- Synthesis and Characterization of Optically Pure Gamma-PNA Backbones by SIBX-Mediated Reductive Amination
-
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.
- Periyalagan, Alagarsamy,Kim, Yong-Tae,Hong, In Seok
-
p. 1304 - 1309
(2021/08/09)
-
- Synthetic Studies on the Preparation of Alanyl Epoxysulfones as Cathepsin Cysteine Protease Electrophilic Traps
-
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.
- Latorre, Antonio,Rodríguez, Santiago,González, Florenci V.,Florea, Bogdan I.,Overkleeft, Herman S.
-
p. 7752 - 7756
(2015/08/18)
-
- A direct and efficient stereoconservative procedure for the selective oxidation of N-protected β-amino alcohols
-
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
- Ocejo, Marta,Vicario, Jose L.,Badía, Dolores,Carrillo, Luisa,Reyes, Efraim
-
p. 2110 - 2112
(2007/10/03)
-
- An easy and fast conversion of N2-[(tert-butoxy)carbonyl]-L-amino acids to corresponding amino-aldehydes
-
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.
- Zlatoidsky
-
p. 575 - 578
(2007/10/02)
-