Synthesis of 2-Substituted (2R,4R)-3-(3-Mercapto-Propionyl)Thiazolidine-4-Carboxylic Acids

Еrshov, A. Yu.; Nasledov, D. G.; Lagoda, I. V.; Шаманин, В. В.

doi:10.1007/s10593-014-1560-x

Cited by 12 publications

(6 citation statements)

References 16 publications

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“…We synthesized IT4C from L-cysteine and 3-methylbutanal according to Ershov et al. ( 41 ), and verified the structure by proton NMR analysis ( SI Appendix , Fig. S5 ).…”

Section: Resultsmentioning

confidence: 99%

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A flavin-dependent monooxygenase produces nitrogenous tomato aroma volatiles using cysteine as a nitrogen source

Liscombe

Kamiyoshihara

Ghironzi

et al. 2022

Proc. Natl. Acad. Sci. U.S.A.

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Tomato (Solanum lycopersicum) produces a wide range of volatile chemicals during fruit ripening, generating a distinct aroma and contributing to the overall flavor. Among these volatiles are several aromatic and aliphatic nitrogen-containing compounds for which the biosynthetic pathways are not known. While nitrogenous volatiles are abundant in tomato fruit, their content in fruits of the closely related species of the tomato clade is highly variable. For example, the green-fruited species Solanum pennellii are nearly devoid, while the red-fruited species S. lycopersicum and Solanum pimpinellifolium accumulate high amounts. Using an introgression population derived from S. pennellii, we identified a locus essential for the production of all the detectable nitrogenous volatiles in tomato fruit. Silencing of the underlying gene (SlTNH1;Solyc12g013690) in transgenic plants abolished production of aliphatic and aromatic nitrogenous volatiles in ripe fruit, and metabolomic analysis of these fruit revealed the accumulation of 2-isobutyl-tetrahydrothiazolidine-4-carboxylic acid, a known conjugate of cysteine and 3-methylbutanal. Biosynthetic incorporation of stable isotope-labeled precursors into 2-isobutylthiazole and 2-phenylacetonitrile confirmed that cysteine provides the nitrogen atom for all nitrogenous volatiles in tomato fruit. Nicotiana benthamiana plants expressing SlTNH1 readily transformed synthetic 2-substituted tetrahydrothiazolidine-4-carboxylic acid substrates into a mixture of the corresponding 2-substituted oxime, nitro, and nitrile volatiles. Distinct from other known flavin-dependent monooxygenase enzymes in plants, this tetrahydrothiazolidine-4-carboxylic acid N-hydroxylase catalyzes sequential hydroxylations. Elucidation of this pathway is a major step forward in understanding and ultimately improving tomato flavor quality.

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“…We synthesized IT4C from L-cysteine and 3-methylbutanal according to Ershov et al. ( 41 ), and verified the structure by proton NMR analysis ( SI Appendix , Fig. S5 ).…”

Section: Resultsmentioning

confidence: 99%

“…We synthesized 2-substituted thiazolidine substrates according the Ershov et al. ( 41 ), specifically those derived from L-Cys ( Fig. 4 A and SI Appendix , Fig.…”

Section: Resultsmentioning

confidence: 99%

A flavin-dependent monooxygenase produces nitrogenous tomato aroma volatiles using cysteine as a nitrogen source

Liscombe

Kamiyoshihara

Ghironzi

et al. 2022

Proc. Natl. Acad. Sci. U.S.A.

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“…The synthesis yielded a mixture of diastereomers where aldehydes with electron‐rich rings favoured formation of the (2 S ,4 R ) isomer over the (2 R ,4 R ) isomer (10 : 1 ratio for 6 d , Table 2 ) based on comparison of chemical shifts with those published for similar structures. [42] In most of the cases the diastereomeric ratio was found to be between 1 : 1 to 4 : 1. Separation of the individual diastereomers was not carried out at this stage and all compounds were tested as mixtures.…”

Section: Resultsmentioning

confidence: 92%

An Experimental Toolbox for Structure‐Based Hit Discovery for P. aeruginosa FabF, a Promising Target for Antibiotics

et al. 2021

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FabF (3-oxoacyl-[acyl-carrier-protein] synthase 2), which catalyses the rate limiting condensation reaction in the fatty acid synthesis II pathway, is an attractive target for new antibiotics. Here, we focus on FabF from P. aeruginosa (PaFabF) as antibiotics against this pathogen are urgently needed. To facilitate exploration of this target we have set up an experimental toolbox consisting of binding assays using bio-layer interferometry (BLI) as well as saturation transfer difference (STD) and WaterLOGSY NMR in addition to robust conditions for structure determination. The suitability of the toolbox to support structure-based design of FabF inhibitors was demonstrated through the validation of hits obtained from virtual screening. Screening a library of almost 5 million compounds resulted in 6 compounds for which binding into the malonyl-binding site of FabF was shown. For one of the hits, the crystal structure in complex with PaFabF was determined. Based on the obtained binding mode, analogues were designed and synthesised, but affinity could not be improved. This work has laid the foundation for structure-based exploration of PaFabF.

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“…At m/z =132 and 115, base peaks could be seen. The molecular ion peaks were exhibited by the mass spectra of 4R)-diastereomer mixture is formed as the 2-Substituted thiazolidine-4carboxylic acids possess a chiral carbon atom [23], as shown in Fig. 2.…”

Section: Mass Spectramentioning

confidence: 97%

Synthesis, Antibacterial Activity and DFT Calculations of Some Thiazolidine-4-Carboxylic acid Derivatives and Their Complexes with Cu(II), Fe(II) and VO(II)

2020

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T HE reaction of L-Cysteine with 2-hydroxy naphthaldehyde and 2-hydroxy benzaldehyde yields novel bidentate ligands (2R,4R)-2-(2-hydroxynaphthalen-1-yl) thiazolidine-4carboxylic acid (L 2) and (2R,4R)-2-(2-hydroxyphenyl) thiazolidine-4-carboxylic acid (L 1), respectively, which can be characterised based on spectral and physical data. Synthesis of complexes with the formula ML 2 .XH 2 O is done via the reaction of L 1 and L 2 with Cu(II), Fe(II) and VO(II) in molar ratio of 1:2 pertaining to metal to ligand. Based on mass and UV/ visible spectra, IR, flame atomic absorption, magnetic susceptibility as well as thermal analysis of metal complexes, we can conclude that the ligands behave as a bidentate and help to identify proper structure pertaining to complexes. Then, screening of the synthesized compounds is carried out to determine their antibacterial activity against Pseudomonas aeruginosa and Streptococcus epidermis. All compounds showed bio-activity with iron complexes possessing the highest efficiency. The density functional theory at the B3LYP level of theory was employed to calculate the geometry optimisation pertaining to molecular structure as well as energies of ligands and its associated complexes. The observations of the theoretical calculations were in line with the outcomes of the experiment.

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Synthesis of 2-Substituted (2R,4R)-3-(3-Mercapto-Propionyl)Thiazolidine-4-Carboxylic Acids

Cited by 12 publications

References 16 publications

A flavin-dependent monooxygenase produces nitrogenous tomato aroma volatiles using cysteine as a nitrogen source

A flavin-dependent monooxygenase produces nitrogenous tomato aroma volatiles using cysteine as a nitrogen source

An Experimental Toolbox for Structure‐Based Hit Discovery for P. aeruginosa FabF, a Promising Target for Antibiotics

Synthesis, Antibacterial Activity and DFT Calculations of Some Thiazolidine-4-Carboxylic acid Derivatives and Their Complexes with Cu(II), Fe(II) and VO(II)

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