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Fmoc-Lys(Dde)-OH

Cat No.:V35887 Purity: ≥98%
Fmoc-L-Lys(Dde)-OH is a lysine analogue.
Fmoc-Lys(Dde)-OH
Fmoc-Lys(Dde)-OH Chemical Structure CAS No.: 333973-51-6
Product category: Peptides
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1g
Other Sizes
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Product Description
Fmoc-L-Lys(Dde)-OH is a lysine analogue.
Fmoc-Lys(Dde)-OH (Nα-[(9H-Fluoren-9-ylmethoxy)carbonyl]-Nε-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-lysine, CAS 333973-51-6) is an orthogonally protected derivative of the amino acid L-lysine. It features a 9-fluorenylmethyloxycarbonyl (Fmoc) group protecting the α-amino group and a Dde (1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl) group protecting the ε-amino group. With a molecular formula of C₃₁H₃₆N₂O₆ and a molecular weight of approximately 532.63 g/mol, this compound is a building block in Fmoc-based solid-phase peptide synthesis (Fmoc SPPS). The Dde group is an orthogonal protecting group that can be selectively removed under mild conditions (2% hydrazine in DMF), allowing for the synthesis of branched or labeled peptides.
Biological Activity I Assay Protocols (From Reference)
Targets
Fmoc-Lys(Dde)-OH does not have a specific biological target. Its primary utility is as a chemical building block in organic synthesis, particularly in Fmoc-based peptide synthesis. The compound serves as a protected lysine unit that can be incorporated into peptide chains while the Fmoc and Dde groups protect the α-amino and ε-amino groups, respectively, from unwanted reactions. Lysine is an essential amino acid involved in protein synthesis and post-translational modifications, but in its protected form, the compound is not designed to interact with biological receptors or enzymes. Its value lies in its chemical properties as a synthetic intermediate, enabling the construction of complex peptides and pharmaceutical compounds.
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].
Fmoc-Lys(Dde)-OH does not exhibit pharmacological activity in vitro. As a protected amino acid derivative, it is a synthetic intermediate rather than a bioactive compound. In vitro studies using this compound focus on its chemical reactivity, such as its use in peptide bond formation reactions and selective deprotection strategies, rather than assessments of pharmacological activity. The compound may be used as a substrate in enzymatic assays to study the cleavage of protecting groups, but these are analytical applications rather than pharmacological assessments. The compound does not bind to receptors, inhibit enzymes, or produce cytotoxic effects in cell-based assays at concentrations typically used for synthesis. Its role in research is almost exclusively as a reagent for organic synthesis.
ln Vivo
Fmoc-Lys(Dde)-OH is not a pharmacologically active compound and therefore does not have defined in vivo activity as a drug. When administered to animals, the compound would likely be metabolized to release lysine, which would then enter normal metabolic pathways. However, the compound is not used therapeutically, and its in vivo effects would be limited to those of the released lysine. Its primary value remains in synthetic chemistry, where it serves as a building block for the preparation of peptides and pharmaceutical compounds.
Enzyme Assay
In vitro assays for Fmoc-Lys(Dde)-OH are primarily focused on its chemical properties and reactivity rather than biological activity. Standard protocols in Fmoc-based solid-phase peptide synthesis involve the use of this compound as an orthogonally protected lysine building block. The compound is typically dissolved in polar aprotic solvents such as DMF or DCM and coupled to a growing peptide chain on a solid support using standard peptide coupling reagents such as HATU, HOBt, or DIC. The progress of the coupling reaction can be monitored by HPLC or TLC. The Fmoc group can be removed under basic conditions (e.g., 20% piperidine in DMF), and the Dde group can be selectively removed with 2% hydrazine in DMF, enabling the synthesis of branched or labeled peptides.
Cell Assay
In vitro cellular assays using Fmoc-Lys(Dde)-OH are not commonly performed because the compound lacks intrinsic biological activity. The compound is used exclusively in synthetic chemistry applications and is not designed for cell culture studies. Its use is confined to the laboratory, where it serves as a building block for the preparation of peptides and pharmaceutical compounds.
Animal Protocol
In vivo animal studies with Fmoc-Lys(Dde)-OH are not typically conducted, as the compound is a synthetic intermediate rather than a pharmacologically active agent. If used in vivo, the compound would be administered to animals to study the metabolism of protected amino acid derivatives. However, such studies are rare, and the compound is generally used exclusively in synthetic chemistry applications. Its use is confined to the laboratory, where it serves as a building block for the preparation of peptides and pharmaceutical compounds.
ADME/Pharmacokinetics
Fmoc-Lys(Dde)-OH is not a drug candidate, and pharmacokinetic data are not available. As a protected amino acid derivative, it is designed for chemical synthesis rather than systemic administration. If administered in vivo, the compound would likely be metabolized to release lysine. The compound's pharmacokinetic properties have not been characterized, and its use is confined to in vitro synthetic applications.
Toxicity/Toxicokinetics
The compound is generally considered to have low toxicity, consistent with its use as a chemical reagent. The compound is classified with hazard statements H302, H312, H315, H319, H332, and H335. Standard laboratory safety precautions, including the use of personal protective equipment, are recommended. Inhalation, ingestion, or skin contact should be avoided.
References

[1]. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144.

Additional Infomation
Fmoc-Lys(Dde)-OH (Nα-[(9H-Fluoren-9-ylmethoxy)carbonyl]-Nε-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-lysine, CAS 333973-51-6) is an orthogonally protected amino acid derivative used as a building block in peptide synthesis. Its chemical formula is C₃₁H₃₆N₂O₆ and molecular weight is approximately 532.63 g/mol. The compound features an Fmoc-protected α-amino group and a Dde-protected ε-amino group. It is intended for research use only and is not for human therapeutic applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C31H36N2O6
Molecular Weight
532.6273
Exact Mass
532.257
CAS #
333973-51-6
PubChem CID
135404832
Appearance
White to off-white solid powder
Density
1.2±0.1 g/cm3
Boiling Point
750.1±60.0 °C at 760 mmHg
Melting Point
-80ºC (dec.)
Flash Point
407.5±32.9 °C
Vapour Pressure
0.0±2.6 mmHg at 25°C
Index of Refraction
1.582
LogP
4.67
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
11
Heavy Atom Count
39
Complexity
964
Defined Atom Stereocenter Count
1
SMILES
O([H])C1=C(/C(/C([H])([H])[H])=N/C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]([H])(C(=O)O[H])N([H])C(=O)OC([H])([H])C2([H])C3=C([H])C([H])=C([H])C([H])=C3C3=C([H])C([H])=C([H])C([H])=C23)C(C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C1([H])[H])=O
InChi Key
AOHSSQNORWQENF-VWLOTQADSA-N
InChi Code
InChI=1S/C31H36N2O6/c1-19(28-26(34)16-31(2,3)17-27(28)35)32-15-9-8-14-25(29(36)37)33-30(38)39-18-24-22-12-6-4-10-20(22)21-11-5-7-13-23(21)24/h4-7,10-13,24-25,34H,8-9,14-18H2,1-3H3,(H,33,38)(H,36,37)/t25-/m0/s1
Chemical Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[1-(2-hydroxy-4,4-dimethyl-6-oxocyclohexen-1-yl)ethylideneamino]hexanoic 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 (~187.75 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.69 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.8775 mL 9.3874 mL 18.7748 mL
5 mM 0.3755 mL 1.8775 mL 3.7550 mL
10 mM 0.1877 mL 0.9387 mL 1.8775 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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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
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g/mol

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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)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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