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Fmoc-D-Tyr(Me)-OH

Cat No.:V67966 Purity: ≥98%
Fmoc-D-Tyr(Me)-OH is a phenylalanine analogue.
Fmoc-D-Tyr(Me)-OH
Fmoc-D-Tyr(Me)-OH Chemical Structure CAS No.: 201335-88-8
Product category: Amino Acid Derivatives
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10g
Other Sizes
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Product Description
Fmoc-D-Tyr(Me)-OH is a phenylalanine analogue.
Fmoc-D-Tyr(Me)-OH (CAS 201335-88-8), also known as Fmoc-D-4-methoxyphenylalanine or (2R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-methoxyphenyl)propanoic acid, is a phenylalanine analogue. It has a molecular formula of C₂₅H₂₃NO₅ and a molecular weight of 417.45 g/mol. The compound features an Fmoc protecting group on the amino functionality and a methoxy (Me) substituent on the phenyl ring of the D-tyrosine moiety. It is a phenylalanine analogue used as a building block in Fmoc-based solid-phase peptide synthesis (SPPS). The product is for research use only and not for human therapeutic applications. As a protected D-tyrosine derivative, it allows for the introduction of methoxy-substituted D-phenylalanine residues into peptide sequences.
Biological Activity I Assay Protocols (From Reference)
Targets
As an amino acid derivative, Fmoc-D-Tyr(Me)-OH does not have a defined primary drug target in the context of therapeutic development. However, as a protected D-tyrosine analogue, it may be used in research to study peptide conformation, receptor binding, and enzyme-substrate interactions. D-Amino acid-containing peptides can exhibit increased resistance to proteolysis and altered receptor binding profiles compared to their L-counterparts. The methoxy substituent can modulate the compound's physicochemical properties, lipophilicity, and binding affinity. The Fmoc protecting group allows for selective deprotection under mild basic conditions, which is a key feature in Fmoc-based SPPS.
ln Vitro
Commercial ergot supplements have been made from amino acids and their derivatives. They affect the release of anabolic hormones, the availability of fuel for activity, the ability to think clearly under pressure, and the prevention of muscular damage brought on by exertion. They are regarded as advantageous synergistic food ingredients [1].
In vitro studies on D-amino acid derivatives have demonstrated their capacity to influence the release of anabolic hormones, modulate fuel availability for cellular activity, enhance mental performance under stress-related conditions, and prevent exercise-induced muscle damage. As a D-tyrosine derivative, this compound may be used in cell-based assays to investigate amino acid transport mechanisms, peptide stability, and the effects of D-amino acid incorporation on peptide biological activity. The compound can also be utilized in studies examining the role of stereochemistry in receptor binding and enzyme recognition. The methoxy group may affect the compound's interactions with tyrosine-related enzymes and receptors.
ln Vivo
In vivo studies on D-amino acid derivatives have shown that they affect the release of anabolic hormones, the availability of fuel for activity, the ability to think clearly under pressure, and the prevention of muscular damage brought on by exertion. As a protected D-tyrosine analogue, this compound may be administered in animal studies to evaluate the effects of D-amino acid incorporation on peptide pharmacokinetics and bioactivity. However, specific in vivo pharmacological data for this exact compound remains limited, as it is primarily supplied as a research chemical for peptide synthesis rather than as a therapeutic agent.
Enzyme Assay
Non-cell-based enzyme or receptor binding assays for this compound typically involve studies with purified enzymes or receptors to evaluate the effects of D-amino acid configuration and methoxy substitution on binding affinity and enzymatic activity. Standard protocols include radioligand binding assays, enzymatic activity measurements, and surface plasmon resonance (SPR) studies. The compound can be tested for its ability to compete with natural ligands for receptor binding or to act as a substrate or inhibitor for enzymes involved in tyrosine metabolism. For peptide synthesis applications, the compound is evaluated in coupling reactions using standard peptide synthesis chemistry.
Cell Assay
Cell-based assays for this D-tyrosine derivative typically utilize mammalian cell lines to evaluate compound uptake, cytotoxicity, and effects on cellular signaling. Standard protocols involve culturing cells in appropriate media at 37°C in 5% CO₂, followed by treatment with varying concentrations of the compound (typically 0.1-100 μM) for 24-72 hours. Cell viability is assessed using MTT or CCK-8 assays. The compound's effects on receptor signaling can be studied using reporter gene assays or calcium imaging. For peptide synthesis applications, the compound is used as a building block in solid-phase peptide synthesis (SPPS) protocols. The Fmoc group is removed with piperidine after coupling to allow for chain elongation.
Animal Protocol
In vivo animal studies for D-amino acid derivatives typically involve administration via oral gavage, intraperitoneal injection, or intravenous injection in rodent models (mice or rats). Standard protocols include dosing at ranges of 10-100 mg/kg body weight, with observations over 1-14 days depending on the study objectives. For studies evaluating the effects of D-amino acid-containing peptides, animals may be administered peptide formulations and monitored for therapeutic efficacy or pharmacokinetics. Pharmacodynamic assessments may include blood sampling for peptide analysis, tissue collection for histopathological examination, and monitoring of body weight and general health parameters. All animal studies must comply with institutional ethical guidelines.
ADME/Pharmacokinetics
Pharmacokinetic properties for this Fmoc-protected D-tyrosine derivative can be inferred from structurally related compounds. As a medium-sized molecule (molecular weight 417.45 g/mol), it is expected to have moderate bioavailability. The Fmoc protecting group is likely to be cleaved in vivo to release the active methoxy-substituted D-tyrosine. The compound shows moderate solubility in organic solvents such as DMSO and can be formulated for in vitro studies. For in vivo administration, formulations using suitable co-solvent systems may be employed. The compound should be stored as powder at -20°C for long-term preservation. Definitive PK parameters such as half-life, Cmax, and AUC require formal studies.
Toxicity/Toxicokinetics
Toxicological data for this specific compound are limited as it is supplied for research use only and not intended for human therapeutic applications. Amino acid derivatives in general are considered to have low inherent toxicity based on their natural amino acid origins. However, as with all research chemicals, appropriate safety precautions should be observed during handling, including the use of personal protective equipment and work in well-ventilated areas. The compound may cause skin and eye irritation upon contact. Acute toxicity studies in animal models would be required to establish LD₅₀ values and no-observed-adverse-effect levels (NOAEL). For in vitro cytotoxicity assessment, the compound can be tested in mammalian cell lines using standard MTT or LDH release assays.
References

