HO - initiated oxidation of isoleucine amino acid in the aqueous phase

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The results showed that the overall diffusioncontrolled rate constant is equal to 4.82×109 M-1 s -1 at 298.15K. The zwitterionic form is the main existing form that plays an essential role in the HO - initiated oxidation of Ile (99.98%). The most preponderant reactions are found at C6-H (36.19%) and C8-H (37.77%) positions. Finally, the influence of temperature on the overall rate is also evaluated.

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Nội dung Text: HO - initiated oxidation of isoleucine amino acid in the aqueous phase

Cite this paper: Vietnam J. Chem., 2023, 61(S1), 37-44 Research article DOI: 10.1002/vjch.202200210 HO● - initiated oxidation of isoleucine amino acid in the aqueous phase Nguyen Thi Huong Lan1, Truong Dinh Hieu1,2, Ngo Thi Chinh1,2, Nguyen Thi Le Anh1,2, Pham Thi Yen Nhi2, Dao Duy Quang1,2,* 1 Faculty of Pharmacy, Duy Tan University, Da Nang 55000, Viet Nam 2 Institute of Research and Development, Duy Tan University, Da Nang 55000, Viet Nam Submitted; Revised; Accepted Abstract Protein damage by the direct oxidative attack on amino acid side chains is considered the main cause of human aging and diseases. Therefore, a better understanding of the oxidation process is necessary for screening and designing new drugs. In this work, the oxidation of L-isoleucine (Ile) by HO● radical was mechanistically and kinetically studied using M05-2X/6-311++G(3df,3pd)//M05-2X/6-311++G(d,p) level of theory. All possible hydrogen transfer (HT) and single electron transfer (SET) reactions are considered in the aqueous phase. The results showed that the overall diffusion- controlled rate constant is equal to 4.82×109 M-1s-1 at 298.15K. The zwitterionic form is the main existing form that plays an essential role in the HO● - initiated oxidation of Ile (99.98%). The most preponderant reactions are found at C6-H (36.19%) and C8-H (37.77%) positions. Finally, the influence of temperature on the overall rate is also evaluated. Keywords. Amino acid, oxidation, free radical, kinetics, DFT, hydrogen transfer, SET. 1. INTRODUCTION or a carboxylic acid, whereas the latter leads to the Fenton reaction-based production of hydroxyl radical Amino acids contain the amino (-NH2/NH3+) and or anion (HO• or HO−) that damages biomolecules. For carboxylic (-COOH/COO–) groups.[1] They are example, Schöneich[14] studied the reaction mechanism naturally abundant in humans, animals, plants, and of methionine (Met) oxidation by ROS. The results microorganisms. Currently, approximately 500 illustrated that Met donates one or two electrons natural amino acids have been identified.[2] Among depending on the ROS nature to form Met radical them, only 20 α-amino acids play the role of building cation or Met sulfoxide, respectively. Galano et al. blocks of proteins and are necessary for the normal computationally studied the HO•-initiated oxidation of physiological functions of cells.[3] All amino acids, asparagine (Asn)[15] and serine (Ser)[16] in the gas phase except for glycine, have the L-configuration in free at the B3LYP/6-311G(d,p) level of theory. The form.[4] Essential and non-essential amino acids are hydrogen transfer (HT) was identified to occur two main types of natural α-amino acids,[5] which exclusively from the beta site, and the overall play an important role in metabolism, temperature-dependent rate constants (koverall) are neurotransmitters, and intercellular signaling.[6] (5.50±0.25)×107 exp[(1482±13)/T] (Asn), and Oxidative damage of biomolecules like DNA, (3.91±0.17) × 108 exp[(1446±12)/T] (Ser) (Lmol-1s-1). lipids, and protein by reactive oxygen species (ROS) Another study by Galano et al.