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Synthesis of Novel Planar-Chiral Charge-Compensated nido-Carborane-Based Amino Acid

Authors :
Dmitry A. Gruzdev
Angelina A. Telegina
Marina A. Ezhikova
Mikhail I. Kodess
Galina L. Levit
Victor P. Krasnov
Source :
Molecules, Vol 29, Iss 18, p 4487 (2024)
Publication Year :
2024
Publisher :
MDPI AG, 2024.

Abstract

Amino acids with unusual types of chirality and their derivatives have recently attracted attention as precursors in the synthesis of chiral catalysts and peptide analogues with unique properties. In this study, we have synthesized a new nido-carborane-based planar-chiral amino acid, in the molecule of which the amino group is directly bonded to the B(3) atom, and the carboxyl group is attached to the B(9) atom through the CH2S+(Me) fragment. 3-Amino-9-dimethylsulfonio-nido-carborane, prepared in three steps from 3-amino-closo-carborane in a high yield, was a key intermediate in the synthesis of the target planar-chiral amino acid. The carboxymethyl group at the sulfur atom was introduced by the demethylation reaction of the dimethylsulfonio derivative, followed by S-alkylation. The structure of new 3,9-disubstituted nido-carboranes was studied for the first time using NMR spectroscopy. The resonances of all boron atoms in the 11B NMR spectrum of 3-amino-9-dimethylsulfonio-nido-carborane were assigned based on the 2D NMR correlation experiments. The nido-carborane-based planar-chiral amino acid and related compounds are of interest as a basis for peptide-like compounds and chiral ligands.

Details

Language :
English
ISSN :
29184487 and 14203049
Volume :
29
Issue :
18
Database :
Directory of Open Access Journals
Journal :
Molecules
Publication Type :
Academic Journal
Accession number :
edsdoj.f1325d6bf3e549e59e173d8b10eba918
Document Type :
article
Full Text :
https://doi.org/10.3390/molecules29184487