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

Description

N-Boc-N'-Cbz-L-lysine, also known as Boc-Lys(Z)-OH, is a chemical compound derived from L-lysine, an essential amino acid. It is modified with a Boc (tert-butyloxycarbonyl) group at the N-terminus and a Cbz (benzyloxycarbonyl) group at the N'-terminus, which protect the amino and carboxyl groups, respectively. N-Boc-N'-Cbz-L-lysine is a building block for peptide synthesis and has potential applications in various industries.

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

• 73548-77-3 Boc-L-Lys(Z)-OMe 
• 77236-13-6 N-α-tert-Butyloxycarbonyl-N-ε-carbobenzoxy-L-lysine benzyl ester 
• 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 
• 1155-64-2 N₆-[(benzyloxy)carbonyl]-L-lysine 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 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 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 

Downstream Products

• 16948-05-3 Boc-Lys(Z)-OTcp 
• 73548-77-3 Boc-L-Lys(Z)-OMe 
• 82869-11-2 Boc-L-Lys(Z)-CH₂Cl 
• 138848-81-4 [(S)-5-tert-Butoxycarbonylamino-6-(3,4-dihydro-2H-quinolin-1-yl)-6-oxo-hexyl]-carbamic acid benzyl ester 
• 89121-14-2 (S)-6-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoic acid 2-trimethylsilanyl-ethyl ester 
• 83361-27-7 {(S)-5-tert-Butoxycarbonylamino-5-[(S)-1-(5-methyl-2-phenyl-2H-pyrazol-3-ylcarbamoyl)-2-phenyl-ethylcarbamoyl]-pentyl}-carbamic acid benzyl ester 
• 83361-29-9 N^α-Boc-N^ε-Z-lisil-fenilalanil-fenilalanil-N-(1-fenil-3-metil)-5-pirazolilammide 
• 68168-48-9 Boc-Lys(Z)-Lys(Z)-Gly-OEt 
• 65001-81-2 N^α-Boc-N^ε-Z-Lys-o-nitrophenylester 
• 24458-14-8 Lys(Z)-OBzl 
• 66449-93-2 Boc-Lys(Z)-ONB 
• 192805-65-5 [(S)-5-tert-Butoxycarbonylamino-5-(2-cyclohexyl-ethylcarbamoyl)-pentyl]-carbamic acid benzyl ester 
• 205524-60-3 (S)-2-[2-((S)-6-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoylamino)-acetylamino]-4-bromo-butyric acid methyl ester 
• 387866-56-0 8-benzyloxycarbonylamino-4(S)-tert-butoxycarbonylamino-3-oxooctanoic acid allyl ester 

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.

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.

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.