52507-49-0Relevant academic research and scientific papers
Stereoselective synthesis of aryl 1,2-cis-furanosides and its application to the synthesis of the carbohydrate portion of antibiotic hygromycin A
Xu, Yuan,Bin, Hua-Chao,Su, Fu,Yang, Jin-Song
, p. 1548 - 1552 (2017)
An efficient methodology for the synthesis of aryl 1,2-cis-furanosidic linkages has been developed with 2-quinolinecarbonyl (Quin) group substituted furanose ethyl thioglycosides as glycosyl donors. The method permits a wide range of phenol acceptors to b
Enantiopure C1-Cyclotriveratrylene with a Reversed Spatial Arrangement of the Substituents
Long, Augustin,Colomban, Cedric,Jean, Marion,Albalat, Muriel,Vanthuyne, Nicolas,Giorgi, Michel,Di Bari, Lorenzo,Górecki, Marcin,Dutasta, Jean-Pierre,Martinez, Alexandre
supporting information, p. 160 - 165 (2019/01/04)
Cyclotriveratrylene (CTV) is a macrocyclic cyclophane presenting a bowl-shaped conformation, used as building block to construct cryptophane and hemicryptophane capsules. A method to synthesize new enantiopure CTV derivatives with an unprecedented spatial
Synthesis of a Photo-Caged DOPA Derivative by Selective Alkylation of 3,4-Dihydroxybenzaldehyde
Schneider, Tobias,Kubyshkin, Vladimir,Budisa, Nediljko
, p. 2053 - 2063 (2018/05/31)
Natural and synthetic polymers containing the catechol moiety of noncoded amino acid 3,4-dihydroxyphenylalanine (DOPA) are capable of metal-coordination and adhesion under wet conditions. Masking the catechol subunit with a photo-cleavable group would provide an opportunity to design tunable adhesion properties that are especially important for biomaterial and biomedicine applications. Herein, we report the regioselective synthesis of a photo-caged DOPA bearing an ortho-nitrobenzyl (oNB) group that is capable of undergoing cleavage upon irradiation with UV light. We developed a selective synthetic route towards a 3-O-oNB alkylated DOPA regioisomer that can be readily incorporated into proteins by using a previously developed bio-expression platform. The synthesis is based on a regioselectivity switch in 3,4-dihydrozybenzaldehyde alkylation upon application of different equivalents of deprotonating base. The enantiomerically pure 3-O-oNB-DOPA was prepared on a gram scale and proved to be generally compatible with the solid-phase peptide synthesis conditions. We also demonstrate the general applicability of the developed synthetic strategy by providing the synthesis of 3-O-methyl-DOPA.
Enzymatic allylation of catechols
Zhang, Yixin,Liu, Wujun,Sohail, Muhammad,Wang, Xueying,Liu, Yuxue,Zhao, Zongbao K.
supporting information, p. 949 - 951 (2015/08/24)
Enzymatic allylation of catechols was realized via catechol O-methyltransferase (COMT) using an allylated S-adenosyl- L-methionine (allyl-SAM) analog, with relatively good chemoand regioselectivities. This new reaction offered an alternative procedure for allylation of catechols, which can be expanded as a biocatalytic allylation method in organic synthesis.
A Biomimetic Strategy to Access the Silybins: Total Synthesis of (-)-Isosilybin A
McDonald, Benjamin R.,Nibbs, Antoinette E.,Scheidt, Karl A.
supporting information, p. 98 - 101 (2015/07/28)
(Figure Presented). We report the first asymmetric, total synthesis of (-)-isosilybin A. A late-stage catalytic biomimetic cyclization of a highly functionalized chalcone is employed to form the characteristic benzopyranone ring. A robust and flexible app
Shorter synthesis of trifunctionalized cryptophane - A derivatives
Taratula, Olena,Hill, P. Aru,Bai, Yubin,Khan, Najat S.,Dmochowski, Ivan J.
