- Activatable fluorescent probes for hydrolase enzymes based on coumarin-hemicyanine hybrid fluorophores with large Stokes shifts
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We show that the equilibrium of intramolecular spirocyclization of coumarin-hemicyanine hybrid fluorophores can be finely tuned by means of chemical modifications. We used this scaffold to develop activatable fluorescent probes with large Stokes shifts for γ-glutamyltranspeptidase and esterase.
- Fujioka, Hiroyoshi,Johnsson, Kai,Kamiya, Mako,Kojima, Ryosuke,Uno, Shin-Nosuke,Urano, Yasuteru
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supporting information
p. 5617 - 5620
(2020/06/18)
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- Compounds
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The present invention relates to a compound which is N-(4-{4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinyl}butyl)ethanesulfonamide and salts thereof, processes for its preparation, to compositions containing it and to its use in the treatment of various diseases, such as allergic rhinitis.
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Page/Page column 23
(2009/10/31)
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- Molecular addition compounds. 18. Borane adducts with hydroxydialkyl sulfide borates for hydroboration. New, essentially odorless, water-soluble sulfide borane acceptors for hydroboration
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Hydroxydialkyl sulfides of general formula RS(CH2CH2)nH (R = Et, t-Bu, i-Am; n = 1-3) and thiodiethanol monomethyl ether (9) have been synthesized and used as borane carriers. The compounds 3 and 6 (R = Et, n = 2, 3), 7 (R = t-Bu, n = 3), and 9 are completely miscible with water and exhibit only very mild odor. The sulfides were transformed into the corresponding borates by treatment either with boric acid or with diborane. The borates complex 3 mol of borane per 1 mol of borate to give highly reactive, stable, liquid adducts, hydroborating 1-octene in 15 min at room temperature. The adducts derived from water soluble sulfides 3 and 9, selected for the hydroboration of more hindered olefins, reacted readily with (-)-β-pinene, 1-methyleyclohexene, and 2,3-dimethyl-2-butene. The carrier borates liberated from the adducts during hydroboration are readily hydrolyzed to give 3 and 9, which can be washed off with water from trialkylboranes or oxidation products. Consequently, hydroxydialkyl sulfides 3 and 9 are the first completely water-soluble sulfide borane carriers that can be washed off in the workup of hydroboration products. The adducts derived from 3 and 9 are new, highly promising reagents suitable for large scale hydroborations and reductions.
- Brown,Zaidlewicz,Dalvi,Biswas
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p. 4795 - 4798
(2007/10/03)
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- Lipase catalyzed resolution of α-hydroxymethyl sulfones. Determination of absolute configuration by semiempirical calculation of CD spectra and verification by X-ray structure analysis
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The Candida antarctica lipase catalyzed esterification of the hydroxymethyl sulfones rac-1a and rac-1b led to the isolation of ent-1a (92% ee) and 1b (≤99% eel, respectively. The acyloxymethyl sulfone ent-7a (≤99% ee) was obtained by the Candida antarctica lipase catalyzed hydrolysis of rac-7a. Not only Candida antarctica lipase but also Pseudomonas cepacia lipase showed the opposite enantiomer differentiation in the esterification of the methyl substituted alcohol rac-1a and the benzyl substituted alcohol rac-1b. The absolute configuration of ent-1a and 1b was determined by measurement of their circular dichroism and the calculation of the CD spectra of 1a and 1b by semiempirical methods. The configurational assignment was verified by X-ray structure analysis of 1b and ent-7a.
- Gais, Hans-Joachim,Von Der Weiden, Ingo,Fleischhauer, Joerg,Esser, Josef,Raabe, Gerhard
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p. 3111 - 3123
(2007/10/03)
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- Preparation of enantiomerically pure α-hydroxymethyl S-tert-butyl sulfones by Candida antarctica lipase catalyzed resolution
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Candida antarctica lipase (CAL; Novozym 435) catalyzed acylation of racemic methyl and benzyl substituted hydroxy sulfones rac-3a and rac-3d, respectively, with vinyl acetate either neat or in ether solvents proceeded with E-values of 18 and 49. For the CAL catalyzed hydrolysis of methyl substituted acetoxy sulfone rac-4a in an emulsion of phosphate buffer and methyl tert-butyl ether at pH 7.0 an E-value of 22 was found. Acetate (+)-ent-4a as well as alcohols (-)-3a and (-)-(S)-3d were obtained with ee-values of 99% on a gram scale.
- Gais, Hans-Joachim,Von Der Weiden, Ingo
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p. 1253 - 1256
(2007/10/03)
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- SYNTHESIS OF POLYSULFIDES, SULFOXIDES AND SULFONES CONTAINING REACTIVE GROUPS
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Preparation of polysulfides, sulfoxides and sulfones (containing reactive groups: OH, Cl, COOR, CN, SO3Na) are presented; 13C chemical shifts of these compounds have been recorded.Keywords: Sulfide; sulfoxide; sulfone; chlorosulfide; 1H NMR; 13C NMR.
- Aberkane, O.,Mieloszynski, J. L.,Robert, D.,Born, M.,Paquer, D.
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p. 245 - 256
(2007/10/02)
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