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Sachin R Chaudhari et al.
Organic & biomolecular chemistry, 10(31), 6410-6419 (2012-06-28)
The three-component chiral derivatization protocols have been developed for (1)H, (13)C and (19)F NMR spectroscopic discrimination of chiral diacids by their coordination and self-assembly with optically active (R)-α-methylbenzylamine and 2-formylphenylboronic acid or 3-fluoro-2-formylmethylboronic acid. These protocols yield a mixture of
Palladium-Catalyzed ortho-Selective C-H Fluorination of Oxalyl Amide-Protected Benzylamines.
Chen, Changpeng et al.
The Journal of Organic Chemistry, 80(2), 942-949 (2014)
Andrew T Fischer et al.
The journal of physical chemistry. B, 111(28), 8187-8196 (2007-06-23)
Speed-of-sound measurements are reported for RS (racemic) and S liquid alpha-methylbenzylamine (MBA) obtained using a modified design of previously published experimental geometry. After correcting for density changes, the resulting isentropic compressibility of the S liquid is found to be 2%
Tran Quoc Trung et al.
Archives of pharmacal research, 29(1), 108-111 (2006-02-24)
The economic and effective method for preparation of R-(-)-ibuprofen by diastereomer crystallization was developed. R-(-)-ibuprofen was resolved from racemic ibuprofen by forming R-(-)-ibuprofen-R-(+)-alpha-methylbenzylamine diastereomeric salt with R-(+)-alpha(-methylbenzylamine and crystallization. The purity of R-(-)-ibuprofen-R-(+)-alpha-methylbenzylamine diastereomeric salt was tested and confirmed using
Jinzhao Wang et al.
Se pu = Chinese journal of chromatography, 27(3), 376-378 (2009-10-07)
A simple pre-column derivatization-high performance liquid chromatographic (HPLC) method was established for the determination of optical purity of alpha-phenylethylamine. The enantiomers of alpha-phenylethylamine were derivatized with 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate (GITC). The resulted diastereoisomers were separated on an Agilent Zorbax C18 column
Hyungdon Yun et al.
Bioscience, biotechnology, and biochemistry, 72(11), 3030-3033 (2008-11-11)
To produce (S)-alpha-methylbenzylamine (MBA) from acetophenone, recombinant Escherichia coli co-expressing omega-transaminase and acetolactate synthase was used as a whole-cell biocatalyst. The solvent-bridge reaction system increased the yield of the whole-cell reaction by 2.5-fold, and the inhibitory (S)-alpha-MBA produced in the
Jan Dines Knudsen et al.
Microbial cell factories, 15, 37-37 (2016-02-18)
Saccharomyces cerevisiae can be engineered to perform a multitude of different chemical reactions that are not programmed in its original genetic code. It has a large potential to function as whole-cell biocatalyst for one-pot multistep synthesis of various organic molecules
Kinetic resolution of ??methylbenzylamine with o?transaminase screened from soil microorganisms: Application of a biphasic system to overcome product inhibition.
Shin, Jong-Shik and Kim, Byung-Gee
Biotechnology and Bioengineering, 55(2), 348-358 (1997)
Shao-Hua Huang et al.
Magnetic resonance in chemistry : MRC, 47(5), 423-427 (2009-02-19)
Two types of chiral analytes, the urea and amide derivatives of alpha-phenylethylamine, were prepared. The effect of inter-molecular hydrogen-bonding interaction on self-discrimination of the enantiomers of analytes has been investigated using high-resolution (1)H NMR. It was found that the urea
Sarah A Almahboub et al.
Applied microbiology and biotechnology, 102(2), 789-799 (2017-11-28)
Terminal modification of peptides is frequently used to improve their hydrophobicity. While N-terminal modification with fatty acids (lipidation) has been reported previously, C-terminal lipidation is limited as it requires the use of linkers. Here we report the use of a
Karim Engelmark Cassimjee et al.
