Efficient conversion of glutamic acid to healthy protein like thiomide with lycopene as catalyst using catalytic transfer sulfurization process

doi:10.21203/rs.3.rs-4345703/v1

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Efficient conversion of glutamic acid to healthy protein like thiomide with lycopene as catalyst using catalytic transfer sulfurization process

https://doi.org/10.21203/rs.3.rs-4345703/v1

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This paper describes a simple one-step catalytic transfer sulfurization technique that may be used to synthesize glutamic thiamides with the aid of lycopene. First, lycopene is made from fresh tomatoes using a solvent extraction technique, and it is then utilized to make the glutamic thiomides. Glutamic thiamide particles are characterized by Raman, FTIR, XRD, SEM and EDS. The lycopene acted as a catalyst for sulfurizing of glutamic acid in H₂S atmosphere. According to Image J analysis, the average size of the glutamic thiomide enclosed by lycopene is estimated to be in the range of 30 nm - 10 nm, respectively. When lycopene or H₂S are heated to 100°C for 45 min, lycopene shows 81.9 % catalytic activity in the conversion of glutamic acid to glutamic thiomide, and 89.2% with selectivity. Lycopene alone demonstrates 35.68% catalytic activity in the conversion of glutamic acid to glutamic thiomide with ethanol for the reaction time 15min. Moreover, lycopene-100 is stable and exhibits high catalytic efficiency in the decomposition of glutamic acids using various polar solvents.

hydrocarbon

water

protein

thiomides

lycopene

catalytic process

thermal conversion

selectivity

Amino acids are essential for the synthesis of hormones, neurotransmitters, and proteins [1]. These need to be altered in order to improve metabolism and general health [2–3]. Its alteration is intended to be accomplished by the sulfurization process. Traditionally, it has used high pressure and an excess of sulfur from fossil fuels; this is often an uncontrollable process that yields an excessive amount of sulfur products [4]. One kind of sulfur that occurs naturally is hydrogen sulfide. For catalytic transfer sulfurization over appropriate catalysts, hydrogen sulfide can be utilized as a green sulfur source [5–6]. It is discovered to be a more favored approach in the pharmaceutical sector.

Hydrocarbons have received a lot of attention recently because of their large surface area and brief diffusion pathway, which allow bulk transport to enhance catalytic performance. Additionally, these hydrocarbons feature hierarchically porous structures and designed porosity [7–8]. Improved acidity, increased p-donor capacities from carbon species, and greater acid-base tolerance are characteristics of mesoporous carbohydride, and lycopene in particular [9]. Lycopene can also be utilized to easily add and modify porosity, achieve optical transparency, fortify antimicrobial defenses, and achieve chemical and thermal stability. In a variety of organic processes, non-precious metal catalysts aided by lycopene have previously demonstrated promising results [10–12].

Optimized lycopene has multifunctional, distributed active sites that solvents may readily reach, which can greatly improve the material's catalytic performance and mitigate problems [13–14]. We describe the synthesis of lycopene and its application as a catalyst in the production of amino thiomides. The active sites, presented in the catalyst are highly efficient for coupling H₂S desulfurization in the catalytic transfer sulfurization of amino products. Additionally, lycopene can separate the basic species from the amino medium, preventing leaching or poisoning of amino groups (-NH₂⁻).

A kind of amino thiomides called glutamic thiomides is mostly used as a brain fuel to improve memory and mental clarity as well as a building block for proteins [15–17]. Until now, a variety of methods have been used to synthesize amino thiomide; these methods have been proven through expensive operations (volcanic operatus), which require a high temperature (> 100°C), a lot of poison products (CH₄, NH₃, and sulfur products), or the aid of a particular atmosphere (e.g., homolysis of water) [18–20]. Lycopene is a highly effective catalyst that catalyzes the conversion of amino acids to amino thiomides. Its activity is on par with that of the best catalysts based on precious nonmetals.

2.1 Materials & Methods

Glutamic acid, acetone, hexane, ethanol 98%, and diethyl ether were purchased from chemitech with purities of 95% above. Acetonitrile and methanol were purchased from sigma aldrich. Deionized water was used all through the experiments. All reagents were of analytical grade except of acetonitrile and methanol, which are chromotomographically pure. Food samples were purchased in local stores and finely ground and homogenised before analysis.

