D-Tyrosine - Moligand™,≥98% , CAS No.556-02-5

CAS: 556-02-5 Cat. No.: T101403 Summenformel: C₉H₁₁NO₃ Molekulargewicht: 181.19 Beilstein Registry Number: 14605 EG-Nummer: 209-112-6

GRADE & PURITY Moligand™, ≥98%

Synonyms

CCRIS 7710 | myo-Inositol hexanicotinate | DB03839 | d-p-Tyrosine | (R)-2-Amino-3-(p-hydroxyphenyl)propionic acid | Q16082044 | 3-(4-Hydroxyphenyl)-D-alanine | C06420 | AS-11715 | (2R)-2-Amino-3-(4-hydroxyphenyl)propanoic acid; (R)-Tyrosine; D-p-Tyrosine

Storage

Room temperature

Shipped In

Normal

Übersicht

application：

D-Tyrosine is synthesized from phenylalanine. It is also the precursor of epinephrine, thyroid hormones, and melanin.

Specifications

Synonyme

CCRIS 7710 | myo-Inositol hexanicotinate | DB03839 | d-p-Tyrosine | (R)-2-Amino-3-(p-hydroxyphenyl)propionic acid | Q16082044 | 3-(4-Hydroxyphenyl)-D-alanine | C06420 | AS-11715 | (2R)-2-Amino-3-(4-hydroxyphenyl)propanoic acid; (R)-Tyrosine; D-p-Tyrosine

Spezifikationen & Reinheit

Moligand™,≥98%

Biochemische und physiologische Mechanismen

D-Tyrosine is the D-isomer of tyrosine. D-Tyrosine negatively regulates melanin synthesis by inhibiting tyrosinase activity. D-Tyrosine inhibits biofilm formation and trigger the self-dispersal of biofilms without suppressing bacterial growth.

Storage

Room temperature

Verschickt in

Normal

Note

Moligand™

Aktionsart

INHIBITOR

Reinheit

≥98%

Namen und Kennungen

• Pubchem Sid: 488184644
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488184644
• Kanonisches Lächeln: C1=CC(=CC=C1CC(C(=O)O)N)O
• IUPAC Name: (2R)-2-amino-3-(4-hydroxyphenyl)propanoic acid
• InChIKey: OUYCCCASQSFEME-MRVPVSSYSA-N
• INCHI: 1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m1/s1
• Isomere SMILES: C1=CC(=CC=C1C[C@H](C(=O)O)N)O
• Molekulargewicht: 181.19
• Beilstein: 14605
• Reaxy-Rn: 515881
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=515881&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Klasse Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Ebene5 Amino acids and derivatives
          • Ebene6 Alpha amino acids and derivatives
            • Ebene7 Tyrosine and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Klasse: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Tyrosine and derivatives
• Alternative Parents: Phenylalanine and derivatives Phenylpropanoic acids D-alpha-amino acids Amphetamines and derivatives Aralkylamines 1-hydroxy-2-unsubstituted benzenoids Amino acids Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Tyrosine or derivatives - Phenylalanine or derivatives - 3-phenylpropanoic-acid - Alpha-amino acid - Amphetamine or derivatives - D-alpha-amino acid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Aralkylamine - Monocyclic benzene moiety - Benzenoid - Amino acid - Carboxylic acid - Monocarboxylic acid or derivatives - Organic oxide - Organooxygen compound - Organonitrogen compound - Amine - Primary aliphatic amine - Organic nitrogen compound - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Hydrocarbon derivative - Primary amine - Aromatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as tyrosine and derivatives. These are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
• External Descriptors: Other amino acids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Zugehörige Ziele (menschlich)

CA2 Tclin Carbonic anhydrase II (17698 Activities)

Discover Target: CA2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA1 Tclin Carbonic anhydrase I (13240 Activities)

Discover Target: CA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC7A5 Tchem L-type amino acid transporter 1 (388 Activities)

Discover Target: SLC7A5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)

Discover Target: RGS4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

Discover Target: MEN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Zugehörige Ziele (nicht menschlich)

Carbonic anhydrase (69 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Staphylococcus aureus (210822 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slc16a10 Monocarboxylate transporter 10 (73 Activities)

Discover Target: Slc16a10

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Wirkungsmechanismen

Chemische und physikalische Eigenschaften

• Löslichkeit: Soluble in water
• Spezifische Drehung [α]: +10.3°, c = 5 in 1 M HCl
• Schmelzpunkt (°C): 310-314°C
• Molekulargewicht: 181.190 g/mol
• XLogP3: -2.300
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 181.074 Da
• Monoisotopic Mass: 181.074 Da
• Topological Polar Surface Area: 83.600 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 176.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referenzen

