2389-60-8

Basic information

• Product Name: Z-LYS(BOC)-OH
• Synonyms: CBZ-L-LYSINE(BOC);Butoxycarbonylcarbobenzoxylysine;n^(epsilum)-(tert-Butoxycarbonyl)-N^(alpha)-carbobenzoxy-L-lysine;IN2-(benzyloxycarbonyl)-N6-(tert-butoxycarbonyl)-L-lysine;Cbz-Lys(Boc)-OH;N-α-Z-N-ε-Boc-L-lysine;NALPHA-Benzyloxycarbonyl-NEPSILON-tert-butoxycarbonyl-L-lysine;N2-Z-N6-BOC-LYSINE
• CAS NO: 2389-60-8
• Molecular Formula: C₁₉H₂₈N₂O₆
• Molecular Weight: 380.44
• EINECS: 219-223-1
• Product Categories: Amino Acids;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Cbz-Amino Acids;Z-Amino acid series
• Mol File: 2389-60-8.mol

Chemical Properties

• Melting Point: 63-70°C
• Boiling Point: 587 °C at 760 mmHg
• Flash Point: 308.8 °C
• Appearance: White crystals
• Density: 1.176 g/cm³
• Vapor Pressure: 1.26E-14mmHg at 25°C
• Refractive Index: -6 ° (C=1, MeOH)
• Storage Temp.: 2-8°C
• Solubility: Soluble in DMF (0.5 mmol/ml).
• PKA: 3.98±0.21(Predicted)
• CAS DataBase Reference: Z-LYS(BOC)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-LYS(BOC)-OH(2389-60-8)
• EPA Substance Registry System: Z-LYS(BOC)-OH(2389-60-8)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 2389-60-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Z-LYS(BOC)-OH is used as a key intermediate for the synthesis of various organic compounds, providing a versatile building block for the development of new molecules with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, Z-LYS(BOC)-OH is utilized as a crucial component in the synthesis of peptide-based drugs and other bioactive molecules. Its presence in the synthesis process aids in the development of innovative therapeutic agents.
Used in Agrochemicals:
Z-LYS(BOC)-OH plays a significant role in the agrochemical industry, where it is employed as a precursor for the synthesis of various agrochemical products, such as pesticides and herbicides, contributing to the development of more effective and environmentally friendly solutions for agriculture.
Used in Dyestuff Industry:
In the dyestuff industry, Z-LYS(BOC)-OH is used as a vital intermediate for the production of dyes and pigments. Its unique chemical properties enable the creation of a wide range of colorants for various applications, including textiles, plastics, and printing inks.

InChI:InChI=1/C19H28N2O6/c1-19(2,3)27-17(24)20-12-8-7-11-15(16(22)23)21-18(25)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

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 2212-75-1 N₂-[(benzyloxy)carbonyl]-L-lysine 
• 18595-34-1 tert-butyl fluoroformate 
• 16965-08-5 1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate 
• 2418-95-3 (S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid 
• 501-53-1 benzyl chloroformate 
• 6627-89-0 tert-butyl phenyl carbonate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 130384-98-4 tert-butyl 1H-benzo[d][1,2,3]triazole-1-carboxylate 
• 657-27-2 L-Lysine hydrochloride 
• 14511-39-8 2(S)-2-amino-6-(benzylideneamino)hexanoic acid 
• 2212-76-2 N^α-benzyloxycarbonyl-N^ε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt 
• 56-87-1 L-lysine 

Downstream Products

• 50903-60-1 Z-L-Lys(BOC)-OPFP 
• 40290-73-1 Z-Lys(Boc)-Lys(Boc)-OtBu 
• 38155-01-0 Z-Lys(Boc)-Glu(OtBu)-OMe 
• 10342-52-6 N^α-Benzyloxycarbonyl-N^ε-tert-butyloxycarbonyl-L-lysylglycine Methyl Ester 
• 23556-66-3 N-alpha-carbobenzoxy-N-epsilon-t-butyloxycarbonyl-L-lysyl-N-epsilon-t-butyloxycarbonyl-L-lysine methyl ester 
• 24828-95-3 N-benzyloxycarbonyl-N^ε-tert-butyloxycarbonyl-lysine amide 
• 7750-44-9 Z-Lys(εBoc)-OtBu 
• 2389-49-3 N^α-(benzyloxycarbonyl)-N^ε-(tert-butoxycarbonyl)-L-lysine methyl ester 
• 95930-15-7 3-(N^α-benzyloxycarbonyl-N^ε-t-butoxycarbonyl-lysyl)-1,3-thiazolidine-2-thione 
• 2212-69-3 N₂-benzyloxycarbonyl-N₆-t-butoxycarbonyl-L-lysine 4-nitrophenyl ester 
• 21869-27-2 N-(N^α-carbobenzoxy-N^ε-tert-butoxycarbonyl-L-lysyl)glycine ethyl ester 
• 128684-45-7 Z-Lys(Boc)-D-Trp-isoamylamide 
• 97640-04-5 N^α-benzyloxycarbonyl-N^ε-tert-butyloxycarbonyllysyl-N^ε-tert-butyloxycarbonyllysyl-leucine tert-butyl ester 
• 137271-91-1 ethyl N_α-benzyloxycarbonyl-N_ε-(t-butyloxycarbonyl)-L-lysyl-4(S)-amino-2(E)-penten-oate 

Relevant articles and documents

Structure-delivery relationships of lysine-based gemini surfactants and their lipoplexes

