2389-49-3

Usage

Uses

Used in Pharmaceutical Industry:
Z-Lys(Boc)-OMe is used as a building block in the synthesis of peptide-based drugs and drug delivery systems. Its unique structure allows for the development of stimuli-responsive cationic nanoparticles, which can be triggered to release their cargo in response to specific stimuli, such as pH changes or enzymatic activity. This property makes it a promising candidate for targeted drug delivery and controlled release applications.
Used in Chemical Synthesis:
Z-Lys(Boc)-OMe is used as an intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals. Its versatility as a building block allows for the creation of a wide range of products with diverse applications.
Used in Research and Development:
Z-Lys(Boc)-OMe is utilized in research settings to study the properties and behavior of amino acids and their derivatives. It can be used to investigate the effects of different modifications on the chemical and physical properties of L-lysine, as well as to explore the potential applications of these modified compounds in various fields.

InChI:InChI=1/C20H30N2O6/c1-20(2,3)28-18(24)21-13-9-8-12-16(17(23)26-4)22-19(25)27-14-15-10-6-5-7-11-15/h5-7,10-11,16H,8-9,12-14H2,1-4H3,(H,21,24)(H,22,25)

Upstream product

• 186581-53-3 diazomethane 
• 2212-76-2 N^α-benzyloxycarbonyl-N^ε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt 
• 67-56-1 methanol 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 2212-75-1 N₂-[(benzyloxy)carbonyl]-L-lysine 
• 2389-60-8 Z-Lys(Boc)-OH 
• 5591-93-5 (S)-methyl 6-amino-2-(benzyloxycarbonylamino)hexanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 13515-95-2 lysine methyl ester dihydrochloride 
• 501-53-1 benzyl chloroformate 
• 74-88-4 methyl iodide 
• 657-27-2 L-Lysine hydrochloride 
• 14511-39-8 2(S)-2-amino-6-(benzylideneamino)hexanoic acid 
• 2418-95-3 (S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid 

Downstream Products

• 5591-93-5 (S)-methyl 6-amino-2-(benzyloxycarbonylamino)hexanoate 
• 122314-13-0 tert-butyl-N-[(5S)-5-(benzyloxycarbonylamino)-6-oxo-hexyl]carbamate 
• 26348-68-5 N-(benzyloxycarbonyl)lysine methyl ester hydrochloride 
• 5591-93-5 (S)-methyl 6-amino-2-(benzyloxycarbonylamino)hexanoate 
• 3017-32-1 (S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate 
• 1401318-34-0 C₂₇H₂₉N₅O₃ 
• 1401318-33-9 C₂₆H₂₉N₅O₄S 
• 1401318-32-8 (S)-benzyl tert-butyl (6-azidohexane-1,5-diyl)dicarbamate 

Relevant academic research and scientific papers

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.

Conjugated TLR7 and/or TLR8 and TLR2 polycationic agonists

The present invention relates to a conjugated compound of Formula I : Q-Z-R4 wherein Q is a TLR7 and/or TLR8 agonist and Z-R4 is a TLR2 agonist, said conjugated compound being chosen among compounds of Formula II :

Conjugated TLR7 and/or TLR8 and TLR2 polycationic agonists

A conjugated compound of Formula I: Q-Z—R4 wherein Q is a TLR7 and/or TLR8 agonist and Z—R4 is a TLR2 agonist, the conjugated compound being chosen among compounds of Formula II:

Novel compositions of TLR7 and/or TLR8 agonists conjugated to lipids

The present invention concerns a conjugated compound of formula Q-Z-R4 wherein Q is a TLR7 and/or TLR8 agonist and Z-R4 is a lipid covalently linked to an amino acid or peptide coupled to a polyamine group, and a process for the manufacture of said conjugated compound, as well as a complex formed between said conjugated compound and a polyanionic molecule and a pharmaceutical composition containing said conjugated compound or complex. The invention further concerns the use of said conjugated compound or complex in the treatment of infection, cancer or immune disorders or for use in vaccines.

