2389-45-9

Basic information

• Product Name: N-Boc-N'-Cbz-L-lysine
• Synonyms: NALPHA-BOC-NEPSILON-CBZ-L-LYSINE;NALPHA-BOC-NEPSILON-Z-L-LYSINE;N-ALPHA-T-BUTYLOXYCARBONYL-N-EPSILON-BENZYLOXYCARBONYL-L-LYSINE;NALPHA-(TERT-BUTOXYCARBONYL)-NEPSILON-CARBOBENZOXY-L-LYSINE;NALPHA-TERT-BUTOXYCARBONYL-NOMEGA-BENZYLOXYCARBONYL-L-LYSINE;N ALPHA-T-BUTOXYCARBONYL-N OMEGA-BENZYLOXYCARBONYL-L-LYSINE;N-ALPHA-T-BUTOXYCARBONYL-N-EPSILON-CARBOBENZOXY-L-LYSINE;N-ALPHA-TERT-BUTYLOXYCARBONYL-N-EPSILON-BENZYLOXYCARBONYL-L-LYSINE
• CAS NO: 2389-45-9
• Molecular Formula: C₁₉H₂₈N₂O₆
• Molecular Weight: 380.44
• EINECS: 219-221-0
• Product Categories: Amino Acid Derivatives;Amino Acids;Lysine [Lys, K];Boc-Amino Acids and Derivative;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Cbz-Amino Acids;Boc-Amino acid series
• Mol File: 2389-45-9.mol
• Article Data: 19

Chemical Properties

• Melting Point: 75.0 to 79.0 °C
• Boiling Point: 587 °C at 760 mmHg
• Flash Point: 308.8 °C
• Appearance: /
• Density: 1.176 g/cm³
• Vapor Pressure: 1.26E-14mmHg at 25°C
• Refractive Index: -8 ° (C=2.5, AcOH)
• Storage Temp.: −20°C
• Solubility: almost transparency in Acetic acid
• PKA: 3.99±0.21(Predicted)
• BRN: 1917222
• CAS DataBase Reference: N-Boc-N'-Cbz-L-lysine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-N'-Cbz-L-lysine(2389-45-9)
• EPA Substance Registry System: N-Boc-N'-Cbz-L-lysine(2389-45-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 2389-45-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Boc-N'-Cbz-L-lysine is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its protected structure allows for controlled peptide synthesis, enabling the development of new drugs and therapeutic agents.
Used in Research and Development:
In the field of research and development, N-Boc-N'-Cbz-L-lysine serves as a valuable tool for studying peptide synthesis and related biochemical processes. It can be used to investigate the mechanisms of protein folding, enzyme activity, and other biological functions.
Used in Cosmetics Industry:
N-Boc-N'-Cbz-L-lysine can be used in the cosmetics industry as a component of peptide-based cosmetic products. Its ability to form stable peptides can contribute to the development of anti-aging, skin repair, and other cosmetic formulations.
Used in Synthesis of Isodesmosine Chloride:
N-Boc-N'-Cbz-L-lysine is used in the synthesis of Isodesmosine Chloride (I815050), which is a component of elastin. N-Boc-N'-Cbz-L-lysine has potential applications in the development of treatments for connective tissue disorders and other medical conditions related to elastin dysfunction.

InChI:InChI=1/C19H28N2O6/c1-19(2,3)27-18(25)21-15(16(22)23)11-7-8-12-20-17(24)26-13-14-9-5-4-6-10-14/h4-6,9-10,15H,7-8,11-13H2,1-3H3,(H,20,24)(H,21,25)(H,22,23)/t15-/m1/s1

Upstream product

• 16965-08-5 1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate 
• 1155-64-2 N₆-[(benzyloxy)carbonyl]-L-lysine 
• 73548-77-3 Boc-L-Lys(Z)-OMe 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 24424-99-5 di-tert-butyl dicarbonate 
• 32302-83-3 N-ε-benzyloxycarbonyl lysine 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 13734-28-6 Boc-Lys-OH 
• 501-53-1 benzyl chloroformate 
• 657-27-2 L-Lysine hydrochloride 
• 39608-52-1 benzyl carbonochloridate 
• 56-87-1 L-lysine 
• 51814-48-3 t-Boc-L-Lys(Z)-OPAO 
• 77236-13-6 N-α-tert-Butyloxycarbonyl-N-ε-carbobenzoxy-L-lysine benzyl ester 

