N-Acetyl-L-tyrosine
(Synonyms: N-乙酰-L-酪氨酸) 目录号 : GC33802
An active metabolite of, and precursor to, L-tyrosine
Cas No.:537-55-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
N-acetyl-L-Tyrosine (NAT) is an active metabolite of, and precursor to, L-tyrosine.1,2 Dietary administration of NAT increases B. mori larvae heat stress tolerance and A. mellifera survival in a model of environmental stress.2 Blood levels of NAT are increased during heat and restraint stress in mice, and dietary administration of NAT decreases blood lipid peroxidation and corticosterone levels in a mouse model of restraint stress. Dietary administration of NAT also decreases tumor volume in an HCT116 mouse xenograft model. Urinary excretion of NAT is increased in patients with phenylketonuria (PKU) or tyrosinemia, inborn errors of amino acid metabolism characterized by mutations in the gene encoding phenylalanine hydroxylase (PAH) and a deficiency in fumarylacetoacetate hydrolase (FAH), the final enzyme in tyrosine catabolism, respectively.1 Formulations containing NAT have been used for amino acid supplementation in parenteral nutrition for preterm infants.
1.Jellum, E., Horn, L., Thoresen, O., et al.Urinary excretion of N-acetyl amino acids in patients with some inborn errors of amino acid metabolismScand. J. Clin. Lab. Invest. Suppl.18421-26(1986) 2.Matsumura, T., Uryu, O., Matsuhisa, F., et al.N-acetyl-L-tyrosine is an intrinsic triggering factor of mitohormesis in stressed animalsEMBO Rep.21(5)e49211(2020)
| Cas No. | 537-55-3 | SDF | |
| 别名 | N-乙酰-L-酪氨酸 | ||
| Canonical SMILES | OC1=CC=C(C=C1)C[C@@H](C(O)=O)NC(C)=O | ||
| 分子式 | C11H13NO4 | 分子量 | 223.23 |
| 溶解度 | DMSO : 44mg/mL | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.4797 mL | 22.3984 mL | 44.7968 mL |
| 5 mM | 0.8959 mL | 4.4797 mL | 8.9594 mL |
| 10 mM | 0.448 mL | 2.2398 mL | 4.4797 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
N-Acetyl-3,5-dibromo-l-tyrosine hemihydrate
Acta Crystallogr Sect E Struct Rep Online 2012 Sep 1;68(Pt 9):o2601-2.PMID:22969507DOI:10.1107/S1600536812032928.
The title compound, C(11)H(11)Br(2)NO(4)·0.5H(2)O, was prepared by an electrophilic bromination of N-Acetyl-L-tyrosine in acetonitrile at room temperature. The two independent mol-ecules do not differ substanti-ally and a mol-ecule of water completes the asymmetric unit. The synthesis of the title compound does not modify the stereochemical center, as shown by the absolute configuration found in this crystal structure. Comparison with the non-bromo starting material differs mainly by rotation features. For instance the H(methine)-C(chiral center)-C(methyl-ene)-C(ipso) is 173.0 (2)° torsion angle in one mol-ecule and 177.3 (2)° in the other, indicating a trans arrangement. This is in contrast with approximately 50° in the starting material. A short inter-molecular Br⋯Br separation is observed [3.2938 (3) Å]. The molecules in the crystal are connected via a network of hydrogen bonds through an N-H⋯O hydrogen bond between the hydroxy group of the phenol of the tyrosine and the N-H of the amide of the other molecule and an O-H⋯O hydrogen bond between the hydroxy group of the carboxylic acid and the oxygen of the carbonyl of the amide.
N-Acetyl-L-tyrosine is an intrinsic triggering factor of mitohormesis in stressed animals
EMBO Rep 2020 May 6;21(5):e49211.PMID:32118349DOI:10.15252/embr.201949211.
Under stress conditions, mitochondria release low levels of reactive oxygen species (ROS), which triggers a cytoprotective response, called "mitohormesis". It still remains unclear how mitochondria respond to stress-derived stimuli and release a low level of ROS. Here, we show that N-Acetyl-L-tyrosine (NAT) functions as a plausible intrinsic factor responsible for these tasks in stressed animals. NAT is present in the blood or hemolymph of healthy animals, and its concentrations increase in response to heat stress. Pretreatment with NAT significantly increases the stress tolerance of tested insects and mice. Analyses using Drosophila larvae and cultured cells demonstrate that the hormetic effects are triggered by transient NAT-induced perturbation of mitochondria, which causes a small increase in ROS production and leads to sequential retrograde responses: NAT-dependent FoxO activation increases in the gene expression of antioxidant enzymes and Keap1. Moreover, we find that NAT represses tumor growth, possibly via the activation of Keap1. In sum, we propose that NAT is a vital endogenous molecule that could serve as a triggering factor for mitohormesis.
N-Acetyl-L-tyrosine (NAT) as a substrate for mushroom tyrosinase
Pigment Cell Res 1998 Feb;11(1):24-33.PMID:9523332DOI:10.1111/j.1600-0749.1998.tb00707.x.
