132161-97-8Relevant academic research and scientific papers
A Modular Synthesis of Conformationally Preorganised Extended β-Strand Peptidomimetics
Yamashita, Tohru,Knipe, Peter C.,Busschaert, Nathalie,Thompson, Sam,Hamilton, Andrew D.
, p. 14699 - 14702 (2015)
A promising strategy for mediating protein-protein interactions is the use of non-peptidic mimics of secondary structural protein elements, such as the α-helix. Recent work has expanded the scope of this approach by providing proof-of-principle scaffolds that are conformationally biased to mimic the projection of side-chains from one face of another common secondary structural element - the β-strand. Herein, we present a synthetic route that has key advantages over previous work: monomers bearing an amino acid side-chain were pre-formed before rapid assembly to peptidomimetics through a modular, iterative strategy. The resultant oligomers of alternating pyridyl and six-membered cyclic ureas accurately reproduce a recognition domain of several amino acid residues of a β-strand, demonstrated herein by mimicry of the i, i+2, i+4 and i+6 residues.
Stereoselective synthesis of 2,4,5-trisubstituted piperidines via radical cyclization
Ragoussi, Maria-Eleni,Walker, Stephen M.,Piccanello, Andrea,Kariuki, Benson M.,Horton, Peter N.,Spencer, Neil,Snaith, John S.
, p. 7347 - 7357 (2011/02/16)
A novel approach to 2,4,5-trisubstituted piperidines is reported, involving the 6-exo cyclization of stabilized radicals onto α,β-unsaturated esters. Only two of the four possible diastereoisomers are observed, with diastereomeric ratios ranging from 3:2
Substituted 1,4-benzoxazepines, 1,5-benzoxazocines, and N- and S-variants
Rujirawanich, Janjira,Gallagher, Timothy
supporting information; experimental part, p. 5494 - 5496 (2010/02/28)
"Chemical Equation Presented" Nucleophilic cleavage of enantiomerically pure 1,2-cyclic sulfamidates with phenol, aniline, and thiophenol nucleophiles, followed by a Mitsunobu reaction, including use of a o-quinomethide variant of this process, provides a
Synthesis and biological evaluation of reversible inhibitors of IdeS, a bacterial cysteine protease and virulence determinant
Berggren, Kristina,Johansson, Bjoern,Fex, Tomas,Kihlberg, Jan,Bjoerck, Lars,Luthman, Kristina
experimental part, p. 3463 - 3470 (2009/09/25)
Analogues of the irreversible protease inhibitors TPCK and TLCK have been synthesized and tested as inhibitors of the bacterial cysteine protease IdeS excreted by Streptococcus pyogenes. Eight compounds were identified as inhibitors of IdeS in an in vitro
Stereoselective synthesis of 2,4,5-trisubstituted piperidines by carbonyl ene and Prins cyclisations
Cariou, Claire A.M.,Kariuki, Benson M.,Snaith, John S.
supporting information; experimental part, p. 3337 - 3348 (2009/02/05)
An approach to 2,4,5-trisubstituted piperidines is reported, in which the key step is the Prins or carbonyl ene cyclisation of aldehydes of the type 1. Prins cyclisation catalysed by concentrated hydrochloric acid in CH 2Cl2 at -78 °C afforded good yields of two of the four possible diastereomeric piperidines, with the 4,5-cis product 7 predominating in a diastereomeric ratio of up to 94: 6. The diastereoselectivity of the cyclisation decreased as the 2-substituent increased in size, becoming unselective for very bulky 2-substituents. In contrast, cyclisation catalysed by MeAlCl2 in CH2Cl2 or CHCl3 at temperatures of between 20-60 °C, favoured the 4,5-trans diastereomer 8, in a diastereomeric ratio of up to 99: 1. The low-temperature cyclisations catalysed by HCl proceed under kinetic control via a mechanism involving the development of significant carbocationic character, in which the 4,5-cis cation is more stable than the 4,5-trans cation as a result of overlap with the neighbouring oxygen. The cyclisations catalysed by MeAlCl2 proceed under thermodynamic control, affording the product in which both the 4- and 5-substituents are equatorial.
A convenient synthetic route to enantiopure N-tosylazetidines from α-amino acids
Ghorai, Manas K.,Das, Kalpataru,Kumar, Amit
, p. 2471 - 2475 (2007/10/03)
A general and convenient synthetic route to various chiral 2-substituted- and 2,4-disubstituted-N-tosylazetidines (ee >99%) is described in good overall yields starting from chiral α-amino acids using very simple chemistry.
Stereoselective synthesis of 2,4,5-trisubstituted piperidines by carbonyl ene and Prins cyclisations
Cariou, Claire A. M.,Snaith, John S.
, p. 51 - 53 (2007/10/03)
Intramolecular carbonyl ene reactions present a method for ring closure, leading to the formation of two contiguous stereocentres with an often high degree of stereocontrol. The extension of this approach to the synthesis of 2,4,5-trisubstituted piperidin
Synthesis of enantiopure β- and γ-amino alcohols from homochiral α- and β-aminoacylsilanes as stable synthetic equivalents of α- and β-amino aldehydes
Bonini, Bianca Flavia,Comes-Franchini, Mauro,Fochi, Mariafrancesca,Gawronski, Jacek,Mazzanti, Germana,Ricci, Alfredo,Varchi, Greta
, p. 437 - 445 (2007/10/03)
A practical route is described for the synthesis of enantiopure β- and γ-amino alcohols with two stereocenters, starting from homochiral α- (1 and 5) and β- (13 and 16) -aminoacylsilanes, and involving stereoselective addition of allylmetal compounds and subsequent stereospecific protiodesilylation of the adducts. The degree of diastereoselectivity achieved in the nucleophilic addition step depends on both the nitrogen- protecting group and the reagents used. Diastereomeric excess (de) values equal to or higher than 98% were obtained in the TiCl4-promoted allylation of the N-Pht aminoacylsilanes 1 and 13 and of the N-Ts-aminoacylsilane 5 with allyltrimethylsilane. Lower de values were obtained in the Sc(OTf)3- catalyzed anylation of 5 with tetraallyltin and in the additions of both allyltrimethylsilane and tetraallyltin to the N-Ts-β-aminoacylsilane 16. Protiodesilylation of the adducts, leading to the β- and γ-amino alcohols, was accomplished with TBAF, except in the case of the adducts obtained from 5. For these, a preliminary removal of the tosyl group was necessary, which was accomplished with simultaneous desilylation by treatment with Na in liquid ammonia.
Yb(CN)3-catalyzed reaction of aziridines with cyanotrimethylsilane. A facile synthesis of optically pure β-amino nitriles
Matsubara, Seijiro,Kodama, Tomohiro,Utimoto, Kiitiro
, p. 6379 - 6380 (2007/10/02)
Reaction of a N-tosylaziridine with cyanotrimethylsilane under lanthanoid tricyanide catalysis gives a N-tosyl β-amino nitrile by selective attack of cyanide at less substituted carbon of the ring; optically pure 2-substituted aziridine affords the corres