Scanning electron microscope is used to know the surface morphology of Lycopene and amino products. The powder X-ray diffraction patterns of Glutamic thiomide is acquired with a Bruker AXS D8 Advance diffractometer with Cu Kα (λ = 1.5418 Å) operating at 40 kV/40 mA. The data were collected from 2θ = 20° to 70°. Raman measurement is done with a Horiba Scientific Raman (model Labram HR, λ = 532 nm, hole = 100 µm) using different objectives. The concentration of the amino products after degradation was recorded using a UV-Vis spectrometer (ocean optics USB4000-UV-VIS, India).

2.2 Preparation of lycopene

The tomato samples were protected from the action of both light and oxygen in the air in order to prevent them from damaging the color. All steps were performed in subdued lighting at room temperature. Tomatoes were purchased in a grocery store. Individual tomatoes were sliced and all parts of it were utilized. The tomato was cut into approximately 1.5 cm cubes. Fresh tomato samples (500 g) were minced in a high speedy mill for around 5 min, or until the chunks were smaller than 4 mm. Fresh tomatoes were diluted 1:1 (w:v) in deionized water before blending. This produced well-homogenized tomato sauce, which was then heated at boiling for 20 min in the darkness. The hot suspension was then subjected to vacuum filtration for 30 minutes at 30 Hg pressure using a dynamic solid-liquid extractor. This particular procedure is intended to separate the most polar fraction and make tomato product more suitable for successive steps of extraction. Tomato paste has a moisture content of roughly 16% when the water is extracted using vacuum filtration. This mixture was to be homogenized and the tomato paste was to be filtrated as the next step in the extraction process.

The tomato paste was put in a waring blender together with acetone (1:1 w/v). Three times, the extraction was done under vacuum, and each time it took around 15 min. The water was almost entirely removed in the first two phases, and the moisture residue was removed in the third step. The final product consisted of two parts: a yellow-colored filtrate that was thrown away and a reddish-violet solid residue that comprised powder granules. Furthermore, the tomato paste was extracted three times for around 5 min each time using diethyl ether (1:1 w/v), producing a white residue with powdered granules. The ether appeared red in color and was heated to 40°C to eliminate the organic phase.

2.3 Catalytic transfer sulfurization process

It was carried out in a catalytic chamber that had a hot plate, glass plate, and an H₂S gas cylinder. Initially, 0.6 mg lycopene and 0.076 gr of glutamic acids are combined, and the mixture is exposed to H₂S gas for 45 min. The mixture was heated to 100°C before being exposed in order to soften the atom-to-atom bonds. During catalytic transfer sulfurization, amino compound and H₂S gas molecules are adsorbed over lycopene, which also maintains the molecules' constant interaction. The gauge meter has been used to track the H₂S gas flow rate, which was calculated to be about 10 MP/min.

Figure 1 provides a schematic representation of radical pairing as a function of temperature, solvent polarity, and reaction time. Initially (in Zone I), it seems that the reaction is not found to happen between the amino product and H₂S molecules, Since the amino product is a very large molecule and the reactive site is completely blocked off by other parts of the H₂S molecule. Sometimes, there may be a lot of collisions, but only the ones that occur at the reactive site have any chance of leading to less chemical reaction. When the temperature is applied, amino molecules absorb energy and speed up in response to thermal energy, which raises the possibility that they will react or collide. Thus, small fragments of glutamic acid and H₂S can produce free radicals such as HS^• and amalate, respectively (As shown in Zone II). As this is going on, the H and ^•OH combine to form water molecules. A certain amount of produced water molecules was able to escape through the cavities of closed chamber. Whatever water vapor was left would split into hydroxyl radicals (^•OH), which could take up hydrogen from H₂S and form mercapto (HS^•) radicals [21]. We employed lycopene as a catalyst to increase the conversion of amino product even further. H₂S molecules could be adsorbed on lycopene surface, where they would subsequently thermally break down into free radical species like H^•, S^•, and C^•. The glutamic molecule's carbonyl atoms would be drawn to the highly electronegativity free radical species (H^• and S^•) that would be produced [22]. Similarly, additional amino molecules may move from the suspension to the surface of the lycopene and subsequently transform into glutamic thiomides, water, and other gases. Catalyst recovery occurs when the small molecules derived from amino and H₂S molecules desorbed from the catalyst surface.