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2. Yang Li, Bingxuan Ji, Ziyang Chen, Zhenghua Zhang.  (2023)  Polydopamine and d-tyrosine-functionalized PTFE membrane for membrane distillation of secondary effluent: Fouling mitigation and mechanism.  JOURNAL OF MEMBRANE SCIENCE,      [PMID:] [10.1016/j.memsci.2023.121857]

3. Yuhe Shen, Dongshuang Jia, Yuefei Wang, Tao Yu, Xiaojian Xu, Heng Chang, Qing Li, Rongxin Su, Wei Qi.  (2023)  Enzymatic oxidation of tyrosine enantiomers into biomimetic pigments with enhanced performance for hair dyeing.  DYES AND PIGMENTS,      [PMID:] [10.1016/j.dyepig.2023.111360]

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8. Hongyi Li, Yifu Wang, Xinxin Zhao, Zhen Yan, Chao Song, Shuguang Wang.  (2023)  Chirality of tyrosine controls biofilm formation via the regulation of bacterial adhesion.  BIOCHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.bej.2023.108844]

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15. Xiaohui Niu, Simeng Yan, Letong Wang, Jinliang Chen, Rui Zhao, Hongxia Li, Jian Liu, Kunjie Wang.  (2022)  Induction of chiral polymers from metal-organic framework for stereoselective recognition.  ANALYTICA CHIMICA ACTA,      [PMID:35151404] [10.1016/j.aca.2022.339546]

16. Qingfang Niu, Pengyue Jin, Yu Huang, Lifang Fan, Caihong Zhang, Cheng Yang, Chuan Dong, Wenting Liang, Shaomin Shuang.  (2022)  A selective electrochemical chiral interface based on a carboxymethyl-β-cyclodextrin/Pd@Au nanoparticles/3D reduced graphene oxide nanocomposite for tyrosine enantiomer recognition.  ANALYST,  147  (5): (880-888).  [PMID:35137747] [10.1039/D1AN02262H]

17. Xiaohui Niu, Simeng Yan, Jinliang Chen, Hongxia Li, Kunjie Wang.  (2022)  Enantioselective recognition of L/D-amino acids in the chiral nanochannels of a metal-organic framework.  ELECTROCHIMICA ACTA,      [PMID:] [10.1016/j.electacta.2021.139809]

18. Jiao Zou, Guoqing Zhao, Jin-Feng Guan, Xinyu Jiang, Jin-Gang Yu.  (2021)  Single-Layer Graphene Oxide-Amino-β-Cyclodextrin/Black Phosphorus Nanosheet Composites for Recognition of Tyrosine Enantiomers.  ACS Applied Nano Materials,      [PMID:] [10.1021/acsanm.1c02847]

19. Jinglei Liu, Wenbo Yuan, Caifeng Li, Mengmeng Cheng, Yan Su, Lijian Xu, Tianfei Chu, Shifeng Hou.  (2021)  l-Cysteine-Modified Graphene Oxide-Based Membrane for Chiral Selective Separation.  ACS Applied Materials & Interfaces,      [PMID:34628847] [10.1021/acsami.1c14900]

20. Qianqian Zhao, Wenrong Cai, Baozhu Yang, Zheng-Zhi Yin, Datong Wu, Yong Kong.  (2021)  Electrochemiluminescent chiral discrimination with chiral Ag2S quantum dots/few-layer carbon nitride nanosheets.  ANALYST,  146  (20): (6245-6251).  [PMID:34528650] [10.1039/D1AN01437D]

21. Zhan Gao, Zhihao Yu, Xiaoli Zhang, Shougang Fan, Huiyu Gao, Caini Liu, Qixing Zhou, Huaiqi Shao, Lan Wang, Xiaoyan Guo.  (2021)  Exploration on Optimized Control Way of D-Amino Acid for Efficiently Mitigating Membrane Biofouling of Membrane Bioreactor.  Membranes,  11  (8): (612).  [PMID:34436375] [10.3390/membranes11080612]

22. Qianqian Zhao, Datong Wu, Zheng-Zhi Yin, Wenrong Cai, Haifeng Zhou, Yong Kong.  (2021)  Fluorometric discrimination of tyrosine isomers based on the inner filter effect of chiral Au nanoparticles on MoS2 quantum dots.  Analytical Methods,  13  (20): (2290-2296).  [PMID:33969836] [10.1039/D1AY00145K]

