55124-29-3Relevant articles and documents
Exploring the synthetic potential of a marine transaminase including discrimination at a remote stereocentre
Schwarz, Maria,Murphy, Edel J.,Foley, Aoife M.,Woods, David F.,Castilla, Ignacio Abreu,Reen, F. Jerry,Collins, Stuart G.,O'gara, Fergal,Maguire, Anita R.
, p. 188 - 198 (2021/01/18)
The marine transaminase, P-ω-TA, can be employed for the transamination from 1-aminotetralins and 1-aminoindanes with differentiation of stereochemistry at both the site of reaction and at a remote stereocentre resulting in formation of ketone products with up to 93% ee. While 4-substituents are tolerated on the tetralin core, the presence of 3- or 8-substituents is not tolerated by the transaminase. In general P-ω-TA shows capacity for remote diastereoselectivity, although both the stereoselectivity and efficiency are dependent on the specific substrate structure. Optimum efficiency and selectivity are seen with 4-haloaryl-1-aminotetralins and 3-haloaryl-1-aminoindanes, which may be associated with the marine origin of this enzyme. This journal is
Weinreb Amide as Secondary Station for the Dibenzo-24-crown-8 in a Molecular Shuttle
Gauthier, Maxime,Coutrot, Frédéric
supporting information, p. 3391 - 3395 (2019/02/19)
Here is reported the synthesis of a new molecular shuttle: it consists of a dibenzo-24-crown-8 (DB24C8) that surrounds a molecular axle containing an ammonium group and a newly considered Weinreb amide as stations. At the protonated state the DB24C8 is localized around the best ammonium station, while deprotonation-carbamoylation of the ammonium triggers the shuttling of the macrocycle around the Weinreb amide site. Further post-interlocking modification of the [2]rotaxane was attempted through the cleavage of the Weinreb amide bond using a Grignard reagent. While the non-interlocked molecular axle was cleaved after a short time in mild conditions, the Weinreb amide bond remained unaltered in the [2]rotaxane species over time, even in the presence of a larger amount of Grignard and at a higher temperature, highlighting the protection shield of the macrocycle around the encircled axle.
N-, α-, and β-substituted 3-aminopropionic acids: Design, syntheses and antiseizure activities
Tan,Wainman,Weaver
, p. 113 - 121 (2007/10/03)
A treatment for epilepsy is proposed based on analogues of 3-aminopropionic acid (β-alanine), a putative neurotransmitter in the central nervous system (CNS). A model three point pharmacophore was proposed based on modelling data obtained from the study of antagonists for both the glial γ-aminobutyric acid (GABA)-uptake site and the glycine co-agonist site of N-methyl-D-aspartate (NMDA) receptor. Three series of 3-aminopropionic acids containing, N-, α-, and β-substituents, were designed and synthesized to probe the position and the size of a lipophilic binding pocket within the proposed pharmacophore. These analogues were tested in vivo for both their antiseizure activities and their neurologic toxicities. Among the fourteen novel 3-aminopropionic acids synthesized, eight were found to have promising antiseizure activity. This study shows that substitution on the N-terminus confers the greatest antiseizure activity, particularly against pilocarpine-induced seizures.
