Synthesis of novel zwitterionic nido-carborane-containing derivatives of cysteine and methionine

Telegina, A. A.; Gruzdev, D. A.; Ezhikova, M. A.; Kodess, M. I.; Ol’shevskaya, V. A.; Levit, G. L.; Krasnov, V. P.

doi:10.1007/s11172-024-4289-4

Russ Chem Bull

2024

DOI: 10.1007/s11172-024-4289-4

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Synthesis of novel zwitterionic nido-carborane-containing derivatives of cysteine and methionine

A. A. Telegina,

D. A. Gruzdev,

M. A. Ezhikova

et al.

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2024

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Cited by 2 publications

References 52 publications

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Theoretical study of the reaction of 7,8-dicarba-nido-undecaborane with S-nucleophiles in the presence of mercury(ii) chloride

Korolyova,

Telegina,

Levit

et al. 2024

Russ Chem Bull

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Theoretical study of the reaction of 7,8-dicarba-nido-undecaborane with S-nucleophiles in the presence of mercury(ii) chloride

Korolyova,

Telegina,

Levit

et al. 2024

Russ Chem Bull

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

Gruzdev,

Telegina,

Ezhikova

et al. 2024

Molecules

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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.

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Synthesis of novel zwitterionic nido-carborane-containing derivatives of cysteine and methionine

Cited by 2 publications

References 52 publications

Theoretical study of the reaction of 7,8-dicarba-nido-undecaborane with S-nucleophiles in the presence of mercury(ii) chloride

Theoretical study of the reaction of 7,8-dicarba-nido-undecaborane with S-nucleophiles in the presence of mercury(ii) chloride

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

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