Synthesis, characterization and crystal structure of (2RS,4R)-2-(2-hydroxy-3-methoxyphenyl)thiazolidine-4-carboxylic acid

Muche, Simon; Müller, Mat­thias; Hołyńska, Małgorzata

doi:10.1016/j.molstruc.2017.10.090

Cited by 8 publications

(5 citation statements)

References 32 publications

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“…30 PLP upon reaction with cysteine exhibits two new peaks that appear at δ = 6.05 ppm and 6.10 ppm corresponding to the methine proton (z) of the racemic mixture of the thiazolidine ring formed with PLP and cysteine. 31 A third new peak (x) was observed at δ = 8.09 ppm which may correspond to the aldiminic proton of the Schiff base formed between PLP and cysteine. To confirm the position of the aldiminic proton, and thus the formation of Schiff base, PLP and Smethylcysteine (SMC), a cysteine analog that does not have a free thiol for ring closure, were reacted similarly.…”

Section: Resultsmentioning

confidence: 99%

Enzyme-Independent Interaction of Pyridoxal-5’-Phosphate with Cysteine

Mulay

Chen

Krishna

2022

Preprint

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Pyridoxal-5′-phosphate (PLP), commonly known as Vitamin B6, is a versatile co-factor that assists in different types of enzymatic reactions. PLP has also been reported to react with substrates and catalyze some of these reactions independent of enzymes. One such catalytic reaction is the breakdown of cysteine to produce hydrogen sulfide (H2S) in the presence of multivalent metal ions. However, the catalytic activity of PLP in catabolizing cysteine in the absence of multivalent ions is unknown. In this study, we show that, under physiological conditions and in the absence of enzymes and multivalent metal ions, PLP reacts with cysteine to form a thiazolidine product. The formation of a thiazolidine product is supported by quantum chemical simulation of the absorption spectrum. The reaction of PLP with cysteine is dependent on ionic strength and pH. The thiazolidine product slowly decomposes to produce H2S and the PLP regenerates to its active form with longer reaction times (>24 hours), suggesting that PLP can act as a catalyst. We have proposed an enzyme-independent plausible reaction mechanism for PLP-cysteine catalysis which proceeds through the formation of thiazolidine ring intermediates that later hydrolyzes slowly to regenerate the PLP. This work demonstrates that PLP catalyzes cysteine in the absence of (i) enzymes, (ii) base, and (iii) multivalent metal ions to produce H2S.

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Section: Resultsmentioning

confidence: 99%

Enzyme-Independent Interaction of Pyridoxal-5’-Phosphate with Cysteine

Mulay

Chen

Krishna

2022

Preprint

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“…S2 ) 23 . PLP upon reaction with cysteine exhibits two new peaks that appear at δ = 6.05 ppm and 6.10 ppm corresponding to the methine proton (z) of the racemic mixture of the thiazolidine ring formed with PLP and cysteine 24 . A third new peak (x) was observed at δ = 8.09 ppm which may correspond to the aldiminic proton of the Schiff base formed between PLP and cysteine.…”

Section: Resultsmentioning

confidence: 99%

Enzyme-independent catabolism of cysteine with pyridoxal-5′-phosphate

Mulay

Chen

Krishna

2023

Sci Rep

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Pyridoxal-5′-phosphate (PLP) is a versatile cofactor that assists in different types of enzymatic reactions. PLP has also been reported to react with substrates and catalyze some of these reactions independent of enzymes. One such catalytic reaction is the breakdown of cysteine to produce hydrogen sulfide (H2S) in the presence of multivalent metal ions. However, the enzyme-independent catalytic activity of PLP in catabolizing cysteine in the absence of multivalent ions is unknown. In this study, we show that PLP reacts with cysteine to form a thiazolidine product, which is supported by quantum chemical calculations of the absorption spectrum. The reaction of PLP with cysteine is dependent on ionic strength and pH. The thiazolidine product slowly decomposes to produce H2S and the PLP regenerates to its active form with longer reaction times (> 24 h), suggesting that PLP can act as a catalyst. We propose an enzyme-independent plausible reaction mechanism for PLP catalyzed cysteine breakdown to produce H2S, which proceeds through the formation of thiazolidine ring intermediates that later hydrolyzes slowly to regenerate the PLP. This work demonstrates that PLP catalyzes cysteine breakdown in the absence of enzymes, base, and multivalent metal ions to produce H2S.

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“…The thiazolidine derivatives were created using an enantioselective three‐component reaction employing chiral Cu(I)OTf, pybox (2,6‐bis((R)‐5,5‐ dibutyl‐4‐phenyl 4,5‐dihydrooxazol‐2‐yl) pyridine) complex, toluene, and imines 79 , alkynes 80 , and isothiocyanates 78 to synthesis [91] . Recently, L‐cysteine 81 and ortho‐vanillin 82 were used to create a racemic mixture of (2RS,4R)‐2‐(2‐hydroxy‐3‐methoxyphenyl) thiazolidine‐4‐carboxylic acid, which was then agitated at 80 °C for 10 minutes [92] . Thiazolidine‐2,4‐dione was produced by Asati et al.…”

Section: Discussionmentioning

confidence: 99%

“…[91] Recently, L-cysteine 81 and ortho-vanillin 82 were used to create a racemic mixture of (2RS,4R)-2-(2-hydroxy-3-methoxyphenyl) thiazolidine-4-carboxylic acid, which was then agitated at 80 °C for 10 minutes. [92] Thiazolidine-2,4-dione was produced by Asati et al via the interaction of thiourea 7 and chloroacetic acid 83 in the presence of concentrated HCl. [93]…”

Section: Synthetic Routes For Thiazolidine Derivativesmentioning

confidence: 99%

Recent Studies of Nitrogen and Sulfur Containing Heterocyclic Analogues as Novel Antidiabetic Agents: A Review

Gharge,

Alegaon

2024

Chemistry & Biodiversity

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The prevalence of diabetes mellitus is on the rise, which demands for the identification of novel antidiabetic drugs. There is a need for safer and more effective alternatives because the therapy methods now available to manage diabetes have limits. Due to their diverse pharmacological characteristics, heterocyclic molecules with nitrogen and Sulfur atoms have become intriguing candidates in medicinal chemistry. These substances have a wide variety of structures that can be customized to target different pathways associated with diabetes and can affect important biological targets involved in glucose homeostasis. This review provides a thorough summary of the most recent studies on heterocyclic analogues of nitrogen and Sulfur as prospective antidiabetic agents. This review examines the variety of their structural forms, their methods of action, and assesses the results of preclinical and clinical investigations on their effectiveness and safety. Additionally, further optimization and development of innovative antidiabetic medications are highlighted, as well as the difficulties and prospects for the future in utilizing the therapeutic potential of these analogues. This study seeks to stimulate additional investigation and cooperation between researchers and medicinal chemists, promoting improvements in the creation of efficient and secure antidiabetic medicines to fulfil the needs in the management of diabetes.

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Synthesis, characterization and crystal structure of (2RS,4R)-2-(2-hydroxy-3-methoxyphenyl)thiazolidine-4-carboxylic acid

Cited by 8 publications

References 32 publications

Enzyme-Independent Interaction of Pyridoxal-5’-Phosphate with Cysteine

Enzyme-Independent Interaction of Pyridoxal-5’-Phosphate with Cysteine

Enzyme-independent catabolism of cysteine with pyridoxal-5′-phosphate

Recent Studies of Nitrogen and Sulfur Containing Heterocyclic Analogues as Novel Antidiabetic Agents: A Review

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