30189-36-7

Basic information

• Product Name: N,N'-Di-Boc-L-lysine hydroxysuccinimide ester
• Synonyms: N-ALPHA,N-EPSILON-DI-BOC-L-LYSINE HYDROXYSUCCINIMIDE ESTER;N-ALPHA, N-EPSILON-DI-BOC-L-LYSINE N-HYDROXYSUCCINIMIDE ESTER;N-ALPHA,EPSILON-DI-T-BOC-L-LYSINE N-HYDROXYSUCCINIMIDE ESTER;N-ALPHA,EPSILON-BIS-BOC-L-LYSINE N-HYDROXYSUCCINIMIDE ESTER;BOC-LYSINE(BOC)-OSU;BOC-LYS(BOC)-OSU;BOC-L-LYSINE HYDROXYSUCCINIMIDE ESTER;BOC-L-LYSINE A-(TERT-BUTOXYCARBONYL)-L-LYSINE
• CAS NO: 30189-36-7
• Molecular Formula: C₂₀H₃₃N₃O₈
• Molecular Weight: 443.49
• Product Categories: Amino Acids;Lysine [Lys, K];Boc-Amino Acids and Derivative;Boc-Amino acid series
• Mol File: 30189-36-7.mol

Chemical Properties

• Melting Point: 184℃
• Appearance: Off-white/Powder
• Density: 1.21g/cm3
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), DMF (Slightly), DMSO (Slightly)
• PKA: 10.76±0.46(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Moisture Sensitive
• BRN: 1559007
• CAS DataBase Reference: N,N'-Di-Boc-L-lysine hydroxysuccinimide ester(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Di-Boc-L-lysine hydroxysuccinimide ester(30189-36-7)
• EPA Substance Registry System: N,N'-Di-Boc-L-lysine hydroxysuccinimide ester(30189-36-7)

Safety Data

• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 30189-36-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N,N'-Di-Boc-L-lysine hydroxysuccinimide ester is used as a building block for the synthesis of various pharmaceutical compounds. Its application is primarily due to its ability to facilitate the formation of peptide bonds, which are crucial in the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
In the field of chemical synthesis, N,N'-Di-Boc-L-lysine hydroxysuccinimide ester is used as a reagent for the preparation of various organic compounds. Its utility stems from its ability to react with other molecules, allowing for the creation of a wide range of chemical products.
Used in Research and Development:
N,N'-Di-Boc-L-lysine hydroxysuccinimide ester is also utilized in research and development settings, where it serves as a valuable tool for studying the properties and behavior of amino acids and their derivatives. This knowledge can be applied to the design and development of new materials and technologies.
Used as a Local Anesthetic:
N,N'-Di-Boc-L-lysine hydroxysuccinimide ester is used as a local anesthetic in medical applications. Its anesthetic properties are attributed to its ability to block nerve conduction, providing temporary pain relief during surgical procedures or other medical interventions.

