Cas no 122532-80-3 (Boc-lys(2-picolinoyl)-OH)

Boc-Lys(2-picolinoyl)-OH is a protected lysine derivative featuring a Boc (tert-butoxycarbonyl) group at the N-terminus and a 2-picolinoyl moiety attached to the ε-amino group of lysine. This compound is widely used in peptide synthesis, particularly for introducing modified lysine residues with enhanced stability and specific binding properties. The Boc group provides orthogonal protection, enabling selective deprotection under mild acidic conditions, while the 2-picolinoyl modification imparts metal-chelating capabilities, making it valuable for applications in metalloprotein design or affinity tagging. Its high purity and well-defined structure ensure reproducibility in solid-phase or solution-phase peptide synthesis. The compound is particularly useful in constructing peptide-based probes or bioactive molecules requiring precise functionalization at the lysine side chain.
Boc-lys(2-picolinoyl)-OH structure
Boc-lys(2-picolinoyl)-OH structure
Product Name:Boc-lys(2-picolinoyl)-OH
CAS No:122532-80-3
MF:C17H25N3O5
MW:351.3975045681
CID:137042
Update Time:2025-07-02

Boc-lys(2-picolinoyl)-OH Chemical and Physical Properties

Names and Identifiers

    • L-Lysine,N2-[(1,1-dimethylethoxy)carbonyl]-N6-(2-pyridinylcarbonyl)-
    • Boc-Lys(2-picolinoyl)-OH
    • NA-T-BUTOXYCARBONYL-NE-(2-PICOLINOYL)-L-LYSINE
    • BOC-LYS(2-PICO)-OH
    • BOC-LYSINE(2-PICOLINOYL)-OH
    • N-ALPHA-T-BUTOXYCARBONYL-N-EPSILON-(2-PICOLINOYL)-L-LYSINE
    • Boc-lys(2-picolinoyl)-OH
    • Inchi: 1S/C17H25N3O5/c1-17(2,3)25-16(24)20-13(15(22)23)9-5-7-11-19-14(21)12-8-4-6-10-18-12/h4,6,8,10,13H,5,7,9,11H2,1-3H3,(H,19,21)(H,20,24)(H,22,23)/t13-/m0/s1
    • InChI Key: WDBMDLPFTOIHQM-ZDUSSCGKSA-N
    • SMILES: O(C(N[C@H](C(=O)O)CCCCNC(C1C=CC=CN=1)=O)=O)C(C)(C)C

Computed Properties

  • Exact Mass: 351.17900
  • Monoisotopic Mass: 351.179
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 8
  • Heavy Atom Count: 25
  • Rotatable Bond Count: 12
  • Complexity: 462
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0

Experimental Properties

  • PSA: 117.62000
  • LogP: 2.74140

Boc-lys(2-picolinoyl)-OH Security Information

  • Storage Condition:2-8°C

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Additional information on Boc-lys(2-picolinoyl)-OH

Professional Introduction to Boc-lys(2-picolinoyl)-OH and CAS No 122532-80-3

Boc-lys(2-picolinoyl)-OH is a specialized chemical compound widely utilized in the field of pharmaceutical research and synthesis. This compound, identified by the CAS number CAS NO122532-80-3, plays a crucial role in the development of various bioactive molecules. The name itself provides significant insight into its chemical structure and functionality, highlighting its utility in peptide synthesis and modification.

The compound consists of a protected lysine residue, where the amino group is specifically modified with a Boc (tert-butoxycarbonyl) group, enhancing stability during synthetic processes. Additionally, the side chain of lysine is acylated with a 2-picolinoyl moiety, which imparts unique properties that make it valuable in medicinal chemistry applications. The 2-picolinoyl group, derived from picolinic acid, introduces a nitrogen-containing heterocycle that can influence the electronic and steric environment of the molecule.

In recent years, there has been growing interest in the development of novel peptidomimetics and modified peptides for therapeutic purposes. Boc-lys(2-picolinoyl)-OH has emerged as a key intermediate in these endeavors due to its ability to enhance peptide stability and bioavailability. The Boc protection ensures that the amino group remains unreactive under harsh conditions, allowing for selective modifications at other positions. This property is particularly advantageous in multi-step synthetic routes where orthogonal reactions are required.

One of the most compelling applications of Boc-lys(2-picolinoyl)-OH is in the field of protease inhibition. Proteases are enzymes that play critical roles in various biological pathways, making them attractive targets for drug development. By incorporating this modified lysine residue into peptide sequences, researchers can design inhibitors that exhibit enhanced binding affinity and selectivity. For instance, studies have demonstrated that peptides containing Boc-lys(2-picolinoyl)-OH can effectively inhibit certain proteases by forming stable interactions with their active sites.

The 2-picolinoyl group also contributes to the overall functionality of the compound by influencing its solubility and metabolic stability. Picolinic acid derivatives are known for their ability to interact with biological targets through hydrogen bonding and hydrophobic interactions. This makes Boc-lys(2-picolinoyl)-OH a versatile building block for designing molecules that can modulate biological processes with high precision.

Recent advancements in computational chemistry have further enhanced the utility of Boc-lys(2-picolinoyl)-OH in drug discovery. Molecular modeling studies have revealed that this compound can be integrated into complex molecular frameworks to create novel therapeutic agents. By leveraging computational tools, researchers can predict the binding modes and interactions of Boc-lys(2-picolinoyl)-OH with target proteins, facilitating the design of more effective drugs.

Moreover, the synthesis of Boc-lys(2-picolinoyl)-OH has been optimized to ensure high yield and purity, making it readily available for industrial applications. Modern synthetic methodologies allow for scalable production, enabling pharmaceutical companies to incorporate this compound into their drug development pipelines efficiently. The robustness of its synthetic route also ensures consistency in quality, which is paramount for clinical applications.

The role of Boc-lys(2-picolinoyl)-OH extends beyond protease inhibition; it has also been explored in the development of vaccines and immunomodulators. Peptides modified with this residue have shown promise in eliciting specific immune responses, making them valuable candidates for vaccine design. The ability to fine-tune peptide properties through structural modifications allows for the creation of vaccines with enhanced efficacy and safety profiles.

In conclusion, Boc-lys(2-picolinoyl)-OH (CAS NO122532-80-3) is a multifaceted compound with significant implications in pharmaceutical research and drug development. Its unique chemical structure and functional properties make it an indispensable tool for designing bioactive molecules with therapeutic potential. As research continues to uncover new applications for this compound, its importance in medicinal chemistry is set to grow further.

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