmetric reaction using odorless thiols
Node, Manabu,Kajimoto, Tetsuya
, p. 572 - 583 (2008/02/08)
Odorless organosulfur reagents were developed by increasing their molecufar weights to suppress vohtility. 1-Dodecanethiol (4), dodecyl methyl sulfide (5), p-heptylphenylmethanethiol (6), p-dodecylbenzenethiol (7), p-heptylbenzenethiol (8), 2-dodecyl-l,3-propanedithiol (11), p-octyloxyphenylmethanethiol (18b,), and p-octyloxybenzenethiol (19) are typical examples of the odorless thiols and sulfides. 6-Morpholinohexyl thiol (15), methyl 6-morpholinohexyl sulfide (16) and methyl 6-morpholinohexyl sulfoxide (17,) were also developed as separable reagents from reaction products by facile acid-base extraction. In addition, p-tetramethylsilylphenylmethanethiol (18) and p-tetramethylsilylbenzenethiol (14) were synthesized as the odorless synthetic substitutes of benzyl mercaptan and benzenethiol, respectively. In a similar way, silylated diphenyl disulfide (26) and diselenide (21) were prepared as odorless disulfide and diselenide. Moreover, 10-sulfanylisobomeol (1) was found to be an excellent chiral odorless substitute of hydrogen sulfide in Michael addition.
Synthesis and Antimicrobial Activity of Hydroxyalkyl- and Hydroxyacyl-phenols and Their Benzyl Ethers
Krauss, J.,Unterreitmeier, D.
, p. 94 - 98 (2007/10/03)
New phenolic compounds with hydrophilic side chains were prepared from 4-benzyloxybenzaldehyde and alkenyl magnesium bromides, followed by Sharpless dihydroxylation and hydrogenolytic removal of the benzyl group. The resulting compounds were tested in an agar diffusion assay against gram positive bacteria, gram negative bacteria, and against the fungi Candida glabrata and Aspergillus niger.
Metal cation-exchanged montmorillonite (Mn+-mont)-catalysed aromatic alkylation with aldehydes and ketones
Tateiwa, Jun-Ichi,Hayama, Ei,Nishimura, Takahiro,Uemura, Sakae
, p. 1923 - 1928 (2007/10/03)
The alkylation of aromatic compounds with aldehydes and ketones in the presence of a variety of metal cation-exchanged montmorillonites (Mn+-mont; Mn+ = Zr4+, Al3+, Fe3+, Zn2+, H+, Na+) has been investigated. Al3+- and Zr4+-Monts are revealed to be effective as catalysts, while no reaction takes place with Na+-mont. Al3+-Mont-catalysed alkylation of phenol with several aldehydes produces mainly or almost solely the corresponding gem-bis(hydroxyphenyl)alkanes (bisphenols) in good yields, while that with several ketones affords selectively the corresponding alkylphenols in moderate to good yields. The alkylation always occurs at the carbonyl carbon without any skeletal rearrangement and the kind of products depends much on the steric hindrance of an electrophilic intermediary carbocation. The alkylation of anisole, veratrole and p-cresol proceeds well, while that of toluene, benzene, chlorobenzene and nitrobenzene scarcely occurs.
Tilt Angle Variation as a Function of Chain Length and Temperature in the Smectic C Phases of p,Alkoxyphenyl-p,Alkoxybenzoates
Heinrich, B.,Guillon, D.
, p. 21 - 44 (2007/10/02)
The variation of the tilt angle with temperature in the smectic C phase has generally been shown to be non-existent or very slow for compounds or mixtures with the nematic-smectic C transition, while in the case of systems with the smectic A-smectic C transition, a relation between the steepness of this variation, near the transition, and the width of the smectic A domain has been observed.In this work, the variation of tilt angle in the smectic C phase is described for p-alkoxyphenyl-p-alkoxybenzoate homologous series, for which the evolution of polymorphism can be controlled systematically, by varying stepwise the length of the aliphatic chains, and for which large domains can be obtained for each type of phase sequence, nematic-, smectic A- and isotropic-smectic C.After completing the discussion made previously on the incidence of chain length on polymorphism, we confirm that the variation of tilt angle with temperature is slowest for compounds with intermediate chain lengths corresponding to the largest smectic A temperature range; this variation becomes continuously steeper when the smectic A domain becomes narrow.In addition, we show that the same description can be extended to the other types of phase sequences, by using the hypothesis of a virtual smectic A-smectic C transition above the observed nematic- or isotropic-smectic C transition.In fact, short chain lengths for homologues with a nematic/smectic C transition, or long chain lengths for homologues with an isotropic/smectic C transition, lead to an increase of the tilt angle at the phase transition and to a decrease of the amplitude of its variation with temperature; in our description, this behaviour corresponds to an increase of the temperature range between the real and virtual transitions.As a consequence, the homologues with very short and very long chain lengths show a quasi temperature-independent tilt angle, while the other homologues present a tilt angle variation similar to that observed for compounds exhibiting a smectic C/smectic A transition.This feature indicates that there is no need to distinguish between different types of smectic C phase.
Aliphatic Liquid Crystals, 2. Some Nematic Derivatives of all-trans-Perhydrophenanthrene
Sucrow, Wolfgang,Minas, Hermann,Stegemeyer, Horst,Geschwinder, Peter,Murawski, Hans-Ruediger,Krueger, Carl
, p. 3332 - 3349 (2007/10/02)
A stereoselective synthesis of the all-trans-7-alkylperhydro-2-phenanthrenols 15a-f in 11 steps and 28 liquid crystalline esters 16 of 15a-f are described, additionally some further derivatives of 7-alkylperhydro-2-phenanthrenol.An X-ray structure analysis of ester 16ec is reported.