Additionally, a solvent may interact or coordinate with the catalyst to activate or deactivate it, as well as affect the catalyst's selectivity. The water/alcohol is believed to facilitate the lycopene by direct coordination and the subsequent formation of H-bond interactions with SH₂ (Fig. 1). The amount to which a radicalized lycopene pairs with related H₂S radicals can be adjusted by a solvent, and this can change the catalytic activity. Typically, in polar solvents like water (as shown in Zone III), the radical species tend to be highly solvated and the carbon and sulfur group radicals are usually completely separated from each other, allowing catalysis to proceed without the hindrance of the counter-ion. On the other hand, in low polarity solvents such as ethanol (as demonstrated in Zone IV), the counter-radical can block the lycopene active site, or cover the vacant coordination site where the CH₂ and H₂S group radicals would normally bind, forming a strong radical pair that can inhibit catalytic activity. There have been good correlations found between the type of radical pairing and catalytic activity.

Raman spectra of glutamic thiomide include lycopene in the solid state at ambient conditions are shown in Fig. 2 (a). The Raman spectra of lycopene have been assigned to C = C in-phase stretching, C-C stretching, and methyl in-plane rocking modes, respectively, and are located at 1520 cm^− 1, 1158 cm^− 1, and 1010 cm^− 1 [23]. The existence of SH stretching modes in the 2300–2700 cm^− 1 regions, as shown in Fig. 2(a), validates the sulfurization effect. The three separate peaks, which are centered at 2462 cm^− 1, 2662 cm^− 1, and 2986 cm^− 1, are caused by the stretching vibrations of SH⋯O, SC⋯N = O, and SC⋯NH₂, respectively [24]. Two distinct peaks can be found at 500 cm^− 1 and 960 cm^− 1, respectively, in Fig. 2(a). These peaks are the result of SH⋯O and SH⋯S vibrations. The difference between glutamic thiomide @ lycopene and individual glutamic thiomide molecules is observed over a wider range of wave numbers and vibrational frequencies. This is attributed to the increased interactions in hybrids. In glutamic thiomide@ lycopene, the SH⋯O band is red shifted and suppressed in intensity relative to unmodified glutamic thiomide due to interaction with LP in addition to water molecules. When compared to the unmodified glutamic thiomides shown in Fig. 2 (a), the SC⋯NH₂ band remains unchanged, while the new SC-CH₂ band appears at 2342 cm^− 1 due to coordination with sulfurized lycopene. These bands indicate that the sulfur-amino group has been restored following the reaction with lycopene, as the lack of any shift in the SC⋯NH₂ band [25].

The infrared peaks of glutamic thiomide are displayed in Fig. 2(b) at 3437.2, 2961.1, 2548, 1645.1, 1445.8, 1316.0-1000, 1080, and 751.3-677.8 cm^− 1. These correspond to the aromatic C-H bending vibration and the N-H, C-H (benzene ring), C-S, C-C, N-C (the C of benzene ring), -S-, and N-C (the C attached to S). The IR spectra of glutomic thiomide exhibit a similar spectral blue shift, which is caused by a decrease in the yield of glutamic thiomide molecules [26–28], due to the fact that the yield of a vibrating molecule is inversely proportional to the oscillation frequency. Therefore, bigger wave numbers, higher vibration frequencies, and lighter yields. In order to maintain a steady reaction time, lycopene was added to the recognized amino precursor in thiomides. Because the sum of the (R-S-R + -CH₂-R) groups results in a sulfuro methyl group around 1267 cm^− 1 band in the modified glutamic thiomide. However, upon the addition of lycopene, the position of the thiomide peaks do not change, but the variation in the intensity compared to unmodified glutamic thiomide. A rise in peak intensity in lycopene modified glutamic thiomide indicates an increase in the amount (per unit volume) of the functional group associated with the molecular bond.