Organic & biomolecular chemistry, 10(28), 5466-5470 (2012-06-13)
For biocatalytic production of pharmaceutically important chiral amines the ω-transaminase enzymes have proven useful. Engineering of these enzymes has to some extent been accomplished by rational design, but mostly by directed evolution. By use of a homology model a key
Takahiro Takayama et al.
Analytica chimica acta, 898, 73-84 (2015-11-04)
Chiral metabolites are found in a wide variety of living organisms and some of them are understood to be physiologically active compounds and biomarkers. However, the overall analysis of chiral metabolomics is quite difficult due to the high number of
Yan-Song Zheng et al.
Chemical communications (Cambridge, England), (32)(32), 3398-3400 (2007-11-21)
Chiral para-tert-butylcalix[4]arene bearing (S)-alpha-methylbenzylamine groups at lower rim only self-assembles with one of two enantiomers of 2,3-dibenzoyltartaric acid into coiled nanofibers and the coiled nanofibers only stack with the nanofibers having the same handedness to construct bigger ribbon-like fibers bearing
Manuel Algarra et al.
Journal of separation science, 33(2), 143-154 (2009-12-31)
Free fatty acids were derivatized as amides (DFFA) by reaction with (R)-(+)-1-phenylethylamine, using a simple, fast and robust reaction scheme. A HPLC method with diode array and ESI MS detection was developed for the analysis of the derivatized substances. Six
C Claaßen et al.
ChemCatChem, 12(4), 1190-1199 (2020-03-21)
Online analytics provides insights into the progress of an ongoing reaction without the need for extensive sampling and offline analysis. In this study, we investigated benchtop NMR as an online reaction monitoring tool for complex enzyme cascade reactions. Online NMR
Hans-Jürgen Federsel et al.
Accounts of chemical research, 40(12), 1377-1384 (2007-08-03)
This Account describes the design and development of a scalable synthesis for the drug molecule AR-A2 (1) starting from the discovery route originating in medicinal chemistry. Special emphasis is placed on the introduction of the correct (R) stereochemistry on C2
Maria Cammenberg et al.
Chembiochem : a European journal of chemical biology, 7(11), 1745-1749 (2006-09-23)
One of the commercial methods for preparing enantiopure amines is lipase-catalyzed kinetic resolution, although lipases catalyze aminolysis with only low activity. Interestingly, in 1997 Balkenhohl et al. used ethyl methoxyacetate instead of ethyl butyrate as an acylation reagent for the
R Moaddel et al.
Chirality, 17(8), 501-506 (2005-08-23)
A liquid chromatography stationary phase containing immobilized membranes obtained from a cell line that expresses the human organic cation transporter (hOCT1-IAM) has been used to study the binding of the enantiomers of propranolol, atenolol, pseudoephedrine, and alpha-methylbenzylamine to the immobilized
Abraham R Martin et al.
Applied microbiology and biotechnology, 76(4), 843-851 (2007-06-22)
Enzyme immobilization often improves process economics, but changes in kinetic properties may also occur. The immobilization of a recombinant thermostable (S)-aminotransferase was made by entrapment on calcium alginate-3% (w/v)-and tested with (S)-(-)-(alpha)-methylbenzylamine for acetophenone production. The best immobilization results were
Moritz Voss et al.
ACS chemical biology, 15(2), 416-424 (2020-01-29)
The enzymatic transamination of ketones into (R)-amines represents an important route for accessing a range of pharmaceuticals or building blocks. Although many publications have dealt with enzyme discovery, protein engineering, and the application of (R)-selective amine transaminases [(R)-ATA] in biocatalysis
Antoine Fadel et al.
The Journal of organic chemistry, 72(5), 1780-1784 (2007-01-30)
Enantiomerically pure (R)-(+)-pipecolic acid was synthesized in four steps and 42% overall yield starting from dihydropyran and (R)-alpha-methylbenzylamine. A general short strategy is also described for preparing (S)-proline (47.5% overall yield) and derivatives.
Christian Merten et al.
Chirality, 22(8), 754-761 (2010-02-27)
Chiral alpha-methylbenzyl amine is a well known and often used chiral auxiliary, e.g., in the resolution of racemates or asymmetric catalysis. In this work, alpha-methylbenzyl amine and its derivatives N,alpha-dimethylbenzyl amine, N,N,alpha-trimethylbenzyl amine, and bis[alpha-methylbenzyl] amine were investigated by vibrational
Alejandra León et al.
Journal of natural products, 75(5), 859-864 (2012-05-12)
The enantiomeric lactams (-)-8, (+)-8, (+)-9, and (-)-9 were formed by the reaction of the dimeric phthalide rac-tokinolide B (rac-3) with (R)-(+)-α-methylbenzylamine and (S)-(-)-α-methylbenzylamine. The absolute configurations of compounds 8 and 9 were assigned by experimental and theoretically calculated electronic
Barry Lygo et al.
Organic & biomolecular chemistry, 10(25), 4968-4976 (2012-05-23)
A short synthetic route to diastereoisomeric atropos dihydro-5H-dibenz[c,e]azepinium salts via reaction of a single enantiomer of (R)-α-methylbenzylamine with a racemic atropos biphenol derivative is described. Compounds prepared via this approach are used to provide strong evidence that structurally related tropos
Bor-Yann Chen et al.
Applied biochemistry and biotechnology, 191(1), 59-73 (2020-01-29)
This first-attempt study used electrochemical methods to quantitatively assess electron-shuttling capabilities of different neurotransmitters crucial to catecholamine biosynthesis in human brain. As prior studies mentioned, aromatics bearing ortho- or para-dihydroxybenzenes could reveal promising electroactivities to stimulate bioenergy generation in microbial
Ignacio Caretti et al.
Physical chemistry chemical physics : PCCP, 13(45), 20427-20434 (2011-10-14)
Single enantiomers of R-/S-methylbenzylamine (MBA) were found to selectively form adducts with the chiral non-C(2) symmetric Cu-salen complex N-(3,5-di-tert-butylsalicylidene)-N'-(salicylidene)-cyclohexane-1,2-diamine copper(II), hereafter labelled [Cu(3)]. The g/A spin Hamiltonian parameters of this Cu(II) complex showed a decrease in symmetry from axial to
Boyeong Kang et al.
Scientific reports, 7(1), 4786-4786 (2017-07-08)
The energy flow during natural photosynthesis is controlled by maintaining the spatial arrangement of pigments, employing helices as scaffolds. In this study, we have developed porphyrin-peptoid (pigment-helix) conjugates (PPCs) that can modulate the donor-acceptor energy transfer efficiency with exceptional precision
Paul E Harrington et al.
Current medicinal chemistry, 14(28), 3027-3034 (2008-01-29)
The calcium sensing receptor (CaR) is a G protein-coupled receptor (GPCR) that plays a fundamental role in serum calcium homeostasis. The CaR is expressed on the chief cells of the parathyroid gland and is responsible for controlling the secretion of
Nora Weber et al.
Microbial cell factories, 16(1), 3-3 (2017-01-05)
Whole-cell biocatalysis based on metabolically active baker's yeast with engineered transamination activity can be used to generate molecules carrying a chiral amine moiety. A prerequisite is though to express efficient ω-transaminases and to reach sufficient intracellular precursor levels. Herein, the
Carlos Fernandes et al.
The Journal of organic chemistry, 74(8), 3217-3220 (2009-03-17)
A short, convenient, gram scale protocol has been established to allow facile access to all four stereoisomers of 2-aminocyclobutanecarboxylic acid, each in enantiomerically pure form (ee >99%). Starting from the readily available cis racemate, the procedure combines efficient alpha-phenylethylamine derivative
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