23. Liu Nijuan, Liu Jingjing, Niu Xiaohui, Wang Jia, Guo Ruibin, Mo Zunli.  (2021)  An electrochemical chiral sensor based on the synergy of chiral ionic liquid and 3D-NGMWCNT for tryptophan enantioselective recognition.  MICROCHIMICA ACTA,  188  (5): (1-13).  [PMID:33839948] [10.1007/s00604-021-04818-w]

24. Lamei Yang, Feng Luo, Weili Wei.  (2021)  Simultaneous determination of the concentration and enantiomeric excess of amino acids with a coumarin-derived achiral probe.  Analytical Methods,  13  (16): (1905-1910).  [PMID:33913945] [10.1039/D1AY00271F]

25. Jia Wang, Zunli Mo, Nijuan Liu, Ruibin Guo, Chao Shuai, Fang Chen, Yongxin Du, Jingjing Liu, Guigui Liu, Qibing Dong, Qinqin Gao, Ying Chen, Wentong Liu.  (2021)  Construction of electrochemical chiral interface of C3N4/Ppy/ self-assembled polysaccharide.  JOURNAL OF ELECTROANALYTICAL CHEMISTRY,      [PMID:] [10.1016/j.jelechem.2021.115118]

26. Zou Jiao, Lan Xi-Wen, Zhao Guo-Qing, Huang Zhao-Ning, Liu Yi-Ping, Yu Jin-Gang.  (2020)  Immobilization of 6-O-α-maltosyl-β-cyclodextrin on the surface of black phosphorus nanosheets for selective chiral recognition of tyrosine enantiomers.  MICROCHIMICA ACTA,  187  (11): (1-11).  [PMID:33141322] [10.1007/s00604-020-04606-y]

27. Jiao Zou, Jin-Gang Yu.  (2020)  Nafion-stabilized black phosphorus nanosheets-maltosyl-β-cyclodextrin as a chiral sensor for tryptophan enantiomers.  Materials Science & Engineering C-Materials for Biological Applications,      [PMID:32409064] [10.1016/j.msec.2020.110910]

28. Tingting Wang, Yuhuan Cheng, Yulian Zhang, Jinyin Zha, Jiannong Ye, Qingcui Chu, Guifang Cheng.  (2019)  β-cyclodextrin modified quantum dots as pseudo-stationary phase for direct enantioseparation based on capillary electrophoresis with laser-induced fluorescence detection.  TALANTA,      [PMID:31987180] [10.1016/j.talanta.2019.120629]

29. Huali Liu, Zhen Li, Yan Yan, Jiaqi Zhao, Yu Wang.  (2019)  Chiroptical study of the bimetal–cysteine hybrid composite: interaction between cysteine and Au/Ag alloyed nanotubes.  Nanoscale,  11  (45): (21990-21998).  [PMID:31710078] [10.1039/C9NR07421J]

30. Jiao Zou, Jin-Gang Yu.  (2019)  Chiral recognition of tyrosine enantiomers on a novel bis-aminosaccharides composite modified glassy carbon electrode.  ANALYTICA CHIMICA ACTA,      [PMID:31623714] [10.1016/j.aca.2019.08.018]

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32. Datong Wu, Wensheng Tan, Hongda Li, Zhangchen Lei, Linhong Deng, Yong Kong.  (2018)  A facile route to prepare functional mesoporous organosilica spheres with electroactive units for chiral recognition of amino acids.  ANALYST,  144  (2): (543-549).  [PMID:30411759] [10.1039/C8AN01519H]

33. Huang Lu, Li Yanxia, Lin Qi, Lou Benyong, Chen Yiting.  (2018)  Enantioselective permeations of amino acids through l-proline-modified gold nanochannel membrane: an experimental and theoretical study.  AMINO ACIDS,  50  (11): (1549-1556).  [PMID:30073606] [10.1007/s00726-018-2629-0]

34. Datong Wu, Wensheng Tan, Yin Yu, Baozhu Yang, Hongda Li, Yong Kong.  (2018)  A facile avenue to prepare chiral graphene sheets as electrode modification for electrochemical enantiorecognition.  ANALYTICA CHIMICA ACTA,      [PMID:30172332] [10.1016/j.aca.2018.06.029]

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36. Yin Yu, Yongxin Tao, Baozhu Yang, Datong Wu, Yong Qin, Yong Kong.  (2017)  Smart Chiral Sensing Platform with Alterable Enantioselectivity.  ANALYTICAL CHEMISTRY,      [PMID:29125282] [10.1021/acs.analchem.7b03783]