EDS is used to determine the surface composition of glutamic thiomide compounds. Four elements of glutamic thiomide molecules like carbon (0.25 KeV), nitrogen (0.4 KeV), oxygen (0.55 K1 eV), and sulfur (2.5 KeV) had their EDS peaks deconvoluted. During the catalytic process, which lasted for 15 minutes at 100°C, we fixed the EDS spectra of glutamic thiomide molecule (Fig. 3) with the percentages of four species: carbon (100%), oxygen (25–65%), nitrogen (2–15%), and sulfur (5–10%). The coordination of carbon atoms in carboxylic/methyl groups with sulfur containing H₂S, which may be partially retained during the sulfurization process, could be the cause of the presence of sulfur in either the glutamic thiomide molecule or the glutamic thiomide lycopene molecule. The carbon EDS peak intensity of glutamic thiomide molecule become constant when glutamic product embedded with lycopene membrane indicates that carbon species of amino product might be not involved in the catalytic transfer sulfurization process. Meanwhile, glutamic-thiomide@lycopene exhibits a considerable decrease in oxygen contents from 33–20.5% when compared to glutamic-thiomide. This suggests that non-stable oxygen atoms were partially removed during the reaction between the glutamic acid and the lycopene polymer. Similar to glutamic-thiomide, glutamic-thiomide@lycopene exhibits a little increase in salfur percentage, which is explained by the presence of additional active sites on the carbon skeleton of the amino product. The elemental mapping of glutamic-thiomide@lycopene (Fig. 3) shows that oxygen, and sulfur species distribute homogeneously over the mesoporous hidrocarbon, with good spatial overlap of carbon, nitrogen, oxygen, and sulfur elements. The distinct configuration consisting of arranged mesoporous carbon encircled by hydrogen atoms may promote electron transfer, inhibit amino group leaching, and enhance the catalytic stability and activity of the resulting product [29].

As can be seen in the middle of Fig. 4, a SEM image demonstrates that glutamic thiomide nanoparticles are implanted in a lycopene. It also demonstrates that macro channels are cyclically aligned throughout sizable domains. SEM pictures of glutamic thiomide@lycopene demonstrate that lycopene layer may contain a cluster of amino molecules that make up -NH₂-, -H₃C = O, or H₂S molecules, as seen in the Fig. 4. Large lycopene particles (~ 20 nm) and ultrasmall nanoclusters (~ 5 nm) are effectively confined within the lycopene particles in these channels. The inside surface, which has several naturally occurring nano sized pores throughout, opens the active sites to interact chemically with the produced sulfur atoms, while the hollow shell can be employed as a template to physically absorb the adjacent H₂S molecules. By adding interconnected mesopores to macrochannels, more charge carriers are held, which facilitates the interaction of amino acids with H₂S molecules. Actually, the macrochannels served as a mass-transfer pathway for bringing incident H₂S flux into the inner surface of amino molecules in the macro-mesoporous channels of lycopene, which resulted in a notable improvement in the catalytic process.

The size distribution of various glutamic thiomide products, is seen in Fig. 5. According to Fig. 5, the average size of the glutamic thiomide enclosed by lycopene is approximately in the range of 30 nm − 10 nm, respectively. The glutamic thiomide particles were found to be much smaller than the lycopene particles, as the illustration indicated in the Figure (5). It has been observed that the mean size of the thiomide particle reduces as increase the reaction time. It has been attributed that the lycopene surface has uniformly distributed glutamic thiomide particles embedded in it. The lycopene contains channels made up of mesopores, which can give more particle harvesting and a high surface area for particle adsorption, resulting in a notable decrease in the mean size amino products.

The optical absorption spectra of the glutamic thiomides based on the laboratory conditions is shown in Fig. 6. The intensity of the maximum absorption peak of the glutamic thiomide reduced gradually with time and other factors. It can also be noted that the maximum wavelength of absorption was changed from 323.5 nm to 286.2 nm and 278.1 nm after reaction durations of 15 min and 45 min, respectively. The blue shifts of the absorption wavelength revealed the catalytic conversion of the glutamic acids. Eventually, the unique absorption peak became wide and weak in intensity, indicating the catalytic transferization of glutamic acids.

Figure 6 the change in absorbance spectra of glutamic thiomide for various laboratory conditions, revealing 58.9%, conversion in presence of thermal decomposition of lycopene and H₂S for 45 min, respectively. The concentration of the glutamic acid in the catalytic process experiment is 0.076 gr and dosage of the lycopene is 0.6 mg.