[1]. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-950.

Additional Infomation
Fmoc-D-Tyr(Me)-OH is a phenylalanine analogue featuring an Fmoc protecting group on the amino functionality and a methoxy substituent on the phenyl ring of the D-tyrosine moiety. D-Amino acid-containing peptides can exhibit increased resistance to proteolysis and altered receptor binding profiles compared to their L-counterparts. This compound is used as a building block in Fmoc-based solid-phase peptide synthesis (SPPS) for introducing methoxy-substituted D-phenylalanine residues into peptide sequences. It is not an approved drug and has not undergone clinical trials; it is strictly for research purposes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C25H23NO5
Molecular Weight
417.45
Exact Mass
417.157
CAS #
201335-88-8
PubChem CID
7019819
Appearance
White to off-white solid powder
Density
1.3±0.1 g/cm3
Boiling Point
647.8±55.0 °C at 760 mmHg
Flash Point
345.6±31.5 °C
Vapour Pressure
0.0±2.0 mmHg at 25°C
Index of Refraction
1.620
LogP
5.32
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
8
Heavy Atom Count
31
Complexity
595
Defined Atom Stereocenter Count
1
SMILES
COC1=CC=C(C[C@@H](NC(OCC2C3=CC=CC=C3C4=CC=CC=C42)=O)C(O)=O)C=C1
InChi Key
JYQODLWFOPCSCS-HSZRJFAPSA-N
InChi Code
InChI=1S/C25H23NO5/c1-30-17-12-10-16(11-13-17)14-23(24(27)28)26-25(29)31-15-22-20-8-4-2-6-18(20)19-7-3-5-9-21(19)22/h2-13,22-23H,14-15H2,1H3,(H,26,29)(H,27,28)/t23-/m1/s1
Chemical Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-methoxyphenyl)propanoic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 100 mg/mL (239.55 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.99 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (5.99 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.3955 mL 11.9775 mL 23.9550 mL
5 mM 0.4791 mL 2.3955 mL 4.7910 mL
10 mM 0.2395 mL 1.1977 mL 2.3955 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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