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42. Runqiu Nie, Xiangjie Bo, Huan Wang, Lijun Zeng, Liping Guo.  (2012)  Chiral electrochemical sensing for tyrosine enantiomers on glassy carbon electrode modified with cysteic acid.  ELECTROCHEMISTRY COMMUNICATIONS,      [PMID:] [10.1016/j.elecom.2012.11.014]

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44. Fangqin Wang, Wenrong Cai, Lilan Tan, Junyao Li, Datong Wu, Yong Kong.  (2024)  A Liquid–Liquid Interfacial Strategy for Construction of Electroactive Chiral Covalent–Organic Frameworks with the Aim to Enlarge the Testing Scope of Chiral Electroanalysis.  ANALYTICAL CHEMISTRY,      [PMID:38335728] [10.1021/acs.analchem.3c05744]

45. Haibo Chen, Yan Luo, Wenrong Cai, Laidi Xu, Junyao Li, Yong Kong.  (2024)  Colorimetric discrimination and spectroscopic detection of tyrosine enantiomers based on melamine induced aggregation of l-cysteine/Au nanoparticles.  TALANTA,      [PMID:38340415] [10.1016/j.talanta.2024.125758]

46. Qing Li, Congnan Wu, Jiaxing Zhang, Rongxin Su, Yuefei Wang, Wei Qi.  (2024)  Construction of chiral nanozymes with high enantioselectivity for visual detection via smartphone-based paper sensors.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.153326]

47. Xuemei Shang, Mei Yang, Tiantian Su, Junli Guo, Chenxi Zhao, Pei Song, Yan-Yan Song, Yucen Li.  (2025)  Modulation of Electron Transport via Target Recognition in Asymmetric Nanochannel Arrays for Enantiomer Detection.  ANALYTICAL CHEMISTRY,      [PMID:40600873] [10.1021/acs.analchem.5c02831]

48. Hongyu Li, Li Cen, Shiyu Liu, Ziqing Qiu, Yanfei Zhang, Xingyu Luo.  (2025)  Preparation of copper-based protein-inorganic hybrid nanoflowers with peroxidase-like activity for colorimetric detection of biothiols.  ANALYTICA CHIMICA ACTA,      [PMID:41093535] [10.1016/j.aca.2025.344685]

49. Jing Zhang, Ye Yang, Yi-Ping Liu, Guo-Cong Liu, Xi Zhu, Xin-Yu Jiang, Jin-Gang Yu.  (2025)  Highly selective and efficient recognition of tyrosine enantiomers at Au NPs/D-sorbitol/GCE-based chiral sensor.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2025.115424]

50. Zhe Wang, Zixiao Wang, Jiamin Wang, Yu He, Junping Wang.  (2025)  Novel electrochemical sensor with chiral recognition function prepared from N-CDs and cobalt-based nanomaterials for the detection of tyrosine enantiomers in food.  JOURNAL OF FOOD COMPOSITION AND ANALYSIS,      [PMID:] [10.1016/j.jfca.2025.108353]

51. Junyao Li, Nan Shi, Chen Jin, Laidi Xu, Yong Kong.  (2025)  Synthesis of chiral multi-hole polydopamine nanospheres for spectroscopic and electrochemical discrimination of tryptophan enantiomers.  JOURNAL OF ELECTROANALYTICAL CHEMISTRY,      [PMID:] [10.1016/j.jelechem.2025.119486]

52. Du Jinyan, Xu Na, Wang Chaofeng, Shu Qin, Xu Qidi, Zhang Ping, Zhuo Shujuan, Zhu Changqing.  (2022)  Red emission B, N, S-co-doped carbon dots with pH-responsive functionality for colorimetric and fluorescent dual-mode detection of Ag+ ions.  JOURNAL OF MATERIALS SCIENCE,  57  (47): (21693-21708).  [PMID:] [10.1007/s10853-022-07988-x]

53. Ma Xiaofei, Zhang Chengchen, Cai Liangliang.  (2022)  Functional ionic liquids as chiral selector for visual chiral sensing and enantioselective precipitate.  CHEMICAL PAPERS,  77  (1): (259-268).  [PMID:] [10.1007/s11696-022-02490-9]

54. Kun Yang, Ruyi Wang, Junjian Lu, Jin Wang, Xuewei Liao, Chen Wang.  (2024)  A covalent organic framework nanosheet-nanochannel composite with signal amplification strategy for electrochemical enantioselective recognition.  TALANTA,      [PMID:38823324] [10.1016/j.talanta.2024.126331]

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