63613-10-5Relevant articles and documents
One-pot efficient synthesis of N α-urethane-protected β- And γ-amino acids
Cal, Marta,Jaremko, Mariusz,Jaremko, Lukasz,Stefanowicz, Piotr
, p. 1085 - 1091 (2013/07/05)
1-[(4-Methylphenyl)oxy]pyrrolidine-2,5-dione and 1-[(4-methylphenyl)oxy] piperidine-2,6-dione react in a Lossen-type reaction with primary alcohols in the presence of triethylamine to furnish corresponding N α- urethane-protected β-alanine and γ-aminopropionic acid (GABA), respectively, with excellent yields and purities, in an essentially "one-pot" procedure.
Studies on the Lossen-type rearrangement of N-(3-phenylpropionyloxy) phthalimide and N-tosyloxy derivatives with several nucleophiles
Chanmiya Sheikh,Takagi, Shunsuke,Ogasawara, Asako,Ohira, Masayuki,Miyatake, Ryuta,Abe, Hitoshi,Yoshimura, Toshiaki,Morita, Hiroyuki
supporting information; experimental part, p. 2132 - 2140 (2010/04/26)
The reaction of N-(3-phenylpropionyloxy)phthalimide (1a) and N-tosyloxy (5a,b) derivatives with nucleophiles was examined and found to give the products via Lossen-type rearrangement. In order to obtain the scope of this reaction mechanism, further studies the reaction of several N-sulfonyloxyimide derivatives with various nucleophiles under similar conditions were carried out and found to afford the corresponding same types of products in high yields.
Lossen-type rearrangement products in the reaction of N-(phthalimidoyloxy)-3-phenylpropionate and -tosylate with benzyl alcohol
Takagi, Shunsuke,Sheikh, Chanmiya,Ogasawara, Asako,Ohira, Masayuki,Abe, Hitoshi,Morita, Hiroyuki
experimental part, p. 1433 - 1438 (2009/12/24)
This paper reports the reaction of N-(phthalimidoyloxy)-3-phenylpropionate (2a) and -tosylate (6) with benzyl alcohol as a nucleophile to afford the products via Lossen-type rearrangement. To study the scope of this reaction mechanism, we also studied the
Expanding the utility of proteases in synthesis: Broadening the substrate acceptance in non-coded amide bond formation using chemically modified mutants of subtilisin
Khumtaveeporn, Kanjai,Ullmann, Astrid,Matsumoto, Kazutsugu,Davis, Benjamin G.,Jones
, p. 249 - 261 (2007/10/03)
The strategy of combined site directed mutagenesis and chemical modification creates chemically modified mutants (CMMs) with greatly broadened substrate specificities. We have previously reported that the CMMs of subtilisin Bacillus lentus (SBL) are efficient catalysts for the coupling of both L- and D-amino acids. We now report that these powerful catalysts also allow amide bond formation between a variety of non-coded carboxylic acids, including β-alanine and β-amino homologues of phenylalanine, with both L- and D-amino acid nucleophiles. As a guide to enzyme efficiency, a hydrolysis assay indicating pH change has been employed. CMMs selected by this screen furnished higher yields of coupling products compared to the wild-type enzyme (WT). Furthermore, both WT and CMM enzymes allow highly stereoselective aminolysis of a meso diester with an amino acid amine. These results highlight the utility of CMMs in the efficient formation of non-coded amides as potential peptide isosteres.