Downstream Products

• 138848-81-4 [(S)-5-tert-Butoxycarbonylamino-6-(3,4-dihydro-2H-quinolin-1-yl)-6-oxo-hexyl]-carbamic acid benzyl ester 
• 1026632-09-6 ((S)-5-tert-Butoxycarbonylamino-5-{(S)-1-[(S)-2-cyclohexyl-1-((2S,4R)-4-methyl-5-oxo-tetrahydro-furan-2-yl)-ethylcarbamoyl]-2-methyl-propylcarbamoyl}-pentyl)-carbamic acid benzyl ester 
• 1025914-41-3 ((S)-5-tert-Butoxycarbonylamino-5-{(1S,2S)-1-[(S)-2-cyclohexyl-1-((2S,4R)-4-methyl-5-oxo-tetrahydro-furan-2-yl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-pentyl)-carbamic acid benzyl ester 
• 56-87-1 L-lysine 
• 55592-81-9 N^ε-(benzyloxycarbonyl)-N^α-(tert-butoxycarbonyl)-L-lysinamide 
• 1155-64-2 N₆-[(benzyloxy)carbonyl]-L-lysine 
• 133010-10-3 BOC-Lys(Z)-F 
• 145730-89-8 N²-(1,1-dimethylethoxycarbonyl)-N⁶-(phenylmethoxycarbonyl)-L-lysine-2-phenethylamide 
• 73548-77-3 Boc-L-Lys(Z)-OMe 
• 51078-31-0 N^α-Boc-N^ε-Z-lysine p-nitroanilide 
• 33043-26-4 N-(N^α-tert-butoxycarbonyl-N^ε-carbobenzoxy-L-lysyl)glycine ethyl ester 
• 183947-71-9 4-{4-[((S)-6-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoylamino)-methyl]-benzyl}-benzoic acid methyl ester 
• 61131-25-7 Boc-Lys(Z)-Asp(OBzl)-OH 
• 33043-27-5 BOC-Lys(Z)-Gly-NH₂ 

Relevant articles and documents

Enantioselective Deaminative Alkylation of Amino Acid Derivatives with Unactivated Olefins

Herein, we report the first Ni-catalyzed enantioselective deaminative alkylation of amino acid and peptide derivatives with unactivated olefins. Key for success was the discovery of a new sterically encumbered bis(oxazoline) ligand backbone, thus offering a de novo technology for accessing enantioenriched sp3-sp3 linkages via sp3 C-N functionalization. Our protocol is distinguished by its broad scope and generality across a wide number of counterparts, even in the context of late-stage functionalization. In addition, an enantioselective deaminative remote hydroalkylation reaction of unactivated internal olefins is within reach, thus providing a useful entry point for forging enantioenriched sp3-sp3 centers at remote sp3 C-H sites.

Pillar[5]arene-Based Polycationic Glyco[2]rotaxanes Designed as Pseudomonas aeruginosa Antibiofilm Agents

Pseudomonas aeruginosa (P.A.) is a human pathogen belonging to the top priorities for the discovery of new therapeutic solutions. Its propensity to generate biofilms strongly complicates the treatments required to cure P.A. infections. Herein, we describe the synthesis of a series of novel rotaxanes composed of a central galactosylated pillar[5]arene, a tetrafucosylated dendron, and a tetraguanidinium subunit. Besides the high affinity of the final glycorotaxanes for the two P.A. lectins LecA and LecB, potent inhibition levels of biofilm growth were evidenced, showing that their three subunits work synergistically. An antibiofilm assay using a double δlecAδlecB mutant compared to the wild type demonstrated that the antibiofilm activity of the best glycorotaxane is lectin-mediated. Such antibiofilm potency had rarely been reached in the literature. Importantly, none of the final rotaxanes was bactericidal, showing that their antibiofilm activity does not depend on bacteria killing, which is a rare feature for antibiofilm agents.

