2279-15-4Relevant articles and documents
Beyond the Diketopiperazine Family with Alternatively Bridged Brevianamide F Analogues
Wauters,Goossens,Delbeke,Muylaert,Roman,Van Hecke,Van Speybroeck,Stevens
, p. 8046 - 8054 (2015/09/02)
A method for the preparation of 3,5-bridged piperazin-2-ones from a tryptophan-proline-based diketopiperazine is described using diphosgene to induce the ring closure. Density functional theory calculations were conducted to study the mechanism of this C-C bond formation. Several derivatives of the thus obtained α-chloroamine were synthesized by substitution of the chlorine atom using a range of O-, N-, S-, and C-nucleophiles. This novel class of brevianamide F analogues possess interesting breast cancer resistance protein inhibitory activity.
A concise preparation of the non-proteinogenic amino acid l-kynurenine
Kleijn, Laurens H.J.,Müskens, Frederike M.,Oppedijk, Sabine F.,De Bruin, Gerjan,Martin, Nathaniel I.
supporting information, p. 6430 - 6432 (2013/01/15)
A concise and practical preparation of the non-proteinogenic amino acid l-kynurenine is reported. The synthetic approach is scalable and provides ready access to this valuable amino acid in either l- or d-stereochemistry starting from l- or d-tryptophan, respectively. In the optimized procedure, two discreet oxidation steps are applied sequentially to convert the tryptophan indole ring into the keto-aniline moiety contained within the kynurenine side chain.
Cyclodextrin-mediated deacylation of amino acid esters with marked stereoselectivity.
Goto, Koichi,Nakashima, Kentaro,Tanoue, Osamu,Nukushina, Satoshi,Toudo, Isao,Imamura, Chikara,Ihara, Yasuji,Matsumoto, Yoko,Ueoka, Ryuichi
, p. 1283 - 1285 (2007/10/03)
With respect to the hydrolysis (deacylation) of Z-D(L)-amino acid esters (N-(benzyloxycarbonyl)-D(L)-amino acid p-nitrophenyl esters) mediated by alpha-, beta- and gamma-cyclodextrins (CyDs), a remarkably high enantioselectivity (L/D=9.0) was observed for the deacylation of Ala substrate with gamma-CyD. The kinetic results on the basis of the Michaelis-Menten principle indicate that the enantioselectivity should be mainly originated in the deacylation process of substrates following the formation of gamma-CyD-substrate (1 : 1) complexes. The computer modeling (molecular mechanics) studies on the inclusion complexes are also described.