scheme or table, p. 1414 - 1417 (2011/05/13)
Efficient syntheses of trisubstituted cryptophane-A derivatives that are versatile host molecules for many applications are reported. Trihydroxy cryptophane was synthesized in six or seven steps with yields as high as 9.5%. By a different route, trihydrox
Studies on synthesis and structure-activity relationship (SAR) of derivatives of a new natural product from marine fungi as inhibitors of influenza virus neuraminidase
Li, Jing,Zhang, Dingmei,Zhu, Xun,He, Zhenjian,Liu, Shu,Li, Mengfeng,Pang, Jiyan,Lin, Yongcheng
experimental part, p. 1887 - 1901 (2011/12/04)
Based on the natural isoprenyl phenyl ether from a mangrove-derived fungus, 32 analogues were synthesized and evaluated for inhibitory activity against influenza H1N1 neuraminidase. Compound 15 (3-(allyloxy)-4-hydroxybenzaldehyde) exhibited the most potent inhibitory activity, with IC50 values of 26.96 μM for A/GuangdongSB/01/2009 (H1N1), 27.73 μM for A/Guangdong/03/2009 (H1N1), and 25.13 μM for A/Guangdong/05/2009 (H1N1), respectively, which is stronger than the benzoic acid derivatives (～mM level). These are a new kind of non-nitrogenous aromatic ether Neuraminidase (NA) inhibitors. Their structures are simple and the synthesis routes are not complex. The structure-activity relationship (SAR) analysis revealed that the aryl aldehyde and unsubstituted hydroxyl were important to NA inhibitory activities. Molecular docking studies were carried out to explain the SAR of the compounds, and provided valuable information for further structure modification.
Towards the development of a covalently tethered MALDI system - A study of allyl-modified MALDI matrixes
Martic, Sanela,Brennan, John D.,Brook, Michael A.,Ackloo, Suzanne,Nagy, Noemi
, p. 66 - 76 (2008/02/02)
An emerging application of matrix-assisted laser desorption ionization (MALDI) mass spectrometry is the analysis of low molecular weight (LMW) compounds, often via coupled, liquid chromatography - MALDI-MS methods. However, in many cases, the low molecular weight region of MALDI mass spectra is obscured by the presence of signals originating from the matrix, suggesting that the development of tethered MALDI matrixes may be required to optimize MS performance for such compounds. To gain insight into potential sites for covalent attachment of MALDI matrixes, we have systematically investigated the role played by a variety of functional group motifs in determining matrix efficiency for three common MALDI matrixes, as judged both by total signal intensity and background noise from matrix decomposition for a set of LMW compounds. A series of allyl derivatives of standard matrixes was prepared, and the efficiency of these materials in the MALDI experiment was measured. All modifications of established matrixes, e.g., 2,5-dihydroxybenzoic acid (DHB), α-cyano-4-hydroxycinnamic acid (CHCA), and caffeic acid (CA), or close analogues led to decreased absolute signal intensity and signal-to-background levels. Improved performance was generally observed with (i) the presence of a phenolic group (carboxylic acids were less effective) (ii) crystalline derivatives, and (iii) compounds that had high extinction coefficients at wavelengths near to that of the exciting laser (337 nm). The most interesting derivatives were the O-allyl ether (15) and N-allyl amide (16) of caffeic acid. These compounds did not facilitate signals from all four analytes tested. However, the observed spectra contained fewer signals from the matrix than from the parent compound CA. These compounds demonstrate that functionalization of MALDI matrixes, ultimately leading to tethered matrixes, is possible without jeopardizing signal intensity.
Investigation of selective mono-deallylation of O,O′-diallylcatechols and 3-methylene-1,5-benzodioxepanes
Hayashida, Maiko,Ishizaki, Miyuki,Hara, Hiroshi
, p. 1299 - 1303 (2008/09/20)
Selective mono-deallylation of O,O′-diallylcatechols using 10% Pd/C was investigated to give the corresponding allylphenols. A similar reaction of 3-methylene-1,5-benzodioxepanes afforded O-methacryl catecohols. When substrates bearing various substituents on the benzene ring were subjected to the reaction, regioselective cleavage of an ether bond occurred at the side of para position to an electron-withdrawing group on the aromatic ring. On the other hand, an electron-donating group did not cause any selectivity.