Upstream product

• 74124-79-1 di(succinimido) carbonate 
• 2483-46-7 Boc-Lys(Boc)-OH 
• 75513-55-2 N-hydroxysuccinimido diphenyl phosphate 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 56-87-1 L-lysine 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 91129-63-4 Boc-(Lys(Boc))10-4-(hydroxymethyl)benzyl 3β-cholestanyl succinate 
• 76944-95-1 tert-butyl N-[(3S)-2-oxoazepan-3-yl]carbamate 
• 199340-40-4 [(S)-5-(3-{4-[3-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-propylamino]-butylamino}-propylcarbamoyl)-5-tert-butoxycarbonylamino-pentyl]-carbamic acid tert-butyl ester 
• 239115-60-7 C₆₁H₁₀₈N₁₀O₁₃S 
• 239115-69-6 C₆₁H₁₀₆I₂N₁₀O₁₃S 
• 865721-27-3 [5-(5-{4-[6-(2,6-bis-tert-butoxycarbonylamino-hexanoylamino)-2-tert-butoxycarbonylamino-hexanoylamino]-phenylcarbamoyl}-5-tert-butoxycarbonylamino-pentylcarbamoyl)-5-tert-butoxycarbonylamino-pentyl]-carbamic acid tert-butyl ester 
• 199340-42-6 ((S)-5-{3-[(4-{[3-((S)-2-Amino-3-phenyl-propionylamino)-propyl]-tert-butoxycarbonyl-amino}-butyl)-tert-butoxycarbonyl-amino]-propylcarbamoyl}-5-tert-butoxycarbonylamino-pentyl)-carbamic acid tert-butyl ester 
• 199340-44-8 [(S)-5-(3-{[4-({3-[(S)-2-(6-Amino-hexanoylamino)-3-phenyl-propionylamino]-propyl}-tert-butoxycarbonyl-amino)-butyl]-tert-butoxycarbonyl-amino}-propylcarbamoyl)-5-tert-butoxycarbonylamino-pentyl]-carbamic acid tert-butyl ester 
• 199340-41-5 ((S)-5-{3-[(4-{[3-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-propyl]-tert-butoxycarbonyl-amino}-butyl)-tert-butoxycarbonyl-amino]-propylcarbamoyl}-5-tert-butoxycarbonylamino-pentyl)-carbamic acid tert-butyl ester 
• 199340-43-7 [(S)-5-(3-{[4-({3-[(S)-2-(6-Benzyloxycarbonylamino-hexanoylamino)-3-phenyl-propionylamino]-propyl}-tert-butoxycarbonyl-amino)-butyl]-tert-butoxycarbonyl-amino}-propylcarbamoyl)-5-tert-butoxycarbonylamino-pentyl]-carbamic acid tert-butyl ester 
• 1009102-92-4 C₄₀H₅₅ClN₆O₁₁S 
• 1267808-41-2 (S)-2-((S)-2,6-bis-tert-butoxycarbonylaminohexanoylamino)-6-tert-butoxycarbonylaminohexanoic acid benzyl ester 
• 1240503-04-1 C₅₁H₇₈N₆O₄ 

Relevant articles and documents

Heparin versus DNA: Chiral preferences in polyanion binding to self-assembled multivalent (SAMul) nanostructures

This communication presents simple cationic self-assembling multivalent (SAMul) first generation dendrons based on l or d lysine, which form identical nanoscale assemblies in terms of dimensions and charge densities but toward which DNA and heparin exhibit different chiral binding preferences. However, higher generation dendrons with larger hydrophilic head groups are bound identically by these polyanions, irrespective of chirality. We propose that well-organized chiral ligands on the surface of self-assembled nanostructures can exhibit enantioselective polyanion binding. This demonstrates that small structural changes can be amplified by self-assembly and impact on nanoscale binding.

PH-sensitive cationic lipopeptides for the design of drug-delivery systems

Lipopeptides on the basis of L-glutamic acid and glutamine di-and monoesters with aliphatic alcohols of various lengths that contain L-arginine, L-ornithine, and L-lysine were synthesized. The behavior of these amphiphiles in aqueous medium was shown to depend on their structure. Pleiades Publishing, Inc., 2006.

A Collaborative Assembly Strategy for Tumor-Targeted siRNA Delivery

A novel "collaborative assembly" approach was reported for the synthesis of an siRNA delivery system via a combination of an electrostatically driven physical assembly and a facile click reaction-mediated chemical assembly, which showed various advantages

Ynamide-Mediated Thiopeptide Synthesis

Exploration of the full potential of thioamide substitution as a tool in the chemical biology of peptides and proteins has been hampered by insufficient synthetic strategies for the site-specific introduction of a thioamide bond into a peptide backbone. A novel ynamide-mediated two-step strategy for thiopeptide bond formation with readily available monothiocarboxylic acids as thioacyl donors is described. The α-thioacyloxyenamide intermediates formed from the ynamides and monothiocarboxylic acids can be purified, characterized, and stored. The balance between their activity and stability enables them to act as effective thioacylating reagents to afford thiopeptide bonds under mild reaction conditions. Amino acid functional groups such as OH, CONH2, and indole NH groups need not be protected during thiopeptide synthesis. The modular nature of this strategy enables the site-specific incorporation of a thioamide bond into peptide backbones in both solution and the solid phase.