COMPOUNDS AND COMPOSITIONS AS CHANNEL ACTlVATING PROTEASE INHIBITORS

The invention provides compounds and pharmaceutical compositions thereof, which are useful for modulating channel activating proteases, and methods for, using such compounds to treat, ameliorate or prevent a condition associated with a channel activating protease, including but not limited to prostasin, PRSS22, TMPRSS11 (e.g., TMPRSS11B, TMPRSS11E), TMPRSS2, TMPRSS3, TMPRSS4 (MTSP-2), matriptase (MTSP-1), CAP2, CAP3, trypsin, cathepsin A, or neutrophil elastase.

Prenyl carbamates: Preparation and deprotection

Prenyloxycarbonylimidazole (PreocIm) and prenyl p-nitrophenyl carbonate (PreocOC6H4p-NO2), two substitutes for the unstable prenyl chloroformate, allowed an efficient introduction of the prenyloxycarbonyl group to a variety of primary and secondary amines. Deprotection of prenyl carbamates was readily achieved by, first their conversion to 2-iodo-3-methoxy-3-methylbutyl carbamates with iodine in methanol followed by reductive β-elimination with zinc powder. These reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic ethers.

Unique overlap in the prerequisites for thrombin inhibition and oral bioavailability resulting in potent oral antithrombotics

Despite intense research over the last 10 years, aided by the availability of X-ray structures of enzyme-inhibitor complexes, only very few truly orally active thrombin inhibitors have been found. We conducted a comprehensive study starting with peptide transition state analogues (TSA). Both hydrophobic nonpeptide analogues as well as hydrophilic peptidic analogues were synthesized. The bioavailability in rats and dogs could be drastically altered depending on the overall charge distribution in the molecule. Compound 27, a tripeptide TSA inhibitor of thrombin, showed an oral bioavailability of 32% in rats and 71% in dogs, elimination half-lives being 58 and 108 min, respectively. The thrombin inhibition constant of compound 27 was 1.1 nM, and in an in vivo arterial flow model, the ED50 was 5.4 nmol/kg.min, comparable to known non-TSA inhibitors. A molecular design was found that combines antithrombotic efficiency with oral bioavailability at low dosages.

Synthesis of lysine-containing fragments of the Proteus mirabilis O27 O-specific polysaccharide and neoglycoconjugates therefrom

Amide-linked lysine mono- and di-uronic acid fragments of the O-specific polysaccharide from P. mirabilis O27 have been synthesised.Nε-Boc-L-lysine tert-butyl ester was condensed with 2-azidoethyl glycosides of glucuronic acid and β-D-GlcpNAc-(1->3)-β-D-GlcpA.Transformation of the products into 2-acrylamidoethyl glycosides, followed by deprotection using trifluoroacetic acid, gave the target monomers that were converted into high-molecular-weight copolymer-type neoglycoconjugates.

Synthesis of a Novel Class of Peptides: Dilactam-Bridged Tetrapeptides

As model compounds for the study of constrained peptides, the following lactam-bridged derivatives were synthesized: Ac-L--D--NHMe (I), Ac-L--L--NHMe (II), Ac-L--NHMe (III), Ac-L--D--NHMe (IV), Ac-L--L--NHMe (V), and Ac-L--NHMe (VI).Benzyloxycarbonyl and tert-butyloxycarbonyl groups were employed for amine protection and the benzyl and methyl esters for carboxyl protection.Coupling reactions were carried out by the use of active esters or through azide activation.Cyclization reactions were carried out by adding the active ester hydrochlorides into large volumes of pyridine at elevated temperatures.The cyclic intermediates were obtained in yields of 45-50percent.Fragment condensation of the cyclic dipeptides yielded the corresponding dilactam-bridged tetrapeptides.