The first systematic study on the asymmetric synthesis of H-phosphinic acids bearing natural protein amino acid residues was reported on the basis of the asymmetric addition of ethyl diethoxymethylphosphinate to N-tert-butanesulfinyl imines. Good yields and moderate to high enantioselectivities were obtained. Reliable methods were developed for the elucidation of the stereochemistry of these phosphinic acids and derivatives thereof. The transformation of the side chains of these analogues was studied. Methods for the conversion of the α-aminophosphinates to oligopetides were reported.
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http://dx.doi.org/10.1021/jo400798f | DOI Listing |
J Biol Chem
October 2024
Department of Medico-Surgical Sciences and Biotechnologies, Sapienza University of Rome, Latina, Italy. Electronic address:
Desmethylphosphinothricin (L-Glu-γ-P) is the H-phosphinic analog of glutamate with carbon-phosphorus-hydrogen (C-P-H) bonds. In L-Glu-γ-P the phosphinic group acts as a bioisostere of the glutamate γ-carboxyl group allowing the molecule to be a substrate of Escherichia coli glutamate decarboxylase, a pyridoxal 5'-phosphate-dependent α-decarboxylase. In addition, the L-Glu-γ-P decarboxylation product, GABA-P, is further metabolized by bacterial GABA-transaminase, another pyridoxal 5'-phosphate-dependent enzyme, and succinic semialdehyde dehydrogenase, a NADP-dependent enzyme.
View Article and Find Full Text PDFFront Chem
August 2024
Faculty of Fundamental Medicine, M. V. Lomonosov Moscow State University, Moscow, Russia.
-Adenosyl-l-methionine (SAM)-mediated methylation of biomolecules controls their function and regulates numerous vital intracellular processes. Analogs of SAM with a reporter group in place of the -methyl group are widely used to study these processes. However, many of these analogs are chemically unstable that largely limits their practical application.
View Article and Find Full Text PDFInt J Mol Sci
December 2022
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, Arbuzov Str. 8, 420088 Kazan, Russia.
A coordination polymer has been synthesized using ferrocene-based ligand-bearing phosphinic groups of 1,1'-ferrocene-diyl-bis(-phosphinic acid)), and samarium (III). The coordination polymer's structure was studied by both single-crystal and powder XRD, TG, IR, and Raman analyses. For the first time, the Mössbauer effect studies were performed on ferrocenyl phosphinate and the polymer based on it.
View Article and Find Full Text PDFOrg Biomol Chem
December 2021
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia.
Long-chain -alkyl--phosphinic acids (Alk = C-C) are chemoselectively synthesized in yields up to 90% the direct one-pot alkylation/oxidation of red phosphorus (P) in the multi-phase alkyl bromide/KOH/HO/toluene system with alkyl-PEG recyclable micellar catalysts, which demonstrate good recyclability.
View Article and Find Full Text PDFRSC Adv
June 2020
Department of Inorganic Chemistry, Faculty of Science, Universita Karlova (Charles University) Hlavova 8/2030, 12843 Prague 2 Czech Republic +420-22195-1253 +420-22195-1263.
Aminoalkyl--phosphinic acids, also called aminoalkylphosphonous acids, are investigated as biologically active analogues of carboxylic amino acids and/or as valuable intermediates for synthesis of other aminoalkylphosphorus acids. Their synthesis has been mostly accomplished by phospha-Mannich reaction of a P-H precursor, an aldehyde and an amine. The reaction is rarely clean and high-yielding.
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