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• 2. Enabling shape memory and healable effects in a conjugated polymer by incorporating siloxane via dynamic imine bond?
  Yaling Zhang,Chunhui Dai,Shiwei Zhou,Bin Liu Chem. Commun., 2018,54, 10092-10095
• 3. Fate of Sb(v) and Sb(iii) species along a gradient of pH and oxygen concentration in the Carnoulès mine waters (Southern France)
  Eléonore Resongles,Corinne Casiot,Fran?oise Elbaz-Poulichet,Rémi Freydier,Odile Bruneel,Christine Piot,Sophie Delpoux,Aurélie Volant,Angélique Desoeuvre Environ. Sci.: Processes Impacts, 2013,15, 1536-1544
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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Amino acids and derivatives

Na,Nε-Bis-boc-L-lysine tert-Butyl Ester: A Versatile Building Block in Peptide Chemistry and Drug Development

Na,Nε-Bis-boc-L-lysine tert-butyl ester, with CAS registry number 97347-28-9, is a critical synthetic intermediate in the field of peptide chemistry and medicinal chemistry. This compound, characterized by its dual Boc (tert-butyloxycarbonyl) protecting groups on the α-amino and ε-amino functionalities of L-lysine, serves as a foundational material for constructing complex polypeptide architectures. Recent advancements in solid-phase peptide synthesis (SPPS) have highlighted its role in enabling site-specific functionalization, particularly in the design of bioconjugates and targeted drug delivery systems.

The unique structural features of this compound—specifically the dual Boc protection scheme—allow precise control over deprotection steps during synthesis. A 2023 study published in Journal of Medicinal Chemistry demonstrated its utility in synthesizing multi-branched peptides for cancer immunotherapy applications. Researchers utilized the ε-amino group as a conjugation site for tumor-targeting ligands while maintaining the α-amino group protected during early synthesis phases, showcasing its adaptability in modular assembly strategies.

In the context of protein engineering, this compound has emerged as a key component in generating site-specific antibody-drug conjugates (ADCs). A groundbreaking 2024 paper from the Nature Biotechnology highlighted its integration into lysine-selective click chemistry platforms, enabling efficient conjugation of cytotoxic payloads to antibodies without interfering with native protein structures. The tert-butyl ester functionality further facilitates orthogonal deprotection protocols when combined with other protecting groups like Fmoc or Alloc.

Beyond therapeutic applications, this compound plays an essential role in analytical chemistry through its use as a calibrant in mass spectrometry-based proteomics workflows. Recent methodological improvements reported in Analytical Chemistry (2023) demonstrated how derivatized forms of this compound enhance detection sensitivity for post-translational modifications such as phosphorylation and glycosylation sites.

The synthesis pathway of this compound has undergone significant optimization over the past decade. Modern protocols now employ environmentally benign conditions involving microwave-assisted organic synthesis (MAOS), reducing reaction times from 18 hours to under 60 minutes while maintaining >95% purity according to GC/MS analysis standards established by IUPAC guidelines.

In preclinical drug development pipelines, this reagent is increasingly used to create prodrug constructs that improve pharmacokinetic profiles. A notable example involves coupling it with hydrophobic drug moieties via hydrazone linkers, allowing controlled release mechanisms triggered by physiological pH changes or enzymatic activity—a strategy validated through pharmacokinetic studies published in Bioconjugate Chemistry early 2024.

Safety considerations remain paramount when handling this compound despite its non-toxic classification under current regulatory frameworks. Best practices emphasize maintaining nitrogen-purged storage conditions due to its susceptibility to hydrolysis under humid environments, as documented by stability testing protocols from ISO/IEC 17025-accredited labs.

Ongoing research focuses on expanding its application into next-generation therapies such as mRNA lipid nanoparticle formulations and cell-penetrating peptide vectors. Preliminary data from ongoing studies at MIT's Koch Institute suggest potential roles in enhancing endosomal escape efficiency through strategic placement within carrier architectures—a breakthrough that could revolutionize gene therapy delivery mechanisms.

• 2419-94-5(N-Boc-L-glutamic acid)
• 53308-95-5(Boc-Nva-OH)
• 34582-32-6((S)-4-(tert-Butoxy)-3-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid)
• 16937-99-8((tert-Butoxycarbonyl)-D-leucine)
• 13139-15-6(Boc-L-Leu-OH)
• 13726-84-6(Boc-Glu(OtBu)-OH)
• 24277-39-2(Boc-Glu-OtBu)
• 21887-64-9(Nα-Boc-L-Ornithine)
• 13734-28-6(Boc-Lys-OH)
• 1676-90-0(Boc-Asp(OtBu)-OH)