N-acetyl tyrosine (NAT) is hydroxylated by mushroom tyrosinase and the N-acetyl dopa formed is oxidized by the enzyme to N-acetyl dopaquinone (lambda max = 390 +/- 10 nm). H2O2 and NH2OH each shortened the lag period of NAT hydroxylation by the enzyme. H2O2 had an effect on the changes with time in the spectrum of product(s) formed and on the spectrum of the final product(s) obtained when NAT was hydroxylated by mushroom tyrosinase, in a manner suggesting that H2O2 converts N-acetyl dopaquinone to a pink-violet product(s) (lambda max = 490 nm), whereas such a product(s) was not formed in the absence of H2O2. A pink-violet product(s) (lambda max 490 +/- 20 nm) was also formed when NAT was hydroxylated by mushroom tyrosinase in the presence of NH2OH or para amino benzoic acid (PABA), probably as a result of an interaction between N-acetyl dopaquinone and NH2OH or PABA forming mono- or di-oximes. Kojic acid (5-hydroxy-2-hydroxymethyl)-4H-pyran-4-one) inhibited effectively the rate of NAT hydroxylation by mushroom tyrosinase in the absence or presence of H2O2. When NAT was oxidized by the enzyme in the absence of kojic acid, N-acetyl dopaquinone was formed at once and a shoulder at 490-530 nm appeared later. Under identical conditions but in the presence of kojic acid, a yellow product(s), characterized by a peak at 320 +/- 10 nm, was detected, suggesting that N-acetyl dopaquinone oxidizes kojic acid to the yellow product(s). Maltol (3-hydroxy-2-methyl-4H-pyran-4-one), a gamma-pyrone derivative structurally related to kojic acid, also inhibited the rate of NAT hydroxylation by mushroom tyrosinase. The addition of maltol at the plateau phase of the reaction resulted in an immediate decline in absorbance at 400 nm, suggesting that maltol conjugates with N-acetyl dopaquinone, yielding a product(s) characterized by a lower extinction coefficient at 400 nm than that of N-acetyl dopaquinone alone. The final brown-red product(s) formed when NAT was hydroxylated by mushroom tyrosinase was bleached in the presence of ascorbic acid or H2O2.
N-Acetyl-L-tyrosine as a tyrosine source during total parenteral nutrition in adult rats
Pediatr Res 1985 Jun;19(6):514-8.PMID:3925425DOI:10.1203/00006450-198506000-00002.
The tyrosine content of parenteral solutions is limited by poor tyrosine solubility. N-Acetyl-L-tyrosine has excellent solubility and is a potential source of intravenous tyrosine. Infusion of N-acetyl-U-14C-L-tyrosine as part of a total parenteral nutrition regimen in the rat at a level of 0.5 mmol/kg/day resulted in rapid labeling of tissue tyrosine pools, production of 14CO2, incorporation of 14C-labeled tyrosine into protein, and modest urinary losses (8.3%). Plasma tyrosine levels, however, remained at fasting values (73.8 +/- 5.40 microM). Infusion of N-Acetyl-L-tyrosine at 2 mmol/kg/day increased plasma tyrosine above fasting levels (141 +/- 16.1 microM), resulted in a rapid labeling of tissue tyrosine pools, production of 14CO2, and incorporation of 14C-labeled tyrosine into protein. However, urinary losses were higher (16.8%). Rapid utilization of N-Acetyl-L-tyrosine was noted at both infusion levels. Plasma- and tissue-free tyrosine pools were rapidly labeled, as was tissue protein. Radioactivity incorporated in tissue protein was shown to be tyrosine after acid hydrolysis.
Utilization of N-Acetyl-L-tyrosine and glycyl-L-tyrosine during long-term parenteral nutrition in the growing rat
Am J Clin Nutr 1985 Oct;42(4):585-96.PMID:3931451DOI:10.1093/ajcn/42.4.585.
Utilization of N-Acetyl-L-tyrosine and glycyl-L-tyrosine as a source of tyrosine in infusion solutions was tested in rats receiving total parenteral nutrition for 4 wk. The four solutions tested were isonitrogenous and isocaloric. One of the solutions contained an adequate amount of L-phenylalanine; in the other three, two-thirds of the phenylalanine was replaced by a corresponding amount of either glycine, glycyl-L-tyrosine or N-Acetyl-L-tyrosine. No differences in weight gain or N-balance could be detected as a result of administering either the solution with glycyl-L-tyrosine or with N-Acetyl-L-tyrosine in place of the solution containing an adequate phenylalanine content. The solution in which two-thirds of the L-phenylalanine was replaced by glycine yielded only half of the weight gain and correspondingly reduced values for N-balance. Daily urinary excretion rates for N-Acetyl-L-tyrosine and glycyl-L-tyrosine were 11% and 0.5%, respectively, of the infused amount. Plasma amino acid pattern was affected differently by the four solutions. The results indicate that both N-Acetyl-L-tyrosine and glycyl-L-tyrosine are efficiently utilized by the rat during total parenteral nutrition.