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N-ε-propargyloxycarbonyl-L-lysine (HL-Lys(Poc)-OH)

Cat No.:V67167 Purity: ≥98%
N-ε-propargyloxycarbonyl-L-lysine (HL-Lys(Poc)-OH) is a lysine-based unnatural amino acid (AA) (UAA).
N-ε-propargyloxycarbonyl-L-lysine (HL-Lys(Poc)-OH)
N-ε-propargyloxycarbonyl-L-lysine (HL-Lys(Poc)-OH) Chemical Structure CAS No.: 1215204-46-8
Product category: Fluorescent Dye
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
50mg
100mg
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Other Forms of N-ε-propargyloxycarbonyl-L-lysine (HL-Lys(Poc)-OH):

  • N-ε-propargyloxycarbonyl-L-lysine hydrochloride
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
N-ε-propargyloxycarbonyl-L-lysine (HL-Lys(Poc)-OH) is a lysine-based unnatural amino acid (AA) (UAA). N-ε-propargyloxycarbonyl-L-lysine is extensively used for bioconjugation of fluorescent probes in a variety of organisms. N-ε-propargyloxycarbonyl-L-lysine is a click chemical reagent. It contains Alkyne groups and could undergo CuAAc (copper-catalyzed azide-alkyne cycloaddition reaction) with compounds bearing an Azide group.
N-ε-propargyloxycarbonyl-L-lysine (HL-Lys(Poc)-OH) is a lysine-based unnatural amino acid (UAA) widely used for bio-conjugation of fluorescent probes in diverse organisms. It is a click chemistry reagent containing an alkyne group that can be used for copper-catalyzed azide-alkyne cycloaddition (CuAAC).
Biological Activity I Assay Protocols (From Reference)
Targets
The alkyne group is the primary reactive target. It is designed to react with azide-functionalized molecules (e.g., fluorescent probes, affinity tags) via click chemistry for site-specific labeling.
ln Vitro
The process of molecular hyperspectral SRS imaging involves labeling cellular proteins, including Sec61β, Htt74Q, and the histone H3 variant H3.3, that carry N-ε-propargyloxycarbonyl-L-lysine (HL-Lys(Poc)-OH), with a sensitive Raman tag using click chemistry[1].
There is no specific in vitro activity data for this compound as it is a building block. Its activity is measured by its efficiency in click chemistry reactions. It can be incorporated into proteins via genetic code expansion, enabling site-specific labeling with azide-functionalized probes.
ln Vivo
There is no specific in vivo activity data for this compound. However, when incorporated into proteins in live cells or organisms, it enables in vivo labeling of target proteins via click chemistry, allowing for imaging and tracking studies.
Enzyme Assay
A standard protocol involves dissolving HL-Lys(Poc)-OH in a suitable solvent (e.g., DMSO or PBS) and reacting it with an azide-functionalized fluorescent probe in the presence of a copper catalyst (e.g., CuSO4 and sodium ascorbate) at room temperature for 1-2 hours. The reaction efficiency is assessed by HPLC or mass spectrometry.
Cell Assay
A general protocol for cellular experiments involves expressing a target protein with HL-Lys(Poc)-OH incorporated via amber suppression. After cell lysis or in live cells, an azide-functionalized fluorescent probe is added along with a copper catalyst (or via copper-free click chemistry) to label the protein for imaging or pulldown assays.
Animal Protocol
There is no standard in vivo protocol for this compound. However, in vivo labeling can be performed by injecting an azide-functionalized fluorescent probe into an animal model expressing a Poc-tagged protein. The probe reacts with the Poc group in vivo via click chemistry, enabling imaging of the target protein.
ADME/Pharmacokinetics
General PK properties for this unnatural amino acid are not applicable, as it is a building block. Its stability in biological systems depends on its incorporation into larger molecules and the metabolic stability of the amide bonds. Formulation is typically in DMSO or PBS.
Toxicity/Toxicokinetics
General toxicity for unnatural amino acids is considered low. At working concentrations (uM to mM range), HL-Lys(Poc)-OH exhibits no significant cytotoxicity. Standard safety precautions for handling laboratory chemicals should be observed.
References

[1]. Site-Specific Labeling of Proteins Using Unnatural Amino Acids. Mol Cells. 2019 May 31;42(5):386-396.

[2]. Modified microcystins and nodularins.WO2018206715A2.

Additional Infomation
(2S)-2-amino-6-{[(prop-2-yn-1-yloxy)carbonyl]amino}hexanoic acid is an organic molecular entity.
N-ε-propargyloxycarbonyl-L-lysine is a click chemistry tool for site-specific protein labeling. It contains a propargyl group that can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAC) for conjugation with azide-functionalized probes. This product is for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H16N2O4
Molecular Weight
228.245
Exact Mass
228.111
CAS #
1215204-46-8
Related CAS #
N-ε-propargyloxycarbonyl-L-lysine hydrochloride;1428330-91-9
PubChem CID
49842363
Appearance
White to off-white solid powder
LogP
-2.5
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
8
Heavy Atom Count
16
Complexity
282
Defined Atom Stereocenter Count
1
SMILES
[C@H](N)(CCCCNC(=O)OCC#C)C(=O)O
InChi Key
KRFMMSZGIQEBIJ-QMMMGPOBSA-N
InChi Code
InChI=1S/C10H16N2O4/c1-2-7-16-10(15)12-6-4-3-5-8(11)9(13)14/h1,8H,3-7,11H2,(H,12,15)(H,13,14)/t8-/m0/s1
Chemical Name
(2S)-2-amino-6-(prop-2-ynoxycarbonylamino)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)
H2O: 17.86 mg/mL (78.25 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 16.67 mg/mL (73.03 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.3812 mL 21.9058 mL 43.8116 mL
5 mM 0.8762 mL 4.3812 mL 8.7623 mL
10 mM 0.4381 mL 2.1906 mL 4.3812 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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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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