[17] showed that the has generally been involved in the pathogenesis of oxidation of Met by HO• radicals arises almost via HT several diseases, such as cancer, allergies, viral reaction at the gamma (γ) site. The overall infections, inflammation, atherosclerosis, and temperature-dependent rate constant at the neurodegeneration,[7,8] as well as certain physiological BHandHLYP/6-311G(d,p) level was k = processes (i.e., aging, ischemia-reperfusion injury, and (2.12±0.26)×107 exp[(2047±34)/T], (in Lmol-1 s-1). protein turnover).[9] The oxidation mechanism of α- Medina et al have thermo-chemically and kinetically amino acids has been attracting the attention of several investigated the reaction of a leucine derivative with works for decades.[10-14] The modification of free biological radicals, in both aqueous and lipid media.[18] amino acids and proteins might be related to ionizing Their results illustrate that the γ site of leucine was the radiation in the presence of oxygen or metal ion- most favorable for the reactions with •N3, •OOCCl3, catalyzed oxidation.[9] The first leads to the formation • OCH3, •OCH2Cl, and •OCHCl2 radicals in the aqueous of NH4+ and -keto acids, CO2, and either an aldehyde solution, showing rate constants of 1.97×105, 37 Wiley Online Library © 2023 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH
25728288, 2023, S1, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/vjch.202200210 by Readcube (Labtiva Inc.), Wiley Online Library on [01/05/2024]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License Vietnam Journal of Chemistry Dao Duy Quang et al. 3.24×104, 6.68×105, 5.98×106 and 8.87×108 M-1s-1, and zwitterionic forms (figures 1A and 1B). Sen et respectively. In another work, the HT and single- al.[27] investigated the kinetic and mechanistic electron transfer (SET) reactions between free radicals oxidative degradation of Ile by Au3+ complexes in a and a cysteine derivative were also kinetically and weak acid medium and then compared it with the ones thermodynamically investigated.[19] The most reactive of L-leucine. The results showed that L-isoleucine for the HT reactions was determined at the γ site of underwent oxidation more rapidly than L-leucine cysteine. Recently, Nathanael et al.[20] showed (Leu) with lower activation enthalpy and higher relatively high rate constants (4-7108 M-1s-1) for the negative activation entropy. reaction between NO3• radical with N-acylated proline So far, systematic evaluations of the Ile oxidation and N-methyl glycine residues in acetonitrile media. mechanism by hydroxyl (HO•) radical are limited. In L-(+)-isoleucine (Ile), is an important nutrient this study, the HO•-initiated oxidation of Ile was for physiological functions (i.e., growth, systematically evaluated by the density functional improvement of the immune system, protein theory (DFT) approach. Two mechanisms including metabolism, fatty acid metabolism, reducing blood single electron transfer (SET) and hydrogen transfer glucose and hepatic glucose levels).[19-23,24,27] The (HT) were considered in the aqueous phase. The human body cannot synthesize Ile, which must come thermodynamic parameters and kinetics of those from the diet.[3] In nature, Ile is generally found in reactions were calculated to shed light on the meat, fish, poultry, eggs, cheese, lentils, nuts, and oxidation mechanism. seeds.