The synthesis and properties of gemini surfactants of the type (R 1(CO)-Lys(H)-NH)2(CH2)n are reported. For a spacer length of n = 6, the hydrophobic acyl tail was varied in length (R1 = C8, C10, C12, C14, C16, and C18) and, for R1 = C18, the degree of unsaturation. For R1(CO) = oleoyl (C18:1 Z) the spacer length (n = 2-8) and the stereochemistry of the lysine building block were varied; a 'half-gemini' derivative with a single oleoyl tail and head group was also prepared. The potential of the gemini surfactants to transfer polynucleotides across a cell membrane was investigated by transfection of HeLa cells with beta-galactosidase, both in the presence and absence of the helper lipid DOPE. Oleoyl was found to be by far the best hydrophobic tail for this biological activity, whereas the effect of the lysine stereochemistry was less pronounced. The effect of an optimum spacer length (n = 6) was observed only in the absence of helper lipid. The most active surfactant, i.e. the one with oleoyl chains and n = 6, formed liposomes with sizes in the range of 60-350 nm, and its lipoplex underwent a transition from a lamellar to a hexagonal morphology upon lowering the pH from 7 to 3. the Partner Organisations 2014.

Syntheses of Enantiopure 1,2-Ethylenediamines with Tethered Secondary Amines of the Formula H 2NCH 2CH[(CH 2) nNHMe]NH 2(n = 1-4) from α-Amino Acids: New Agents for Asymmetric Catalysis

Tris(hydrochloride) adducts of the title compounds-are prepared from the inexpensive α-amino acids H 2 N(C=O)CH 2 CH(NH 2)CO 2 H, HO(C=O)(CH 2) n ′ CH(NH 2)CO 2 H (n ′ = 1, 2), and H2 N(CH 2) 4 CH(NH 2)CO 2 H, respectively (steps/overall yield = 5/32, 7/30, 7/33, 5/38). The NH 2 group that is remote from the secondary amine is installed via BH 3 reduction of an amide [-(C=O)NR 2[ derived?-from an α-amino carboxylic acid. The MeNHCH 2 units are introduced by BH 3 reductions of alkyl carbamate [RO(C=O)NHCH 2-; R = Et, t-Bu] or amide [MeHN(C=O)-] moieties.

CHIRAL CYCLEN COMPOUNDS AND THEIR USES

The present invention relates to the preparation of a series of chiral DOTA, D03A, D02A, DO1A, cyclen and their metal complexes, which display properties superior to those of previous DOTA- based compounds, and hence are potentially valuable as a platform for diagnostic applications. The chiral DOTAs reveal a high abundance of twisted square antiprism (TSA) geometry favoring them to be used as potential MRI contrast agents, whereas their rapid labelling properties at mild conditions make them excellent candidates for use as radiometal chelators.

Serine- and threonine-derived diamine equivalents for site-specific incorporation of platinum centers in peptides, and the anticancer potential of these conjugates

A modular strategy that allows introduction of one or more reactive platinum units at chosen locations along a peptide sequence is presented. This makes use of diazides generated from serine and threonine as diamine equivalents which can be conjugated to the peptide under standard coupling conditions. Reduction of these diazides using Pd/C and H2 followed by platination affords the final products in good yields. Following this, we prepared a new class of peptide-platinum conjugates and carried out preliminary cytotoxicity evaluation and DNA interaction studies. Inclusion of lysine residues in the sequence was found to improve DNA interaction and anticancer activities compared to analogous conjugates with hydrophobic side chains.

Macrocyclic hexaoxazoles: Influence of aminoalkyl substituents on RNA and DNA G-quadruplex stabilization and cytotoxicity

A series of 24-membered macrocyclic hexaoxazoles containing one or two aminoalkyl substituents was synthesized and evaluated for cytotoxicity and for their ability to selectively stabilize G-quadruplex DNA and RNA. The most cytotoxic analog 4a, with IC50 values of 25 and 130 nM using KB3-1 and RPMI 8402 cells, is efficacious in vivo in athymic nude mice with a human tumor xenograft from the breast cancer cell line MDA-MB-435.

THERAPEUTIC COMPOUNDS

The invention provides compounds of formula I: wherein A, B, D, E, R1, R2, R3, R4, R5, X, and ----- have any values defined herein, as well as salts thereof. The compounds have activity as G-quadruplex DNA stabilizers and as anti-proliferative agents.

THERAPEUTIC COMPOUNDS

The invention provides compounds of formula (I) wherein A, B, R1, F, G, n, n' and the dotted line have any values defined herein, as well as salts thereof. The compounds have activity as anti-proliferative agents.

PROCESS FOR THE PREPARATION OF ε-ALKOXYCARBONYLLYSINES AND THEIR ANALOGUES

A process for the preparation of ω-alkoxycarbonylamino-α-aminoacids and α,ω orthogonally diprotected diaminoacids from α,ω-diaminoacids using 1- alkoxycarbonylbenzotriazoles as protecting agents is disclosed. In an alternative embodiment, carbamoylating agents in the presence of benzotriazoles are used instead of 1-alkoxycarbonylbenzotriazoles. This reaction is preferably applied to the preparation of ε- alkoxycarbonyllysines from lysine. A process for the preparation of t-butoxycarbonylbenzotriazoles and novel complexes of ω-alkoxycarbonylamino-α-aminoacids with benzotriazoles are also disclosed.

THERAPEUTIC COMPOUNDS

The invention provides compounds of formula I: wherein A, B, D, E, R1, R2, R3, R4, R5, X, and ----- have any values defined herein, as well as salts thereof. The compounds have activity as G-quadruplex DNA stabalizers and as anti-proliferative agents.

Synthesis and evaluation of peptidic maleimides as transglutaminase inhibitors

A series of novel transglutaminase inhibitors was prepared, based on the scaffold of a commonly used peptide substrate and bearing an electrophilic maleimide group. These compounds were evaluated in vitro and shown to lead to irreversible inactivation of tissue transglutaminase. Comparison with inhibitors studied previously provides insight into the steric environment of the enzyme active site.