METHODS OF PREPARING N6-((2-AZIDOETHOXY)CARBONYL)LYSINE

Disclosed herein are methods of preparing N6-((2-azidoethoxy)carbonyl)lysine, N6-((2-azidoethoxy)carbonyl)-L-lysine, and N6-((2-azidoethoxy)carbonyl)-D-lysine. Also disclosed herein are the compounds tert-butyl N2-(tert-butoxycarbonyl)-N6-((2-chloroethoxy)carbonyl)-L-lysinate and tertbutyl N6-((2-azidoethoxy)carbonyl)-N2-(tert-butoxycarbonyl)-L-lysinate, and uses thereof.

IMMUNOSTIMULATING AGENT

The present invention aims to provide an immunostimulating agent superior in an immunostimulatory effect, particularly a compound useful as a vaccine adjuvant, a pharmaceutical composition containing the compound, a vaccine containing the compound and an antigen. An immunostimulating agent containing at least one kind of a compound represented by the formula (I): wherein each symbol is as defined in the present specification, or a salt thereof.

INHIBITORS OF LYSINE GINGIPAIN

The present invention relates generally to therapeutics targeting the bacterium Porphyromonas gingivalis, including its protease Lysine gingipain (Kgp), and their use for the treatment of disorders associated with P. gingivalis infection, including brain disorders such as Alzheimer's disease. In certain embodiments, the invention provides compounds according to Formula I, as described herein, and pharmaceutically acceptable salts thereof.

Unusual orthogonality in the cleavage process of closely related chelating protecting groups for carboxylic acids by using different metal ions

Three structurally related relay protecting groups for carboxylic acids that are based on chelating amines have been developed. These protecting groups can easily be introduced by coupling the carboxylic acid and the corresponding amine in the presence of 2-(1Hbenzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU). In addition to being stable to a whole array of reaction conditions, these protecting groups are also stable under acidic and basic conditions, allowing them to be used in combination with the ester protection of carboxylic acids. The cleavage of these protecting groups is activated by the chelation of metal ions, involving an unusual coordination of the amide nitrogen. Despite their similarity, cleavage of these protecting groups is possible in both a stepwise and an orthogonal fashion by applying different metal salts.

Design, synthesis and preliminary activity evaluation of novel L-lysine derivatives as aminopeptidase N/CD13 inhibitors

A novel class of L-lysine derivatives as aminopeptidase N (APN) inhibitors was designed and synthesized. Activity evaluation showed that compound C7 (IC50 = 9.6 ± 1.3 μM) and C20 (IC50 = 13.6 ± 1.9 μM) were equivalent to the positive control Bestatin (IC50 = 11.3 ± 1.6 μM).

HETEROCYCLIC SCAFFOLDS USEFUL FOR PREPARATION OF COMBINATORIAL LIBRARIES, LIBRARIES AND METHODS OF PREPARATION THEREOF

Disclosed are heterocyclic scaffolds useful, for example, for solid-phase organic synthesis of combinatorial libraries and methods for the preparation thereof. Also disclosed are libraries, including combinatorial libraries, and methods for preparation thereof. Exemplified are the following scaffolds (I):

ACE-INHIBITORS HAVING ANTIOXIDANT AND NO-DONOR ACTIVITY

Multifonctional ACE inhibitor compounds are provided, that combine ACE-inhibiting activity with capability to scavenge superoxide and other reactive oxygen species, and that may further function as nitric oxide donors. The compounds are useful for preventing or treating various disorders, including cardiovascular, and diabetes associated disorders.

Selective nitrolytic deprotection of N-BOC-amines and N-BOC-amino acids derivatives

The extension of the deprotection procedure using HNO3 in CH2Cl2 to a number of appropriately selected N-BOC-masked amines and derivatives of natural amino acids was investigated. The method was found to work effectively with almost all tested substrates, with the exception of activated aromatic amines and heterocycles which underwent unavoidable faster oxidation. Alanine, phenylalanine, serine and lysine derivatives were efficiently deprotected, as well as dipeptide Ala-Phe, preserving the configuration of the substrates and without affecting copresent Z and ester functions, with a remarkable selectivity towards acid sensitive t-butyl esters. The obtained amino acids esters, isolated and characterized in the form of nitrates salts, proved to be suitable intermediates to be used in peptide synthesis.