[26] The free Ile commonly exists in both neutral Figure 1: 2D-structure of isoleucine (Ile) amino acid in (A) neutral form, (B) zwitterionic form 2. COMPUTATIONAL METHOD The rate constants of two Ile oxidation reactions (i.e., hydrogen transfer (HT) and single electron Gaussian 16 Rev.A.03 package[28] was used for transfer (SET)) were calculated by the conventional optimizations of structure and calculations of transition state theory (TST) approach. The KiSThelP vibrational frequency for all species. We applied was employed to estimate the thermodynamic M05-2X functional[29] and the 6-311++G(d,p) basis equivalent as the following equation (eq.2):[43] set that has been widely used in many studies for −∆𝐺0,≠ (𝑇) 𝑘 𝑇 𝑅𝑇 ∆𝑛 kinetic calculations.[30-37] The M05-2X/6- 𝑘 𝑇𝑆𝑇 (𝑇) = 𝜎 ℎ ( 𝑃0 ) 𝑒 𝑅𝑇 𝐵 (2) 311++G(3df,3pd) level of theory was then employed where σ, kB, h, R, and T are respectively the reaction to calculate the accurate single-point energies. The path degeneracy, Boltzmann, Planck, molar gas optimal scaling factor for this method is determined constants, and temperature. ∆G‡ is the Gibbs free as 0.961.[38] The implicit solvation model based on energy of activation; Δn = 1 (bimolecular) or 0 density (SMD) was applied for the calculations in the (unimolecular). aqueous phase.[39] The ∆G‡ values of HT reactions were determined In solution, there is an equilibrium transformation by the Gibbs energy differences between reactants and between two forms of Ile via reaction (R1) (figure 1). the transition state (TS), whereas Marcus’s theory was The standard enthalpies (∆H0) and Gibbs free energies applied to calculate ∆G‡ of the SET reaction. [44,45] (∆G0) of this reaction were estimated as the energy In the KiSThelP, the tunneling correction factor differences between neutral and zwitterionic forms. was determined by the Wigner correction, χ(T) [43,46,47] The equilibrium constants – Kf[40-42] of reaction that was calculated based on the imaginary (R1) were then determined to value the percentage of frequency lm(v‡) of the transition states (TSs) as the each existing form in the solution based on the ΔrG0 following equation:[43] 2 as follows: 1 ℎ lm(𝑣 ‡ ) Δ 𝐺0 𝜒(𝑇) = 1 + 24 ( 𝑘𝑏 𝑇 ) (3) − r K𝑓 = 𝑒 𝑅𝑇 (1) The rate constant was estimated as follows: © 2023 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 38
25728288, 2023, S1, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/vjch.202200210 by Readcube (Labtiva Inc.), Wiley Online Library on [01/05/2024]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License Vietnam Journal of Chemistry HO● - initiated oxidation of isoleucine amino… 𝑘(𝑇) = 𝜒(𝑇) × 𝑘 𝑇𝑆𝑇 (𝑇) (4) 3. RESULTS AND DISCUSSION According to Collins-Kimball principle,[48] the 3.1. Structural and electronic properties apparent rate constant (kapp) needs to be estimated for the diffusion limit reactions equation (5). The structures of the neutral (A) and the zwitterionic (B) forms were optimized and shown in figure 2. In 𝑘𝐷𝑘 𝑘 𝑎𝑝𝑝 = (5) these structures, the C5 atoms link to –NH2 and 𝑘 𝐷 +𝑘 –COOH functional groups for the neutral form (A), and –NH3+ and –COO– ones for the zwitterionic form where k and kD are the thermal and steady-state (B). Besides, ΔH0 and ΔG0 values of the zwitterionic Smoluchowski[49] rate constants. form are both 4.9 kcalmol-1 lower than the ones of the Finally, the overall rate constant (koverall) was neutral Ile. Therefore, the neutral-to-zwitterionic estimated according to the (eq.6) based on the molar transformation reaction (figure 1) has a high stability fraction of neutral (fA) and zwitterionic (fB) forms: constant (Kf) being 3.75×103 at 298.15K. As a result, the zwitterionic form consists of the major form of Ile 𝑘 𝑜𝑣𝑒𝑟𝑎𝑙𝑙 = 𝑓 𝐴 × ∑ 𝑘 𝐴𝐻𝑇 + 𝑓 𝐴 × 𝑘 𝐴𝑆𝐸𝑇 + 𝑓 𝐵 × ∑ 𝑘 𝐵𝐻𝑇 + 𝑆𝐸𝑇 in the studied condition, accounting for 𝑓𝐵 × 𝑘 𝐵 (6) approximately 99.97%. In addition, the orbital structures HOMO and LUMO concentrate mainly at The branching ratio (Γ) for each reaction the O1, O2, C9, C5, and N3 positions. The ESP maps pathway[40,41] was determined as the (eq.7): illustrate