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Acetals

Acetals are a class of organic compounds containing a central carbon atom bonded to two alkoxy groups.
They are formed by the condensation of aldehydes or ketones with alcohols and have a wide range of applications in organic synthesis, as protecting groups, and in the production of various chemicals.
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Most cited protocols related to «Acetals»

Accurate Head Tracking for MRI

Cited 14 times

The camera was designed by the authors for accurate head tracking during simultaneous MR imaging. To provide high-quality images for photogrammetry, specifications include a frame rate of higher than 80 frames/s; a short exposure time (normally 50–100 s) to minimize motion blur; a global shutter to prevent distortion effects when imaging a moving object; and fixed and stable optics. Camera calibration is performed using bundle adjustment [23] .
To ensure MR compatibility, the CLU enclosure was constructed from acetal and lined with 40 m copper shielding to prevent RF interference while minimizing eddy-current induced vibrations. The copper shield also serves as a heat spreader to ensure adequate surface area for conduction through the acetal enclosure. Images are transferred out of the scanner room using a fiber optic IEEE 1394b connection, rather than via copper cable, to improve MR compatibility. The CLU is powered using a single DC supply via coaxial cable, grounded to the Faraday cage of the scanner room. Charge pumps are used in the CLU to provide the required voltages. On-axis marker illumination is achieved through a half-silvered mirror, built into the CLU enclosure. The optics were designed so that the system can track a marker located anywhere between approx. 5 and 65 cm from the CLU. The optical components are mounted on a ceramic block, to ensure long term stability.
Since MPT tracking is independent of the MRI scanner, the tracking data must be transformed from the camera frame of reference into the scanner frame of reference. This is a trivial operation once the correct transformation matrix is known, but initially this is not the case. For the experiments described in this work, we applied the following method to compute the transformation. An MPT marker was fixed to a phantom and the phantom was imaged while tracking data from the camera were logged to file and averaged. This procedure was repeated 10-15 times, with small (e.g., 10°) rotations applied to the phantom between each scan. The difference between consecutive poses was computed using 3D image registration (for the MRI data) and straightforward quaternion operations (for the tracking data). The transformation between the two coordinate systems was then obtained using a least-squares optimization method, such that the measured pose difference data using the two methods became as consistent as possible (after transformation to the MRI coordinate system). In the 1.5 T and 3 T experiments, this transform was then optimized further by applying the procedure described in [3] (link). In this procedure, the phantom is rotated by 180° with prospective motion correction enabled between scans. The resulting phantom volumes are then approximately aligned, and any residual errors, as determined by image registration, are used to refine the transform. This procedure was not performed at 7 T, due to problems with performing the 180° rotations in long-bore scanner. This one-time calibration procedure per scanner generally takes 1–2 hours. No subject-specific calibration is necessary.

Maclaren J., Armstrong B.S., Barrows R.T., Danishad K.A., Ernst T., Foster C.L., Gumus K., Herbst M., Kadashevich I.Y., Kusik T.P., Li Q., Lovell-Smith C., Prieto T., Schulze P., Speck O., Stucht D, & Zaitsev M. (2012). Measurement and Correction of Microscopic Head Motion during Magnetic Resonance Imaging of the Brain. PLoS ONE, 7(11), e48088.

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Publication 2012

Acetals Copper Electric Conductivity Epistropheus Eye Head Light Photogrammetry Radionuclide Imaging Reading Frames Vibration

Cryopreservation of Endothelial Cell Spheroids

Cited 7 times

For small volume PS or NS studies, 5 ml aliquots of ELS were harvested and mixed 1:1 with a freezing solution (24% Me₂SO, 76% Viaspan v/v) precooled to 4 °C, and once equilibrated (15 min), 80% of the excess CPA supernatant was removed, giving a final volume of 6 ml of 12% Me₂SO, 38% Viaspan, and 50% ELS in culture medium, by volume. Icestart beads (1% w/v) (Asymptote) – sterile insoluble granules – which induce ice nucleation close to the equilibrium melting temperature of the mixture, were added and these sank by gravity to the base of the vial. These vials and the CRF were cooled to 4 °C before 5 vials (containing 6 ml each) were placed in the aluminum module, while 5 were placed into the acetal module (see Fig. 1). The EF600-103 was programmed to cool at 1 °C/min from 4 °C to −80 °C. The samples were held in the EF600-103 at −80 °C for 1 h after the cooling cycle was complete, before being transferred to a −80 °C freezer for 7 days.
The samples were warmed rapidly during 330 s in a 37 °C water bath until all the ice had melted (yielding an approximate warming rate of 15 °C/min). The Me₂SO was diluted out of solution during a 10 min stepwise process with prepared chilled culture medium, with residual ice start granules remaining at the bottom of the tube and easily avoided during decanting. The samples were re-cultured in a 5% CO₂ humidified incubator at 37 °C.

Kilbride P., Morris G.J., Milne S., Fuller B., Skepper J, & Selden C. (2014). A scale down process for the development of large volume cryopreservation. Cryobiology, 69(3), 367-375.

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Publication 2014

Acetals Aluminum ARID1A protein, human Bath COOL-1 protein, human Culture Media Cytoplasmic Granules Gravity Sterility, Reproductive Viaspan

Purification and Characterization of Chicken Muscle Triosephosphate Isomerase

Cited 7 times

Rabbit muscle glycerol 3-phosphate dehydrogenase (GPDH) was purchased from United States Biochemical or MP Biomedicals. Bovine serum albumin (BSA) was from Roche. DEAE Sepharose Fast Flow was from GE Healthcare. D,L-Glyceraldehyde 3-phosphate diethyl acetal (barium salt), dihydroxyacetone phosphate (lithium salt), Dowex 50WX4-200R and NADH (disodium salt) were from Sigma. Triethanolamine hydrochloride and imidazole were from Aldrich. Sodium phosphite (dibasic, pentahydrate) was from Riedel-de Haën (Fluka). [1-¹³C]-Glycolaldehyde (99% enriched with ¹³C at C-1, 0.09 M in water) was purchased from Omicron Biochemicals. D₂O (99.9% D) and DCl (35% w/w, 99.9% D) were from Cambridge Isotope Laboratories. Imidazole was recrystallized from benzene. Water was from a Milli-Q Academic purification system. All other commercially available chemicals were reagent grade or better and were used without further purification.
The plasmid pBSX1cTIM containing the wild-type gene for TIM from chicken muscle (25 (link)) and E. coli strain DF502 (strep^R, tpi^-, and his^-) whose DNA lacks the gene for TIM (26 (link)) were generous gifts from Professor Nicole Sampson. E. coli strain DF502 was transformed with pBSX1cTIM and TIM was expressed and purified according to published procedures with ion exchange chromatography performed on DEAE sepharose (15 (link)). The enzyme obtained from the final column was judged to be homogeneous by gel electrophoresis. The concentration of TIM was determined from the absorbance at 280 nm using an extinction coefficient of 3.2 × 10⁴ M^-1 cm^-1 (27 (link)). The following kinetic parameters were determined for turnover of GAP in 30 mM triethanolamine buffer at pH 7.5 and 25 °C (I = 0.1, NaCl) using a coupled assay (see below): k_cat = 2300 s^-1 and K_m = 0.45 mM (22 (link)).

Go M.K., Amyes T.L, & Richard J.P. (2009). Hydron Transfer Catalyzed by Triosephosphate Isomerase. Products of the Direct and Phosphite-Activated Isomerization of [1-13C]-Glycolaldehyde in D2O. Biochemistry, 48(24), 5769-5778.

Publication 2009

2-diethylaminoethanol Acetals Barium Benzene Biological Assay Buffers Chickens CM 2-3 Dihydroxyacetone Phosphate Dowex Electrophoresis Enzymes Escherichia coli Extinction, Psychological Genes Gifts Glyceraldehyde 3-Phosphate Glycerol-3-Phosphate Dehydrogenase glycolaldehyde imidazole Ion-Exchange Chromatographies Isotopes Kinetics Lithium Muscle Tissue NADH Phosphite Plasmids Rabbits Sepharose Serum Albumin, Bovine Sodium Sodium Chloride Strains triethanolamine triethanolamine hydrochloride

Fabrication of Microscale Drug Delivery Devices

Cited 6 times

Cylindrical, microscale devices with 820 μm (diameter) × 3 mm (length) were manufactured from medical-grade Delrin acetal resin blocks (DuPont) by micromachining (CNC Micro Machining Center, Cameron). This material was selected for its combination of structural rigidity, machinability, and biocompatibility (compliance to ISO 10993-1 and USP Class IV). Circular reservoirs (3 to 30 per device) were shaped on the outer surface of devices in dimensions ranging from 150 to 350 μm (diameter) × 150 to 250 μm (depth). Adjacent reservoirs were positioned 400 to 750 μm apart to prevent the intersection of compounds in tissue. All drugs were purchased in powder form (Selleckchem) and stored according to the manufacturer’s instructions. Cetuximab labeled with Alexa 488 was given by K. D. Wittrup (Massachusetts Institute of Technology). For doses with specific concentrations, compounds in the appropriate amounts were added to PEG-1000 or PEG-1450 (Alfa Aesar) and vortexed for 5 min above its melting point (37°C). For insoluble drugs, a mixture of drug, PEG, and an organic solvent (ethanol or acetone) was heated to ~45°C until completely dissolved (table S1). The solution was placed on a rotary evaporator (Yamato Scientific) for ~30 to 40 min at below respective vapor pressures to completely evaporate the solvent, leaving a homogeneous mixture of drug and PEG. Pure powders and concentrations in PEG were packed in solid form into device reservoirs using a tapered, metal needle (Electron Microscopy Sciences) until the reservoirs were completely filled. Before implantation, the devices were rotated on adhesive tape to remove excess compounds on the exterior of the device.

Jonas O., Landry H.M., Fuller J.E., Santini JT J.r., Baselga J., Tepper R.I., Cima M.J, & Langer R. (2015). An implantable microdevice to perform high-throughput in vivo drug sensitivity testing in tumors. Science translational medicine, 7(284), 284ra57.

Publication 2015

Acetals Acetone Cetuximab delrin Electron Microscopy Ethanol Medical Devices Metals Muscle Rigidity Needles Ovum Implantation Pharmaceutical Preparations polyethylene glycol 1000 Powder Resins, Plant Solvents Tissues Vapor Pressure

Molecular Dynamics Simulations of Micellar Systems

Cited 6 times

To be consistent with the force fields developed in this study, we used an “all-atom” approach to model all micellar systems. RESP charges derived in the section II. 1 were involved in GLYCAM-based MD simulations with the bonded and non-bonded parameters taken from the GLYCAM06 force field version f.64 (link) The 1-4 van der Waals and electrostatic scaling factors were set to 1.0, in agreement with the developer recommendations.64 (link) In the case of the CHARMM-K simulations, we used two sets of parameters to model the sugar headgroup and the exocyclic atom connecting the maltose head and the alkyl chain. For the maltose head we used the parameters of Kuttel et al.53 (link) (a revision of the CHARMM22 force field for sugars of Ha et al.)70 (link) and for the acetal atom those of Reiling et al.54 , which is assigned to an ether oxygen atom type with a partial charge of -0.30 e. These two sets of parameters were previously employed by Bogusz et al.44 ,45 and Konidala et al. 46 (link) in MD simulations of C₈G₁ micelle in water. For the CHARMM-Opt simulations, we used the new set of parameters for hexopyranose66 (link) with optimized parameters for the Φ_H/Ψ_H glycosidic dihedral angles which significantly improves the CHARMM force field for simulations of polysaccharides.67 (link) For the connection between the maltose head and the alkyl chain, we adopted the optimized parameter set for ethers by Lee et al.71 (link) combined with the optimized torsion parameters developed for Et-THP described in the previous section II.2. For all MDs performed with the CHARMM force fields, the alkyl chain of the surfactant was modeled with parameters developed by Klauda et al. for alkanes.72 (link) This contrasts with previous investigations44 ,45 and the work of Konidala et al.46 (link) where for alkyl chain the parameters73 were used. Finally, the TIP3P water model73 was adopted to model the solvent for all the simulations.

Abel S., Dupradeau F.Y., Raman E.P., MacKerell AD J.r, & Marchi M. (2010). Molecular Simulations of Dodecyl-β-maltoside Micelles in Water: Influence of the Headgroup Conformation and Force field Parameters. The journal of physical chemistry. B, 115(3), 487-499.

Publication 2010

Acetals Alkanes Carbohydrates Contrast Media Electrostatics Ethers Glycosides Head Maltose Micelles Oxygen Polysaccharides Respiratory Rate Solvents Sugars Surfactants

Most recents protocols related to «Acetals»

Synthesis of Cephem, Carbacephem, Penem, and Carbapenem Conjugates

Not available on PMC !

Example 14

Cephem Conjugates

Cephem acetal linked β-lactam antibiotic cannabinoid conjugate components are synthesized according to the following Scheme. The starting material [15690-38-7] is converted to a hydroxymethyl intermediate containing a side chain and protecting ester of choice as described in the literature (WO 96/04247). A cannabinoid (CBD) is converted to the O-chloromethyl intermediate via reported conditions (Bioorg. & Med. Chem., 26(2), 386-393; 2018; J. Amer. Chem. Soc., 136(26), 9260-9263; 2014; Faming Zhuanli Shenqing, 105037382, 11 Nov. 2015). The hydroxymethyl and O-chloromethyl intermediates are reacted under previously reported conditions (Tetrahedron, 60(12), 2771-2784; 2004) to generate the acetal link. Removal of the diphenylmethyl ester protecting group gives the product.

[Figure (not displayed)]

Carbacephem Conjugates

Carbacephem acetal linked β-lactam antibiotic cannabinoid conjugate components are synthesized according to the following Scheme. The starting material [177472-75-2] is converted to a hydroxymethyl intermediate containing a side chain and protecting ester of choice as described in the literature (WO 96/04247). A cannabinoid (CBD) is converted to the O-chloromethyl intermediate via reported conditions (Bioorg. & Med. Chem., 26(2), 386-393; 2018; J. Amer. Chem. Soc., 136(26), 9260-9263; 2014; Faming Zhuanli Shenqing, 105037382, 11 Nov. 2015). The hydroxymethyl and O-chloromethyl intermediates are reacted under previously reported conditions (Tetrahedron, 60(12), 2771-2784; 2004) to generate the acetal link. Removal of the diphenylmethyl ester protecting group gives the product.

[Figure (not displayed)]

Penem Conjugates

Penem acetal linked β-lactam antibiotic cannabinoid conjugate components are synthesized according to the following Scheme. A cannabinoid (CBD) is converted to its O-chloromethyl intermediate via reported conditions (Bioorg. & Med. Chem., 26(2), 386-393; 2018; J. Amer. Chem. Soc., 136(26), 9260-9263; 2014; Faming Zhuanli Shenqing, 105037382, 11 Nov. 2015). This intermediate is reacted with a hydroxymethyl penem [88585-78-8] under reported conditions (Tetrahedron, 60(12), 2771-2784; 2004) to form the acetal link. Removal of the silyl ether and allyl ester protecting groups under standard conditions gives the product.

[Figure (not displayed)]

Carbapenem Conjugates

Carbapenem acetal linked β-lactam antibiotic cannabinoid conjugate components are synthesized according to the following Scheme. A cannabinoid (CBD) is converted to its O-chloromethyl intermediate via reported conditions (Bioorg. & Med. Chem., 26(2), 386-393; 2018; J. Amer. Chem. Soc., 136(26), 9260-9263; 2014; Faming Zhuanli Shenqing, 105037382, 11 Nov. 2015). This intermediate is reacted with a hydroxymethyl carbapenem [118990-99-1] under reported conditions (Tetrahedron, 60(12), 2771-2784; 2004) to form the acetal link. Removal of the allyl protecting groups under standard conditions gives the product.

[Figure (not displayed)]

US11877988B2. Conjugate molecules (2024-01-23). Diverse Biotech, Inc. [US]. Inventors: Paul Hershberger [US], Philip Arlen [US].

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Patent 2024

Acetals Cannabinoids carbacephems Carbapenems Esters Ethers Monobactams Penem

Monobactam-Cannabinoid Antibiotic Conjugate Synthesis

Not available on PMC !

Example 18

Monobactam acetal linked β-lactam antibiotic cannabinoid conjugate components are synthesized according to the following Scheme. The starting material [76855-69-1] is deacetylated under reported conditions (Journal of Fluorine Chemistry, 72(2), 255-9; 1995) to give the 2-hydroxy intermediate. This hydroxy group is then alkylated with the O-chloromethyl cannabinoid which is prepared as described in the cephem acetal example in this Application to form the acetal link. Removal of the silyl ether protecting group followed by sulfonation using established conditions gives the product.

[Figure (not displayed)]

US11877988B2. Conjugate molecules (2024-01-23). Diverse Biotech, Inc. [US]. Inventors: Paul Hershberger [US], Philip Arlen [US].

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Patent 2024

Acetals Cannabinoids Ethers Fluorine Monobactams

Monobactam-Cannabinoid Conjugate Synthesis

Not available on PMC !

Example 22

Monobactam aminal linked β-lactam antibiotic cannabinoid conjugate components are synthesized according to the following Scheme. The starting material [76855-69-1] is converted to the corresponding amine under reported conditions (Organic Chemistry: An Indian Journal, 9(6), 229-235; 2013) to give the 2-amino intermediate. This amino group is then alkylated with the O-chloromethyl cannabinoid which is prepared as described in the cephem acetal example in this Application to form the acetal link. Removal of the silyl ether protecting group followed by sulfonation using established conditions gives the product.

[Figure (not displayed)]

US11877988B2. Conjugate molecules (2024-01-23). Diverse Biotech, Inc. [US]. Inventors: Paul Hershberger [US], Philip Arlen [US].

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Patent 2024

Acetals Amines Cannabinoids Ethers Monobactams

Synthesis and Purification of Ethyl Thiocarbamate

Not available on PMC !

Example 11

[Figure (not displayed)]

A solution of acetal (300 g, 1.16 mol) in acetone (3.0 L) was heated to reflux and 4N HCl (250 mL) was added over 1.0 h to the refluxing solution. TLC analysis indicated complete consumption of the starting material. The reaction mixture was concentrated under reduced pressure and phases were separated. The organic phase was diluted with ethyl acetate (1.5 L) and washed with saturated NaHCO₃solution (1.0 L), water (1.0 L) and brine (1.0 L), and then dried over anhydrous Na₂SO₄. All of the aqueous phases were combined and extracted with ethyl acetate. The extracts were combined and dried over anhydrous Na₂SO₄. The organic solutions were filtered and concentrated under reduced pressure. The crude product was triturated with petroleum ether and diethyl ether (5:1) and the resulting solid was collected by vacuum filtration and washed with petroleum ether and ethyl acetate (10:1). The filtrate was concentrated and chromatographed using 0-15% ethyl acetate/petroleum ether to give another crop of desired product. All white to light yellow solids were combined and weighed 40 g (43% yield). ¹H NMR (500 MHz, CDCl₃) δ 10.08-10.06 (m, 1H), 8.53-8.50 (m, 1H), 4.49 (q, J=7.1 Hz, 2H), 1.44 (t, J=7.1 Hz, 3H). MS ESI m/z calcd for C₇H₈NO₃S [M+H]⁺186.01; found 186.01.

US11873281B2. Conjugates of cell binding molecules with cytotoxic agents (2024-01-16). HANGZHOU DAC BIOTECH CO., LTD. [CN], None [US], None [CN], None [CN]. Inventors: R. Yongxin Zhao [US], Yue Zhang [CN], Yourang Ma [CN].

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Patent 2024

1H NMR Acetals Acetone Anabolism Bicarbonate, Sodium brine Crop, Avian ethyl acetate Ethyl Ether Filtration Light naphtha Pressure Vacuum

Synthesis of Monobactam-Cannabinoid Conjugates

Not available on PMC !

Example 26

Monobactam thioacetal linked β-lactam antibiotic cannabinoid conjugate components are synthesized according to the following Scheme. The starting material [76855-69-1] is converted to the thiol silver salt using reported conditions (Shenyang Yaoke Daxue Xuebao, 18(1), 20-22; 2001) to give the 2-SH intermediate. This thiol group is then alkylated with the O-chloromethyl cannabinoid which is prepared as described in the cephem acetal example in this Application to form the thioacetal link. Removal of the silyl ether protecting group followed by sulfonation using established conditions gives the product.

[Figure (not displayed)]

US11877988B2. Conjugate molecules (2024-01-23). Diverse Biotech, Inc. [US]. Inventors: Paul Hershberger [US], Philip Arlen [US].

Full text: Click here

Patent 2024

Acetals Cannabinoids Ethers Monobactams Silver Sodium Chloride Sulfhydryl Compounds

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More about "Acetals"

Acetals are a class of organic compounds featuring a central carbon atom bonded to two alkoxy groups.
These versatile molecules are formed through the condensation of aldehydes or ketones with alcohols, and they find a wide range of applications in organic synthesis, as protective groups, and in the production of various chemicals.
Researchers studying acetals can leverage the power of PubCompare.ai's AI-driven comparison platform to optimize their research protocols.
This intuitive interface enables seamless access to the best acetal protocols and products from literature, preprints, and patents, all in a single, convenient tool.
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