Table 1 presents the effectiveness of temperature, reaction time, and catalyst in the catalization of glutamic acid using H₂S as the sulfur agent. When no temperature or H₂S is added, no glutamic acid transformation would occur. When using H₂S as the sulfur source, temperature involvement shows a distinct difference in activity. For instance, H₂S at room temperature gives only 19.9% glutamic conversion and 22.56% glutamic-thiomide selectivity. As the temperature applied, glutamic acid conversion increases evidently for H₂S at temperature 100, which yields 27.3% conversion along with 29.1% glutamic-thiomide selectivity.

In the glutamic acid catalytic method, we also included two more control variables, such as catalyst and reaction time. One is lycopene, acted as catalyst under the same conditions, performed better in the glutamic acid conversion, suggesting that its mesoporous shape helps the substrate reach the active sites and increase catalytic activity. Lycopene-ethanol, when used as a solvent, yields a glutamic acid conversion of just 28.68%, suggesting that ethanol activates lycopene less effectively and dissociates more quickly than molecular H₂S to provide adsorbed sulfur atoms needed for the sulfurization of glutamic acid. Subsequently, we examined how the presence of water as a solvent affected the reaction rate. For example, 59.6% glutamic conversion and 64.2% glutamic-thiomide selectivity are obtained when lycopene and water are combined. Water is a cheap, environmentally benign green solvent. Both the simple diffusion impact of organic molecules in hierarchically porous structures and the activity of macrochannels as mass transport paths for injecting H₂S flux onto the inner surface of amino molecules can be linked to the increase of the selectivity. Reaction time is another important factor for the catalytic reaction [30–31], while the H₂S flow rate, reaction temperatures and reagent concentrations keep almost constant. As the reaction period increases from 15 to 45 min, there is a noticeable increase in glutamic acid conversion for lycopene water, with a conversion rate of 71.9% and glutamic -thiomide selectivity of 89.2%.

Table 1

shows the effect of temperature, reaction time, and catalyst on amino acid catalytic parameters in H₂S gas atmosphere.
Organic compound	(Hydrocarbon)Catalyst	Time	Advantage/drawbacks	yield/Selectivity	particle size	Ref
Glutamic acid	RT + WO LP	15	Easy way to prepare the nanoparticles and also conversion	19.9% /22.5%	30.7 nm	present
Glutamic acid	100⁰C + WOt LP	15	It is very flexible to prepare the qualitatively nanoparticle	27.3/29.1%	28.1 nm
Glutamic acid	100⁰C with LP contain EOH	15	Economically very feeble method to prepare nanoparticles qualitatively and quantitatively	35.68%/41.53%	25.4 nm
Glutamic acid	100⁰C with LP contain H₂O	15	It is convenient route for the preparation and conversion of acid particle to thiomide nanoparticle	59.6% /64.2%	21.5 nm
Glutamic acid	100⁰C with LP contain H₂O	30	Simple, cost effective and environmentally friendly	63.3/68.2	17.8 nm
Glutamic acid	100⁰C with LP contain H₂O	45min	Simple, cost effective and environmentally friendly	81.9 /89.2	15.5 nm	present
Indigenous bacteria	Extracellular polymeric substances (EPS)	9h	Expensive reagents, Ultrasonicator, bacteria, Incubator, long treatment/procedure	75.93		[32]
domestic sewage	polydimethylsiloxane	7–14 days	Need compressor, gas valves and pressure gauges, flow rate controller, Require several steps like biofilm formation, replacement acclimation, and stable operation	70–85%	0.31µm-176µm	[33]
acetaminophen	Azadirachta indica induced zinc oxide	30		25.28		[34]
	UiO-66-NH2/CS/mixed cellulose				220 nm	[35]
	PLA nonwoven filter		diesel oil, soybean oil, N-hexane, styrene, silicone oil Nheptane, silicone oil		10–100 µm	[36]
	CNF-PDA-coated cellulose acetate membrane				167.7 nm	[37]
Particulate organic carbon (POC) from municipal wastewater	microscreen coupled with a primary sedimentation	1h	Require several apparatuses like grit and grease chamber, equalization tank for transferring waste water, Turbidity meters and electromagnetic flowmeters, different designed pumps, large spaced camber	50 and 90%	15–20 µm	[38]
	Modified Chitosan– Gelatin membrane				100–200µm	[39]
	PPy@FP and PPy@CA-50 membrane				0.3608 µm	[40]
hexane and tetrachloromethane	Advanced PLA non-woven fabric			86.9%	∼25 µm	[41]
domestic sewage	PVDF	14days	High energy consumption, liquid fertilizer used, which resulted in the problem of storage	55		[42]
	Polymer	14days	“	40		[43]
	PTFE	14 days	“	20		[44]
Chemical oxygen demand (COD), phenol	membrane bioreactor (MBR)	20–60 days	Huge Experimental setup with several type of tools for operating reactor, low biodegradability, high operating time, low adsorption capacity	98% for COD, 70% for phenol,		[45]
Textile dyes	Magnetic GO	60		62		[46]
Textile dyes	rGO/MnO₂	60		84		[47]
PEI15-16	Polyetherimide			PEI15/15.33–57.76% and PEI16/74.76–81.42%		[48]
RFR	TiO₂-embedded PVDF membranes		TiO₂ nanoparticles with a low tendency of aggregation yielded the lowest fouling tendency	14.69%/78.24%	0.047 µm, 0.058 µm, and 0.032 µm	[49]
TSS, TDS	Polyamide			TSS − 20.00% and TDS − 29.87%		[50]