that the negative charge density is found in 𝑓 𝑖 ×𝑘 𝑗 the carboxylic functional group for both forms. Γ𝑖,𝑗 = 𝑘 𝑜𝑣𝑒𝑟𝑎𝑙𝑙 × 100 (7) However, the density in the zwitterionic form is higher than that in the neutral one. Similarly, the SEAGrid (http://seagrid.org)[50-52] is positive charge concentrating at the –NH3+ group in acknowledged for computational resources and the zwitterionic form is remarkably higher than that services for the results presented in this publication. at the –NH2 group in the neutral form. Figure 2: Optimized structures, HOMO – LUMO, and ESP maps (-0.06 to 0.06 a.u.) of neutral (A) and zwitterionic (B) Ile (iso-value = 0.02). The numbering of all atoms is also shown. Red, blue, grey, and light grey balls represent oxygen, nitrogen, carbon, and hydrogen atom, respectively 3.2. Mechanism of HO• - initiated oxidation of HO● and the transferred H vary from 1.44 to 1.58Å. Furthermore, the C/N-H-O angles of the interactive The optimized structure of the transition states for the sites are from 131.0 to 178.8º. The imaginary hydrogen transfer process between HO● radical with frequencies of TSs are quite large, from 650i (for the neutral and zwitterionic forms of Ile are presented H13) to 1444i (for the H20 reaction). Multiple in figures 3 and 4, respectively. conformers of TSs are also found at some reactions As seen in figure 3, there are 17 possible reactive such as H10, H12, H16A, H17, and H18 positions sites on the neutral form where HO● radicals can which have quite different energies and imaginary attack. The C/NH bonds at TSs change from 1.05 to frequencies. Only the most stable TS structures were 1.17Å. Meanwhile, the distances between the O atom chosen for further reaction kinetics calculations. © 2023 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 39
25728288, 2023, S1, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/vjch.202200210 by Readcube (Labtiva Inc.), Wiley Online Library on [01/05/2024]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License Vietnam Journal of Chemistry Dao Duy Quang et al. Figure 3: Optimized transition states (TSs) for HT reaction between the neutral form and HO• radical calculated in the aqueous phase. Bond distances are in Å, and angles are in degrees. Values in parentheses are the imaginary frequencies (in cm-1) of TSs Figure 4: Optimized transition states (TSs) for HT reaction between the zwitterionic form and HO• radical calculated in the aqueous phase. Bond distances are in Å, and angles are in degrees. Values in parentheses are the imaginary frequencies (in cm-1) of TSs In the case of the HT reactions of the zwitterionic TSs vary from 145.2 to 179.2º. The imaginary form (figure 4), the C/NH bond distances are lower frequencies of TSs are from 581i (for H21) to 1522i than those of neutral forms, being 1.14 to 1.17Å, and (for H11), which allows for determining these real the distances between the O atom of HO● and the transition states. Multiple conformers of TSs are also transferred H atom are from 1.37 to 1.55Å. Besides, observed for the reactions at H10A, H12, H16, and it is observed that the N-H-O or C-H-O angles of the H17A positions. © 2023 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 40