Self-assembling tryptophan-based designer peptides as intracellular delivery vehicles

A series of tryptophan-based peptides W1a, b-W4a, b, with diverse architectures were designed and synthesized. These tryptophan containing peptides can self-assemble to spherical particle. This self-assembled system was demonstrated to encapsulate rhodamine B and penetrate the cell membrane.

One-pot orthogonal copper-catalyzed synthesis and self-assembly of l-lysine-decorated polymeric dendrimers

Synthetic peptides, including cyclic peptides and peptidomimetics, provide stability, protection, and long circulation times compared to free-circulating peptides. Dendritic structures with amino acids or peptides attached to the peripheral layer represent one form of peptidomimetics (i.e., a hybrid peptide/dendrimer construct) that has found use in biological applications. Constructing such dendritic structures from linear polymeric building blocks provides a further advantage of generating a highly ordered and defined structure in the nanoparticle size range. However, the rapid synthesis of such well-defined structures is still a challenge. In this work, we demonstrate that through modulating the copper activity concomitantly of the nitroxide radical coupling (NRC) and the azide-alkyne cycloaddition (CuAAC) reactions, polymeric dendrimers decorated with l-lysine on the periphery could be made rapidly in one pot at 25 °C. Three polymeric dendrimers were constructed with high purity (>94%) and with varying l-lysine density coated on the peripheral generation layer. The self-assembly of these dendrimers in water gave similar sizes to that found in organic solvents, suggesting that the aggregation number of dendritic structures in water was very low and possibly consisting of unimolecular micelles. The findings support the conclusion that the self-assembly of a dendritic architecture in water produces nanoparticles with predictable and well-controlled sizes. This synthetic methodology and the self-assembly properties represent an important step toward synthesizing peptide-decorated dendrimers targeted toward therapeutic applications.

GSH- and pH-responsive drug delivery system constructed by water-soluble pillar[5]arene and lysine derivative for controllable drug release

Novel GSH- and pH-responsive supramolecular vesicles constructed by an amphiphilic inclusion complex formed from water-soluble pillar[5]arene and lysine derivative have been successfully developed, which can efficiently encapsulate anticancer drug MTZ and show rapid MTZ-release in a simulated acidic tumor environment with high GSH concentration, and exhibit potent antitumor activity.

Fluorescent dyes

Chemically reactive carbocyanine dyes that are intramolecularly crosslinked between the 1-position and 3′-position, their bioconjugates and their uses are described. 1,3′-crosslinked carbocyanines are superior to those of conjugates of spectrally similar 1,1′-crosslinked or non-crosslinked dyes. The invention includes derivative compounds having one or more benzo nitrogens.

Facile and universal immobilization of l-lysine inspired by mussels

A novel functional molecule lysine-dopamine (LDA) was successfully synthesized and explored as a universal modifier for different types of surfaces, inspired by mussel adhesive moiety dopamine and bio-functional moiety l-lysine. The universal, robust, and efficient surface modification based on LDA was achieved through a facile and cost-effective dip-coating process, confirmed by Fourier transform infrared spectroscopy (FTIR), contact angle, X-ray photoelectron spectroscopy (XPS) and scanning electron microscope-energy dispersive spectroscopy (SEM-EDS) measurements. Meanwhile, LDA modification improved cell adhesion, promoted cell growth, and accelerated endothelialization on the substrate surface and provided plasma clot lysis activity. The results indicated that the surface biocompatibility was obviously improved by the one-step modification method for the immobilized l-lysine.

Prodrugs comprising an exendin linker conjugate

The present invention relates to a prodrug or a pharmaceutically acceptable salt thereof comprising an exendin linker conjugate D-L, wherein D represents an exendin moiety; and -L is a non-biologically active linker moiety -L1 represented by formula (I), wherein the dashed line indicates the attachment to one of the amino groups of the exendin moiety by forming an amide bond. The invention further relates to pharmaceutical compositions comprising said prodrugs as well as their use as a medicament for treating or preventing diseases or disorders which can be treated by exendin.