Association Behavior of 1-Pyrenyl Pendants Introduced into the Papain Active Site was written by Sakurai, Tadamitsu;Miyata, Kazue;Watanabe, Kenichiro;Kubo, Kanji;Inoue, Hiroyasu. And the article was included in Bulletin of the Chemical Society of Japan in 1999.Product Details of 80480-15-5 The following contents are mentioned in the article:
1-(Bromoacetyl)pyrene (BAP) was found to selectively alkylate the cysteine-25 residue (Cys-25) of papain, inactivating the enzyme. A comparison of the spectroscopic behavior of BAP-modified papain with that of the reference compound, 1-{[2-(acetylamino)ethylthio]acetyl}pyrene (TAP), showed that the pyrenecarbonylmethyl pendant (covalently bound to Cys-25 in a 1:1 stoichiometric ratio) gives a new absorption around 390 nm and a long-wavelength fluorescence at 465 nm, which are both characteristic of an associated dimer. Effects of solvent and concentration on the absorption and emission spectra of TAP as well as the derivatized enzyme substantiate the dimer formation in the ground state. The finding that the pendant-carbonyl-13C carbon signal undergoes a large upfield shift in the papain active site, as compared to the corresponding signal of 13C-labeled TAP, confirms that the pyrenecarbonyl moiety adopts an enolate-type resonance structure (making the pyrene ring electron-deficient) on formation of a strong hydrogen bond to the neighboring amino acid residue(s). It is proposed that the significant contribution of the enolate-type resonance structure is a driving force for promoting the dimerization of the pyrenecarbonylmethyl reporter group attached to Cys-25 mainly through dipole-dipole and hydrophobic interactions. On the other hand, the introduction of the imino spacer between the 1-pyrenyl carbon and the acetyl carbonyl carbon in BAP-derived pendant greatly weakened a tendency to produce a pendant dimer in the ground state, providing a piece of evidence in support of this proposal. This study involved multiple reactions and reactants, such as 2-Bromo-1-(pyren-1-yl)ethanone (cas: 80480-15-5Product Details of 80480-15-5).
2-Bromo-1-(pyren-1-yl)ethanone (cas: 80480-15-5) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Product Details of 80480-15-5
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary