10289-12-0

Basic information

• Product Name: Carbamic acid, [4-(2,5-dioxo-4-oxazolidinyl)butyl]-, phenylmethyl ester
• CAS NO: 10289-12-0
• Molecular Formula: C15H18N2O5
• Molecular Weight: 306.318
• Mol File: 10289-12-0.mol
• Article Data: 72

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [4-(2,5-dioxo-4-oxazolidinyl)butyl]-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [4-(2,5-dioxo-4-oxazolidinyl)butyl]-, phenylmethyl ester(10289-12-0)
• EPA Substance Registry System: Carbamic acid, [4-(2,5-dioxo-4-oxazolidinyl)butyl]-, phenylmethyl ester(10289-12-0)

Safety Data

• Hazardous Substances Data: 10289-12-0(Hazardous Substances Data)

Upstream product

• 405-39-0 N,N'-di-[(phenylmethoxy)carbonyl]-L-lysine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 32302-83-3 N-ε-benzyloxycarbonyl lysine 
• 75-44-5 phosgene 
• 1155-64-2 N₆-[(benzyloxy)carbonyl]-L-lysine 
• 1387552-55-7 C₂₁H₂₄N₂O₆ 
• 116-16-5 1,1,1,3,3,3-hexachloro-propan-2-one 
• 501-53-1 benzyl chloroformate 
• 56-87-1 L-lysine 
• 657-27-2 L-Lysine hydrochloride 
• 503-38-8 trichloromethyl chloroformate 

Downstream Products

• 82876-19-5 (R)-4-[(S)-5-Benzyloxycarbonylamino-1-((R)-1-carboxy-ethylcarbamoyl)-pentylcarbamoyl]-2-octadecanoylamino-butyric acid benzyl ester 
• 82876-17-3 (R)-4-[(S)-5-Benzyloxycarbonylamino-1-((R)-1-carboxy-ethylcarbamoyl)-pentylcarbamoyl]-2-octanoylamino-butyric acid benzyl ester 
• 82876-00-4 H-Lys(Z)-D-AlaOH 
• 59515-43-4 N⁶-benzyloxycarbonyl-DL-lysine ethyl ester; hydrochloride 
• 108-32-7 1,2-propylene cyclic carbonate 
• 55226-85-2 tetra-(N-carbobenzoxy-L-lysine) 

Relevant articles and documents

Fluorinated PEG-Polypeptide Polyplex Micelles Have Good Serum-Resistance and Low Cytotoxicity for Gene Delivery

A novel PEGylation polypeptide, poly(ethylene glycol)-b-poly(l-lysine)-b-poly(l-cysteine) (PEG-PLL-PCys) triblock copolymer is synthesized via the sequential ring-opening polymerization of amino acid N-carboxyanhydrides initiated by methoxypolyethylene gl

Reduction-sensitive amphiphilic dextran derivatives as theranostic nanocarriers for chemotherapy and MR imaging

Reduction-sensitive, amphiphilic dextran derivatives were developed from disulfide-linked dextran-g-poly-(N-ε-carbobenzyloxy-l-lysine) graft polymer (Dex-g-SS-PZLL), and used as theranostic nanocarriers for chemotherapy and MR imaging. Dex-g-SS-PZLLs were

Tandem catalysis: A new approach to polypeptides and cyclic carbonates

A new tandem catalytic system mediates very efficiently and selectively at room temperature two sequential reactions to produce relevant derivatives in one pot. Remarkably, this new concept of catalysis allows the facile synthesis of polypeptides and provides direct access to cyclic carbonates in high yields, through the incorporation of the carbon dioxide released from the initial step, thus achieving full-atom economy.

On-POM Ring-Opening Polymerisation of N-Carboxyanhydrides

The ring-opening polymerisation of α-amino acid N-carboxyanhydrides (NCAs) offers a simple and scalable route to polypeptides with predicted and narrow molecular weight distributions. Here we show how polyoxometalates (POMs)—redox-active molecular metal-oxide anions—can serve as inorganic scaffold initiators for such NCA polymerisations. This “On-POM polymerisation” strategy serves as an innovative platform to design hybrid materials with additive or synergistic properties stemming from the inorganic and polypeptide component parts. We have used this synthetic approach to synthesise a library of bactericidal poly(lysine)–POM hybrid derivatives that can be used to prevent biofilm formation. This versatile “On-POM polymerisation” method provides a flexible synthetic approach for combining inorganic scaffolds with amino acids, and the potential to tailor and improve the specificity and performance of hybrid antimicrobial materials.

High potency and broad-spectrum antimicrobial peptides synthesized via ring-opening polymerization of α-Aminoacid-N-carboxyanhydrides

Antimicrobial peptides (AMPs), particularly those effective against methicillin-resistant Staphylococcus aureus (S. aureus) and antibiotic-resistant Pseudomonas aeruginosa (P. aeruginosa), are important alternatives to antibiotics. Typical peptide synthesis methods involving solid-phase sequential synthesis are slow and costly, which are obstacles to their more widespread application. In this paper, we synthesize peptides via ring-opening polymerization of α-amino acid N-carboxyanhydrides (NCA) using a transition metal initiator. This method offers high potential for inexpensive synthesis of substantial quantities of AMPs. Lysine (K) was chosen as the hydrophilic amino acid and alanine (A), phenylalanine (F), and leucine (L) as the hydrophobic amino acids. We synthesized five series of AMPs (i.e., P(KA), P(KL), P(KF), P(KAL), and P(KFL)), varied the hydrophobic amino acid content from 0 to 100%, and determined minimal inhibitory concentrations (MICs) against clinically important Gramnegative and Gram-positive bacteria and fungi (i.e., Escherichia coli (E. coli), P. aeruginosa, Serratia marcescens (S. marcescens), and Candida albicans (C. albicans). We found that P(K10F 7.5L7.5) and P(K10F15) show the broadest activity against all five pathogens and have the lowest MICs against these pathogens. For P(K10F7.5L7.5), the MICs against E. coli, P. aeruginosa, S. marcescens, S. aureus, and C. albicans are 31 μg/mL, 31 μg/mL, 250 μg/mL, 31 μg/mL, and 62.5 μg/mL, while for P(K10F15) the respective MICs are 31 μg/mL, 31 μg/mL, 250 μg/mL, 31 μg/mL, and 125 μg/mL. These are lower than the MICs of many naturally occurring AMPs. The membrane depolarization and SEM assays confirm that the mechanism of microbe killing by P(K10F 7.5L7.5) copeptide includes membrane disruption, which is likely to inhibit rapid induction of AMP-resistance in pathogens.

A head-to-head comparison of poly(sarcosine) and poly(ethylene glycol) in peptidic, amphiphilic block copolymers

In this work we compare chemical and solution properties, like critical aggregate concentrations (CAC) and hydrodynamic radii of aggregates based on either poly(ethylene glycol) or poly(sarcosine) block copolymers in aqueous solution. The amine functionalized, hydrophilic polymers poly(sarcosine) (degree of polymerization, Xn = 100 and 200) and PEG (Xn = 121 and 242) of comparable hydrodynamic volume were used to initiate the ring opening polymerization of α-amino acid-N-carboxyanhydrides based on ε-benzyl-l-glutamate (Glu(OBn)) or ε-carboxybenzyl-l-lysine (Lys(Z)). The second, hydrophobic block was kept at a degree of polymerization of 25 and 50 to enable a direct comparison of solution properties of block copolymers. In both cases block length could be precisely adjusted and all synthesized block copolymers have narrow molecular weight distributions and dispersities between 1.1 and 1.2. Both types of block copolymers display critical aggregate concentrations in the range of 6?10-8-3?10-7 mol/L and aggregates possess hydrodynamic radii in a range of 40-100 nm. PEG based systems, however, have a slightly lower CAC and tend to form smaller micelles, while PSar based systems have commonly smaller μ2 parameter indication more uniform aggregates.

Molecular Strings Significantly Improved the Gene Transfection Efficiency of Polycations

High transfection efficiency and low cytotoxicity are the two key factors to be considered in the design of gene carriers. Herein, a novel and versatile gene carrier (PLL-RT) was prepared by introducing "molecular string" RT (i.e., p-toluylsulfonyl argini

Novel polypeptide/thiol - SBA-15 hybrid materials synthesized via surface selective grafting

Novel hybrid materials are synthesized through the surface selective grafting of poly-l-lysine and thiols from SBA-15. The Royal Society of Chemistry 2010.

Highly efficient antibacterial diblock copolypeptides based on lysine and phenylalanine

A series of amphiphilic diblock copolypeptides (K30-b-F15, K30-b-F30, and K30-b-F45) were synthesized via N-carboxy-α-amino-anhydride ring-opening polymerization. The copolypeptides had excellent antibacterial efficacy to both Gram positive (S. aureus) and Gram negative (E. coli) bacteria. The minimum inhibitory concentrations (MICs) against E. coli and S. aureus are 8?μg?mL?1 and 2?μg?mL?1, respectively, lower than most natural and artificial antimicrobial peptides (AMPs). The morphological changes of the bacteria treated with diblock copolypeptides were investigated by transmission electron microscopy; the results proved that the diblock copolypeptides had a similar antibacterial pore-forming mechanism to natural cationic peptides. This was confirmed by laser scanning confocal microscope images. CCK-8 results and the MICs showed that the diblock copolypeptides have high selectivity to bacteria, which suggested that the diblock copolypeptides could be excellent candidates to replace traditional antibiotics in future.

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PH-responsive amphiphilic block copolymer prodrug conjugated near infrared fluorescence probe

A novel amphiphilic multi-block copolymer conjugated with both a near infrared fluorescence probe and drug has been designed and prepared by means of ring-opening polymerization (ROP) of N-Carboxy Anhydride (NCA) monomers following a Reversible Addition-F

pH-sensitive polymeric micelles assembled by stereocomplexation between PLLA-b-PLys and PDLA-b-mPEG for drug delivery

pH-responsive stereocomplexed micelles based on poly(l-lactic acid)-b-polylysine/poly(d-lactic acid)-b-methoxy poly(ethylene glycol) (PLLA-b-PLys/PDLA-b-mPEG) were fabricated by stereocomplexation between enantiomeric PLA segments. The morphology, critica

Synthesis of thermo- and pH-sensitive polyion complex micelles for fluorescent imaging

Two thermo- and pH-sensitive polypeptide-based copolymers, poly(N-isopropylacrylamide-co-N-hydroxymethylacrylamide)-b-poly(L-lysine) (P(NIPAAm-co-HMAAm)-b-PLL, P1) and poly(N-isopropylacrylamide-co-N- hydroxymethylacrylamide)-b-poly(glutamic acid) (P(NIPAAm-co-HMAAm)-b-PGA, P2), have been designed and synthesized by the ring-opening anionic polymerization of N-carboxyanhydrides (NCA) with amino-terminated P(NIPAAm-co-HMAAm). It was found that the block copolymers exhibit good biocompatibility and low toxicity. As a result of electrostatic interactions between the positively charged PLL and negatively charged PGA, P1 and P2 formed polyion complex (PIC) micelles consisting of polyelectrolyte complex cores and P(NIPAAm-co-HMAAm) shells in aqueous solution. The thermo- and pH-sensitivity of the PIC micelles were studied by UV/Vis spectrophotometry, dynamic light scattering (DLS), and transmission electron microscopy (TEM). Moreover, fluorescent PIC micelles were achieved by introducing two fluorescent molecules with different colors. Photographs and confocal laser scanning microscopy (CLSM) showed that the fluorescence-labeled PIC micelles exhibit thermo- and pH-dependent fluorescence, which may find wide applications in bioimaging in complicated microenvironments. Copyright

All-active antitumor micelles via triggered lipid peroxidation

Traditional antitumor nanomedicines have been suffering from the poor tumor targeting (ca. 1%) by the enhanced permeability and retention (EPR) effect, and the low drug loading (5%). It was postulated that engineering all-active nanoplatform could increa

Poly(l-lysine) modified zein nanofibrous membranes as efficient scaffold for adhesion, proliferation, and differentiation of neural stem cells

Excellent biocompatibility and bioactivity are necessary requirements for a scaffold for nerve repair and regeneration. Natural plant protein zein was chosen as the primary material and poly(l-lysine), which is composed of common amino acids in the human

Phase-transfer of porphyrins by polypeptide-containing hyperbranched polymers and a novel iron(iii) porphyrin biomimetic catalyst

Water-soluble porphyrins can be phase transferred by the hyperbranched multiarm copolymer PEI-PZLys; good catalytic activities and recyclabilities were observed for oxidation catalyzed by the encapsulated porphyrins. The Royal Society of Chemistry 2009.

Dual-vectors of anti-cancer drugs and genes based on pH-sensitive micelles self-assembled from hybrid polypeptide copolymers

A series of amphiphilic pH-sensitive hybrid polypeptide copolymers, poly(ethylene glycol)-b-poly(L-lysine)-b-poly(L-phenylalanine) (PEG-PLL-PLP) were synthesized. The copolymers could self-assemble into micelles with PLP as the hydrophobic core and PEG-PLL as the hydrophilic shell, as evidenced by 1HNMR and TEM. These micelles exhibited obvious pH response in hydrodynamic diameter and pH-dependent drug release behavior, attributed to the protonation/deprotonation of amino groups in PLL segments. The copolymers could further condense plasmid DNA efficiently. Importantly, the polymer/DNA complexes showed high transfection efficiency in 293T cells under optimized conditions. This study suggested the copolymers may have great potential in both drug and gene delivery. The Royal Society of Chemistry 2011.

Novel shell-cross-linked micelles with detachable PEG corona for glutathione-mediated intracellular drug delivery

A series of novel disulfide-containing triblock copolymers, poly(ethylene glycol)-b-poly(l-lysine)-b-poly(rac-leucine) (PEG-SS-PLys-PLeu), were prepared. In an aqueous solution, the copolymers could self-assemble to form core-shell-corona micelles with a disulfide-linked detachable PEG corona, since the PLys middle shell with primary amine groups was linked by a disulfide-containing cross-linker. The morphology and stability of self-assembled micelles were characterized by TEM, DLS and SEM. In the intracellular environment, the micelles underwent destruction of the cross-linked shell with detachment of the PEG corona due to the cleavage of disulfide bonds, followed by the collapse of micelles. The in vitro drug release in response to GSH was further studied. Interestingly, it was found that the micelles not only exhibited reduced drug loss in extracellular environments, but also drastically accelerated drug release at the cytoplasmic GSH level, leading to enhanced growth inhibition of HeLa cells. The glutathione-responsive micelles might have great potential in intracellular drug delivery.

General method for purification of α-amino acid-N-carboxyanhydrides using flash chromatography

We describe the application of flash column chromatography on silica gel as a rapid and general method to obtain pure α-amino acid-N-carboxyanhydride (NCA) monomers, the widely used precursors for the synthesis of polypeptides, without the need for recrystallization. This technique was effective at removing all common impurities from NCAs and was found to work for a variety of NCAs, including those synthesized using different routes, as well as those bearing either hydrophilic or hydrophobic side chains. All chromatographed NCAs required no further purification and could be used directly to form high molecular weight polypeptides. This procedure is especially useful for the preparation of highly functional and low melting NCAs that are difficult to crystallize and, consequently, to polymerize. This method solves many long-standing problems in NCA purification and provides rapid access to NCAs that were previously inaccessible in satisfactory quality for controlled polymerization. This method is also practical in that it requires less time than recrystallization and often gives NCAs in improved yields.

Useful synthetic method of polypeptides with well-defined structure by polymerization of activated urethane derivatives of α-amino acids

A facile polymerization strategy for synthesis of polypeptides with well-defined structure using urethane derivatives of α-amino acids in the presence of amine is reported. N-(phenoxycarbonyl) α-amino acid was polymerized at 60°C in N,N-dimethyl acetamide

Amphiphilic amino acid copolymers as stabilizers for the preparation of nanocrystal dispersion

The recent advance of particle size engineering in nanometer ranges has widened the formulation opportunities of relatively water-insoluble drugs. However, the 'nanoformulation' suffers from a lack of systematic understanding about the requirements of polymeric stabilizers. Furthermore, the polymers that can be used for the preparation of nanocrystals are so limited that finding a proper stabilizer for a given formulation is often difficult. In this study, amino acid copolymers whose properties can systematically be tailored are developed, and their morphological and compositional effects are investigated. Copolymers containing lysine (K) as their hydrophilic segments, and phenylalanine (F) or leucine (L) as their hydrophobic segments successfully produce stable nanocrystals (200-300 nm) in water, while copolymers of K and alanine (A) could not generate nanosized particles. Not the morphology but the hydrophobicity of copolymers seems to be a critical parameter in the preparation of drug nanocrystals by wet comminution. The effective stabilization performance of copolymers requires the hydrophobic moiety content to be higher than 15 mol%. Comminution for only 5 min is long enough for nanocrystal preparation, and the crystallinity of drug is found intact after the processing.

Reversible PEGylation and Schiff-base linked imidazole modification of polylysine for high-performance gene delivery

Gene carriers made from polylysine are of interest in relation to gene therapy but suffer from the lack of transfection efficiency due to limited stability and endosomal escape ability. To address this problem, we designed and developed Schiff-base linked

PH-induced structural changes of surface immobilized poly(l-lysine) by two-dimensional (2D) infrared correlation study

This paper reports the pH-induced structural changes in the surface immobilized poly(l-lysine) (PLL) film. Two-dimensional (2D) correlation analysis was applied to the Fourier transform infrared (FTIR) spectra of the surface-immobilized PLL film to examin

Synchrotron small-angle X-ray scattering study of cross-linked polymeric micelles

Polymeric micelles of methoxypoly(ethylene glycol)-b-poly(lactide) containing lysine units (mPEG- PLA-Lys4) were cross-linked by reacting of lysine moieties with a bifunctional bis(N-hydroxysuccinimide ester). The micelles were characterized in

Immunostimulation of tumor microenvironment by targeting tumor-associated macrophages with hypoxia-responsive nanocomplex for enhanced anti-tumor therapy

Tumor-associated macrophages (TAMs), which dampen the therapeutic efficacy of cancer immunotherapy, are the key players in the immunosuppressive tumor microenvironment (TME). Therefore, reprogramming TAMs into tumoricidal M1 macrophages possesses consider

Cholesteroled polymer (Chol-b-Lys)-based nanoparticles (CL-NPs) confer antibacterial efficacy without resistance

It is imperative to develop innovative and efficient antibacterial agents, on account of the mounting prevalence of complicated infections induced by multidrug-resistant bacteria. In this work, Chol-b-Lys nanoparticles (CL-NPs) with a diameter of 304.9 nm