25728288, 2023, S1, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/vjch.202200210 by Readcube (Labtiva Inc.), Wiley Online Library on [01/05/2024]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License Vietnam Journal of Chemistry HO● - initiated oxidation of isoleucine amino… 3.3. Reaction kinetics kinetics results for HT and SET reactions of the Tables 1 and 2 demonstrate thermochemistry and neutral and zwitterionic Ile with HO●, respectively. Table 1: The Gibbs free energy of reaction (ΔrG0, kcal mol-1), Gibbs free energy of activation ‡ (ΔG , kcal mol-1), Wigner correction (χ), diffusion rate constant (kD, M-1s-1), TST thermal rate constant (kT, M-1s-1), diffusion-corrected apparent rate constant (kapp, M-1s-1), and branching ratio (, %) for HT and SET between the neutral form and HO• obtained at 298.15K Position ΔrG0 ΔG‡ χ kD kT kapp  HT H10 -26.9 6.2 2.02 3.06×109 8.65×109 2.26×109 0.01 H11 -47.1 9.1 2.38 3.12×109 8.08×107 7.87×107 0.00 H12 -26.0 8.5 1.83 3.14×109 1.67×108 1.59×108 0.00 H13 -26.0 8.0 1.50 3.17×109 2.95×108 2.70×108 0.00 H14 -21.4 9.6 2.41 3.04×109 3.18×107 3.14×107 0.00 H15 -21.5 9.0 2.23 3.10×109 8.38×107 8.16×107 0.00 H16 -21.5 9.2 2.11 3.08×109 5.78×107 5.67×107 0.00 H17 -22.6 9.0 2.26 3.09×109 9.31×107 9.03×107 0.00 H18 -22.6 8.8 2.08 3.09×109 1.07×108 1.04×108 0.00 H19 -16.3 9.2 2.02 3.10×109 5.40×107 5.31×107 0.00 H20 -22.3 9.4 2.85 2.81×109 5.99×107 5.86×107 0.00 H21 -22.3 8.3 1.62 2.78×109 2.21×108 2.05×108 0.00 SET 11.1 12.7 – 8.04×109 8.06×104 8.06×104 0.00 Total 3.48×109 0.02 Table 2: The Gibbs free energy of reaction (ΔrG0, kcal mol-1), Gibbs free energy of activation ‡ (ΔG , kcal mol-1), Wigner correction (χ), diffusion rate constant (kD, M-1s-1), TST thermal rate constant (kT, M-1s-1), diffusion-corrected apparent rate constant (kapp, M-1s-1), and branching ratio (, %) for HT and SET between the zwitterionic form and HO• obtained at 298.15K Position ΔrG0 ΔG‡ χ kD kT kapp  HT H10 -6.2 7.3 1.62 3.15×109 1.06×109 7.91×108 16.41 H11 -26.2 11.3 3.03 2.99×109 2.27×106 2.27×106 0.05 H12 -25.6 6.8 2.09 3.13×109 3.43×109 1.64×109 33.96 H13 -25.6 8.3 1.55 3.18×109 1.11×108 1.07×108 2.23 H14 -21.1 8.4 2.26 3.08×109 2.49×108 2.30×108 4.78 H15 -21.1 8.5 2.53 3.11×109 2.32×108 2.16×108 4.48 H16 -21.1 10.0 2.19 3.09×109 1.47×107 1.47×107 0.30 H17 -22.4 6.8 2.45 3.09×109 3.96×109 1.74×109 36.01 H18 -22.4 9.2 2.12 3.10×109 5.66×107 5.56×107 1.15 H19 -22.4 9.6 2.06 3.13×109 2.95×107 2.92×107 0.61 H21 -23.4 28.2 1.34 2.87×109 4.52×10-7 4.52×10-7 0.00 SET 24.7 25.9 – 8.00×109 1.54×10-5 1.54×10-5 0.00 Total 4.82×109 99.98 The results presented in tables 1 and 2 showed relatively low, from 6.2 to 9.6 kcal mol-1 (neutral Ile) that all HT reactions are spontaneous, showing and 6.8 to 11.3 kcal mol-1 (zwitterionic Ile), except a greatly negative ΔrG0 values of -47.1 to -16.3 high ∆G‡ value of 28.2 kcal mol-1 for the reaction at kcal mol-1 (neutral Ile) and -26.2 to -6.2 kcal mol-1 the H21 of zwitterionic form. As a result, the apparent (zwitterionic Ile). The most negative ΔrG0 for the HT rates constants (kapp) are almost very high and close to reactions with HO● of both forms is obtained at the the diffusion limit, being from 3.14×107 to 2.26×109 H11 site. Furthermore, the ∆G‡ for these reactions are M-1s-1 for neutral form and from 2.27×106 to 1.74×109 © 2023 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 41
25728288, 2023, S1, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/vjch.202200210 by Readcube (Labtiva Inc.), Wiley Online Library on [01/05/2024]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License Vietnam Journal of Chemistry Dao Duy Quang et al. M-1s-1 for zwitterionic one, except for the negligible to have the value of 3.56×109 M-1s-1 at 350K. Thus, value obtained at the H21 site being 4.52×10-7 M-1s-1. the HO● - initiated Ile oxidation arises at the fastest In addition, the kapp values of HT reactions are rate at average human biological temperature. 