To assess the encapsulation effect by assessing the crystalline characteristics, XRD measurements (Fig. 6) were made directly on the surface of catalyzed products. Glutamic acid molecules are represented by the typical peaks at 23.7^◦ and 20.5^◦, respectively. Additionally, the composites with 2θ values at 23.6^°, 25.5^°, 26.1^°, 27.0^°, 28.1^°, and 31.2^° showed the crystalline form of sulfur (S8), which may be related to the reaction of S₂⁻ and SCO₂⁻ in the catalytic sulfurization process that was observed of sulfur atoms in thiomides. As stated in references [51–52], the amino groups were seen to exhibit peaks at 2θ values in the range of 35–40^◦. Glutamic thiomides are confirmed to belong to the orthorhombic crystal structure with space group P212121 and point group 222 based on the X-ray diffraction pattern [53]. The XRD spectra of Glutamic thiomides at various reaction times are displayed in Fig. 6. When the heating duration is increased from 15 min to 45 min, the reflections progressively shift to higher 2θ values. All of the diffraction peaks show fewer significant changes in peak locations and intensities as the heating period increases from 30 to 45 minutes, suggesting that the structural order of thiomides has reached saturation. The diffraction peaks at 22–26° were visible, indicating that lycopene was fully entrenched in the mixture of lycopene and thiomide [54].

In this work, we have shown the synthesize of lycopene nanoparticles using a deep eutectic solvent aided extraction approach in a simple and environmentally friendly way. The lycopene nanoparticles in their produced form were utilized as a helpful and efficient catalyst to initiate the reaction between amino and gaseous molecules when heat energy was applied. In the thermal breakdown of H₂S gas as the sulfurizing agent, the lycopene heated to 100^°C particles were found to exhibit extraordinary catalytic activity for sulfurizing glutamic acids, resulting in the formation of glutamic thiomide with 89% selectivity, respectively. In contrast, due to significantly fewer active sites on their surface, amino acids alone could only provide extremely weak sulfurization (< 25% conversion) in the absence of lycopene. The reaction mechanism and potential pathway were proposed. A greater amount of S and H radicals may have been thermally created as a result of the production of the mediated radicals ^•OH and ^•HS on the surface of lycopene through the thermal breakdown of water and H₂S. These radicals may then have reacted to form amino acid precursor aldehydes, which may have gone through the homolysis process to form amino thiomides. The size distribution from Image J analysis demonstrated that the mean size of glutamic thiomide@lycopene nanostructures is found to be in the range of 10nm to 30nm.

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Acknowledgements

This work was supported by Madanapalle Institute of Technology and Science

Authors' contributions

Martha Ramesh contributed for literature survey and writing this article

Ravoori Nagaraju contributed in plotting the figures of this article

A Santhosh kumar contributed in the organization the article

Ravuri Venkateswara Rao also contributed in reviewing this work

P Ramana reddy contributed in checking the similarity of this work

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No competing interests reported.

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Efficient conversion of glutamic acid to healthy protein like thiomide with lycopene as catalyst using catalytic transfer sulfurization process

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Abstract

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1 Introduction

2 Experimental

2.1 Materials & Methods

2.2 Preparation of lycopene

2.3 Catalytic transfer sulfurization process

3 Results & Discussions

Conclusions

Declarations

References

Additional Declarations

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