71601-10-0Relevant academic research and scientific papers
Identification of an Esterase Isolated Using Metagenomic Technology which Displays an Unusual Substrate Scope and its Characterisation as an Enantioselective Biocatalyst
Gavin, Declan P.,Murphy, Edel J.,Foley, Aoife M.,Castilla, Ignacio Abreu,Reen, F. Jerry,Woods, David F.,Collins, Stuart G.,O'Gara, Fergal,Maguire, Anita R.
, p. 2466 - 2474 (2019/03/11)
Evaluation of an esterase annotated as 26D isolated from a marine metagenomic library is described. Esterase 26D was found to have a unique substrate scope, including synthetic transformations which could not be readily effected in a synthetically useful manner using commercially available enzymes. Esterase 26D was more selective towards substrates which had larger, more sterically demanding substituents (i. e. iso-propyl or tert-butyl groups) on the β-carbon, which is in contrast to previously tested commercially available enzymes which displayed a preference for substrates with sterically less demanding substituents (e.g. methyl group) at the β-carbon. (Figure presented.).
Highly enantioselective aminoacylase-catalyzed transesterification of secondary alcohols
Bakker,Spruijt,Van Rantwijk,Sheldon
, p. 1801 - 1808 (2007/10/03)
The aminoacylase (N-acyl-L-amino acid amidohydrolase; E.C. 3.5.1.14) from Aspergillus melleus, a readily available inexpensive enzyme, catalyzes the transesterification of a wide range of chiral secondary arylalkanols with essentially absolute stereoselectivity (E> 500). Moreover, the productivities obtained with 1-phenylethanol, 1-phenylpropanol, 1-(1-naphthyl)ethanol and 1- (2-naphthyl)ethanol were substantially higher than those in the corresponding lipase-catalyzed transesterifications. (C) 2000 Elsevier Science Ltd.
Reduction of Polycyclic Arenes with BH-Boranes, I. - Reactions of Naphthalene, Anthracene, and Phenanthrene with Tetraalkyldiboranes(6)
Koester, Roland,Schuessler, Wilhelm,Yalpani, Mohamed
, p. 677 - 686 (2007/10/02)
Polycyclic arenes, e.g. naphthalene (N3), acenaphthene, anthracene (A3), naphthacene, benzoanthracene, and 3,4-benzophenanthrene react without gas evolution irrversibly with organodiboranes(6) /= 130 deg C to form borylated hydroarenes and their functional derivatives.The uptake of BH borane (TPDB) is followed by analytical methods.The reactions carried out on preparative scale with N3 and either TPDB or TEDB (2-10 h, T>/= 140 deg C) result in a mixture of borylated C10 compounds, from which after oxidation and O-acetylation 1- and 2-acetoxytetralins (N4, N5), together with small amounts of tetralin (N1), can be isolated.A3 reacts forming tetrahydroanthracene (A1), 1-, and 2-acetoxytetrahydroanthracene (A4, A6) as well as single stereoisomers of 1,4- and 1,3-diacetoxytetrahydroanthracene (A10, A13), which were separated and characterized.On extended heating (64 h) of A3 with TPDB at T >/= 140 deg C, the main products are one regioisomer of acetoxyhexahydroanthracene (A5) and 6 isomers of diacetoxyoctahydroanthracene (A7-A9, A11, A12, A14).For the formation of N4, N5, A4, A6-A9, A11, A12, and A14 (deuteration experiments), a hydroboration of the arene and subsequent hydrodeboration are suggested.Organo polyboranes and/or carboranes of unknown structures are formed as sideproducts.Phenanthrene (PH), which appears to be unreactive at 130 deg C, was shown to undergo a slow deuterioboration/dehydroboration on treatment with TEDB at 150 deg C resulting in the deuterated compounds PH and PH. - Keywords: Acetoxyhydroarenes/ Anthracene/ Borylhydroarenes/ Naphthalene/ Hydroboration