3.48×109 (neutral Ile) and 4.82×109 M-1s-1 In summary, the HO●-initiated oxidation reaction (zwitterionic form). of Ile gets the highest rate constant (4.99×109 M-1s-1) The SET reactions are unfavorable, with at the average human body temperature (310K). A considerably positive values of ΔrG0 (11.1 and 24.7 relatively high rate constant at 298.15K (4.82×109 kcal mol-1) and ∆G‡ (12.7 and 25.9 kcal mol-1). M-1s-1) is also determined. Thus, the HT reactions of Indeed, the SET rate constants being 8.06×104 zwitterionic form with HO● showed as the (neutral form) and 1.54×10-5 M-1s-1 (zwitterionic predominant pathway (99.98%). form) are much lower than that of HT reactions. Thus, the koverall for the Ile-HO● reaction is determined as 4. CONCLUSIONS 4.82×109 M-1s-1 which is 4 times higher than that obtained for the L-leucine -HO● reaction (koverall: In this work, the HO● - initiated oxidation of 1.18×109 M-1s-1) at the same level of theory.[37] isoleucine (Ile) was investigated in water using the Regarding the branching ratios (Γ), the HT DFT approach. The kinetics of HT and SET reactions reactions for the neutral form showed Γ values from for both neutral and zwitterionic forms were 0.00% to 0.01%, and the total value is only 0.02% calculated in detail. Several observations are as owing to the low molar fraction of the neutral form follows: (0.03%) as mentioned above. Oppositely, the ones of - The zwitterionic form (99.97%) is the major Ile the zwitterionic form are high, varying from 0.05 (at form in the biological medium. the H11 site) to 36.01% (at the H17 site), except for the - HT reactions are favorable and spontaneous, Γ at the H21 position being 0.00%. The Γ total value with a koverall of 4.82×109 M-1s-1 at 298.15K. The HT for these reactions is 99.98%. The Γ values for SET reaction between the zwitterionic form and HO● reactions of both forms are negligible, roughly 0.00%. radical is dominant with a branching ratio (Γ) of Additionally, the major products of the HT reaction are 99.98%. Besides, the main HT products of found at the H12, and H13 sites of the methylene group zwitterionic are found at the C6-H (34.93%) and C8- (at C6), and the H17, H18, and H19 positions of the H positions (34.55%). methyl group (at C8) of zwitterionic form, with the - The highest rate constant, 4.99×109 M-1s-1, is total Γ being 36.19 and 37.77%, respectively. determined at the average temperature of the human Moreover, figure 5 shows the temperature effect body (310K). (from 290 to 350K) on the rate constant (k) for the Ile oxidation by HO● radical. It is observed that the Acknowledgments. This research is funded by reaction rate increases from 290 to 310K before Vietnam National Foundation for Science and decreasing as a function of the temperature up to 350 Technology Development (NAFOSTED) under grant K. At 290K, the rate constant is determined as number 103.01-2019.380. This work used the 4.07×109 M-1s-1. This value remarkably rises to reach Extreme Science and Engineering Discovery a peak of 4.99×109 M-1s-1 at 310K, which is the Environment (XSEDE), which is supported by the average human body temperature. After that, the National Science Foundation grant number OCI- oxidation rate decreases as a function of temperature 1053575. Conflict of interest. The authors declare no conflict of interest. REFERENCES 1. S. Kaya, B. Tüzün, C. Kaya, I. B. Obot. Determination of corrosion inhibition effects of amino acids: quantum chemical and molecular dynamic simulation study, J. Taiwan Inst. Chem. Eng, 2016, 58, 528-535. 2. I. Wagner, H. Musso. New naturally occurring amino acids, Angew. Chem., Int. Ed., 1983, 22, 816-828. 3. M. A. Gruca, D. L. Dufour. Essential amino acid, in: Int. Encycl. Bio. Anthropol., 2018, 1-2. Figure 5: Rate constant (k) as a function of 4. G. Wu. Amino acids: metabolism, functions, and temperature (290 to 350K) nutrition, Amino Acids, 2009, 37, 1-17. © 2023 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 42
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