79069-50-4Relevant articles and documents
Synthesis and Characterization of Optically Pure Gamma-PNA Backbones by SIBX-Mediated Reductive Amination
Periyalagan, Alagarsamy,Kim, Yong-Tae,Hong, In Seok
, p. 1304 - 1309 (2021/08/09)
Chiral peptide nucleic acid (PNA) is a derivative of regular PNA by introducing a chiral center to its backbone, and is known to bind more strongly to DNA or RNA than regular PNA. In particular, in the case of a γ-backbone, the L isomer stabilizes the PNA/DNA duplex, and the D-isomer has the opposite effect. Therefore, the synthesis of an optically pure γ-backbone is very important. Here, we report a novel synthetic strategy for the suppression of epimerization during the synthesis of the γ-PNA backbone. A stabilized form of 2-iodoxybenzoic acid (SIBX) was used as an oxidative reagent in the key intermediate of the N-Boc-amino acetaldehyde synthesis. This paper reports (1) the synthesis and comparison of three different γ-PNA backbones (lysine, alanine, and glutamate) by three different synthetic routes (SIBX, lithium aluminum hydride, and Red-Al) and (2) the determination of chiral purity from their derivative compounds. The enantiomeric excess purity of SIBX-mediated γ-PNA backbones was determined to be more than 99.4%, as ascertained by the high-performance liquid chromatography (HPLC) chromatogram on a standard RP-C18 column. It is comparatively higher than that of the other methods examined in this work.
Synthetic Studies on the Preparation of Alanyl Epoxysulfones as Cathepsin Cysteine Protease Electrophilic Traps
Latorre, Antonio,Rodríguez, Santiago,González, Florenci V.,Florea, Bogdan I.,Overkleeft, Herman S.
, p. 7752 - 7756 (2015/08/18)
A Darzens reaction between tert-butoxycarbonyl alaninal and chloromethyl phenyl sulfone afforded chlorohydrins, which were converted into epoxysulfones by reaction with sodium tert-butoxide. Epoxysulfone 10 and chloroketone 14 derived from chlorohydrins by oxidation proved to be inhibitors of cathepsins H, S, and C as determined by competitive activity-based protein profiling.
A direct and efficient stereoconservative procedure for the selective oxidation of N-protected β-amino alcohols
Ocejo, Marta,Vicario, Jose L.,Badía, Dolores,Carrillo, Luisa,Reyes, Efraim
, p. 2110 - 2112 (2007/10/03)
An efficient, very simple and eco-friendly procedure has been developed for the synthesis of highly enantioenriched α-amino aldehydes by IBX-mediated oxidation of the corresponding β-amino alcohols. The procedure has been applied to a wide range of substr
An easy and fast conversion of N2-[(tert-butoxy)carbonyl]-L-amino acids to corresponding amino-aldehydes
Zlatoidsky
, p. 575 - 578 (2007/10/02)
A new method for the preparation of N2-[(tert-butoxy)carbonyl]-L-amino-aldehydes from N2-[(tert-butoxy)carbonyl]-L-amino acids based on reduction of mixed anhydrides with LiAl(t-BuO)3H is described.
