16259-78-2

Usage

Uses

Used in Pharmaceutical Industry:
H-LYS-OBZL 2 P-TOSYLATE is used as a building block for the preparation of peptide-based drugs and pharmaceuticals. Its selective reactivity and protection groups make it suitable for the synthesis of complex peptide structures.
Used in Biochemical Research and Analysis:
H-LYS-OBZL 2 P-TOSYLATE is utilized in biochemical research and analysis for the study of peptide synthesis and the development of new methodologies in organic synthesis. Its unique structure and properties allow for selective reactions and transformations, facilitating the synthesis of complex organic molecules.
Used in Organic Synthesis:
H-LYS-OBZL 2 P-TOSYLATE is used as an important intermediate in organic synthesis. The tosylate group serves as a good leaving group, making it useful for selective reactions and transformations in the synthesis of various organic compounds.

InChI:InChI=1/C13H20N2O2.2C7H8O3S/c14-9-5-4-8-12(15)13(16)17-10-11-6-2-1-3-7-11;2*1-6-2-4-7(5-3-6)11(8,9)10/h1-3,6-7,12H,4-5,8-10,14-15H2;2*2-5H,1H3,(H,8,9,10)/t12-;;/m0../s1

Upstream product

• 56-87-1 L-lysine 
• 104-15-4 toluene-4-sulfonic acid 
• 100-51-6 benzyl alcohol 

Downstream Products

• 1173377-86-0 Nα-Nε-bis[3-(N-octanoyl)aminopropanoyl]-L-lysine benzyl ester 
• 63663-24-1 Nα-Nε-didodecanoyl-L-lysine benzyl ester 
• 1173377-69-9 Nα-Nε-bis[3-(N-dodecanoyl)aminopropanoyl]-L-lysine benzyl ester 
• 1173377-77-9 Nα-Nε-bis[3-(N-decanoyl)aminopropanoyl]-L-lysine benzyl ester 
• 258875-40-0 N^α,N^ε-bis(hexadecanoyl)-N-[2-(benzyloxycarbonyl)ethyl]-L-lysinamide 
• 258875-39-7 N^α,N^ε-bis(hexadecanoyl)-L-lysine benzyl ester 

Relevant academic research and scientific papers

Synthesis and assembly of poly(ethylene glycol) - Lipids with mono-, di-, and tetraacyl chains and a poly(ethylene glycol) chain of various molecular weights

We synthesized a series of amphiphiles with poly(ethylene glycol) [MW 2000 (PEG20), 5000 (PEG50), 12 500 (PEG125)] as a headgroup and one, two, or four palmitoyl chains (1C16, 2C16, or 4C16), using a lysine monodendron as a connector. The relationship between the hydrophilic - hydrophobic balance of the multiacyl PEG-lipids and the physicochemical characteristics in self- or co-assembly with phospholipids were studied. The PEG-lipids were easily synthesized by combination of a general liquid-phase peptide synthesis and the acylation of an amino acid. The PEG part of the PEG - lipid films was crystallized to show a typical spherulite pattern. The thermal properties and microscopic observation revealed the phase separation of PEG and acyl chain parts. The critical micelle concentrations (cmcs) mainly depend on the number of acyl chains rather than the molecular weight of the PEG chain, although the area per molecule is dependent on the molecular weight of the PEG chain rather than the number of the acyl chains. The gel-to-liquid crystalline phase transition temperature was increased with the increasing number of acyl chains and the decreasing molecular weight of the PEG chain. The PEG - lipids in the aqueous dispersions assemble to take fibrous structures with bimolecular thickness because of the intermolecular hydrogen bonding. The PEG - lipids were immobilized onto the surface of the phospholipid vesicles by simply adding their aqueous dispersions to the vesicle dispersion; however, they dissociated from the vesicles on dilution of the mixed dispersion because they were incorporated into the vesicles in an equilibrium state. To prevent the dissociation of the PEG - lipids, at least two and four acyl chains were required for PEG with MW 5000 and 12 500, respectively. The aggregation of the vesicles by the addition of water-soluble polymers was significantly inhibited with the increasing molecular weight of the PEG chain. For the tight immobilization of the PEG - lipids with the long PEG chain onto the vesicular surface, an increased number of acyl chains is necessary, and the surface modification with the long PEG chains significantly increases the dispersion stability of the vesicles.

One-step preparation of enantiopure l- or d-amino acid benzyl esters avoiding the use of banned solvents

The enantiomers of amino acid benzyl esters are very important synthetic intermediates. Many of them are currently prepared by treatment with benzyl alcohol and p-toluenesulfonic acid in refluxing benzene or carbon tetrachloride, to azeotropically remove water, and then precipitated as tosylate salt by adding diethyl ether. Here, we report a very efficient preparation of eight l- or d-amino acid benzyl esters (Ala, Phe, Tyr, Phg, Val, Leu, Lys, Ser), in which these highly hazardous solvents are dismissed using cyclohexane as a water azeotroping solvent and ethyl acetate to precipitate the tosylate salt. With some work-up modifications and lower yield, the procedure can be applied also to methionine. Chiral HPLC analysis shows that all the benzyl esters, including the highly racemizable ones such as those of phenylglycine, tyrosine and methionine, are formed enantiomerically pure under these new reaction conditions thus validating the solvents replacement. Contrariwise, toluene cannot be used in place of benzene or carbon tetrachloride because leading to partially or totally racemized amino acid benzyl esters depending on the polar effect of the amino acid α-side chain as expressed by Taft’s substituent constant (σ*).

POLY(ESTER UREA) POLYMERS AND METHODS OF USE

The invention provides high molecular weight, crystalline or semi crystalline biodegradable and biocompatible poly(ester urea) (PEU) polymers useful for making vascular stents and hard tissue replacement implants, such as bone substitutes. The PE polymers are based on α amino acids and are made by a polycondensation reaction. PE polymer compositions can contain a therapeutic diol incorporated into the polymer backbone that is released from such an implant in situ. Bioactive agents, such as analgesics, antibiotics, and the like, can also be covalently attached to certain PEU polymers for release into tissue surrounding an implant during biodegradation of the polymer.