- Enantioselective Cascade Biocatalysis for Deracemization of Racemic β-Amino Alcohols to Enantiopure (S)-β-Amino Alcohols by Employing Cyclohexylamine Oxidase and ω-Transaminase
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Optically active β-amino alcohols are very useful chiral intermediates frequently used in the preparation of pharmaceutically active substances. Here, a novel cyclohexylamine oxidase (ArCHAO) was identified from the genome sequence of Arthrobacter sp. TYUT010-15 with the R-stereoselective deamination activity of β-amino alcohol. ArCHAO was cloned and successfully expressed in E. coli BL21, purified and characterized. Substrate-specific analysis revealed that ArCHAO has high activity (4.15 to 6.34 U mg?1 protein) and excellent enantioselectivity toward the tested β-amino alcohols. By using purified ArCHAO, a wide range of racemic β-amino alcohols were resolved, (S)-β-amino alcohols were obtained in >99 % ee. Deracemization of racemic β-amino alcohols was conducted by ArCHAO-catalyzed enantioselective deamination and transaminase-catalyzed enantioselective amination to afford (S)-β-amino alcohols in excellent conversion (78–94 %) and enantiomeric excess (>99 %). Preparative-scale deracemization was carried out with 50 mM (6.859 g L?1) racemic 2-amino-2-phenylethanol, (S)-2-amino-2-phenylethanol was obtained in 75 % isolated yield and >99 % ee.
- Zhang, Jian-Dong,Chang, Ya-Wen,Dong, Rui,Yang, Xiao-Xiao,Gao, Li-Li,Li, Jing,Huang, Shuang-Ping,Guo, Xing-Mei,Zhang, Chao-Feng,Chang, Hong-Hong
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p. 124 - 128
(2020/09/21)
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- A practical method for the synthesis of highly enantioenriched trans -1,2-amino alcohols
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A highly enantioselective addition of phenyl carbamate to meso-epoxides has been developed to efficiently generate protected trans-1,2-amino alcohols. This transformation is promoted by an oligomeric (salen)Co-OTf catalyst and has been used to prepare two useful 2-aminocycloalkanol hydrochlorides in enantiopure form on a multigram scale from commercially available starting materials.
- Birrell, James A.,Jacobsen, Eric N.
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supporting information
p. 2895 - 2897
(2013/07/26)
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- Cyclic trans-β-amino alcohols: Preparation and enzymatic kinetic resolution
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Enantioenriched cyclic β-amino alcohols, trans-2-aminocyclohexanols (ee, >99%), trans-2-aminocyclopentanols (ee, >99%), trans-1-amino-2- indanols (ee, >99%) and trans-2-amino-1-indanols (ee, ～98%) were prepared in high yields via an Arthrobacter sp. Lipase/PLAP catalyzed kinetic resolution of racemic phthalimido acetates. The addition of toluene as a co-solvent dramatically improved the hydrolysis and enantioselectivity, whereas for indanols, substrate immobilization on Celite improved the efficacy of the kinetic resolution.
- Rouf, Abdul,Gupta, Pankaj,Aga, Mushtaq A.,Kumar, Brijesh,Parshad, Rajinder,Taneja, Subhash C.
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p. 2134 - 2143
(2012/05/04)
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- Resolution of racemic 2-aminocyclohexanol derivatives and their application as ligands in asymmetric catalysis
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A preparatively easy and efficient protocol for the resolution of racemic 2-aminocyclohexanol derivatives is described, delivering both enantiomers with >99% enantiomeric excess (ee) by sequential use of (R)- and (S)-mandelic acid. A simple aqueous workup procedure permits the isolation of the amino alcohols in analytically pure form and the almost quantitative recovery of mandelic acid. Debenzylation of enantiopure trans-2-(N-benzyl)amino-1- cyclohexanol by hydrogenation and subsequent derivatization give access to a broad variety of diversely substituted derivatives. Furthermore, the corresponding cis isomers are readily available. Applications of these optically active aminocyclohexanols in catalyzed asymmetric phenyl transfer reactions to benzaldehydes and transfer hydrogenations of aryl ketones lead to products with up to 96% ee.
- Schiffers, Ingo,Rantanen, Toni,Schmidt, Frank,Bergmans, Werner,Zani, Lorenzo,Bolm, Carsten
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p. 2320 - 2331
(2007/10/03)
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- Process for the production of optically active amino alcohols
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The disclosure describes a process for the preparation of cyclic optically active amino alcohols of formula (I) by reacting an optically active hydroxycarboxylate of formula (IV) with hydrazine to form an optically active hydroxycarboxylic hydrazide compo
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- PYRAZOLOPYRIMIDINES AS CYCLIN-DEPENDENT KINASE INHIBITORS
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In its many embodiments, the present invention provides a novel class of pyrazolo[1,5-a]pyrimidine compounds as inhibitors of cyclin dependent kinases, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the CDKs using such compounds or pharmaceutical compositions.
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- Novel compounds
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The invention provides novel 1,2,3-triazolo[4,5-d]pyrimidine compounds, their use as medicaments, compositions containing them and processes for their preparation.
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- cis-Cyclopentyl PNA (cpPNA) as constrained chiral PNA analogues: stereochemical dependence of DNA/RNA hybridization.
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DNA/RNA hybridization studies of PNA-T oligomers with cis-(1S,2R/1R,2S)-cyclopentyl units in the backbone show stereochemistry dependent binding with RNA/DNA discrimination.
- Govindaraju,Kumar, Vaijayanti A,Ganesh, Krishna N
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p. 860 - 861
(2007/10/03)
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- Lipase-catalyzed Kinetic Resolution of (+/-)-trans- and cis-2-Azidocycloalkanols
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The lipase-catalyzed kinetic resolution of trans- and cis-2-azidocycloalkanols and the preparation of enantiomerically pure trans- and cis-2-aminocycloalkanols are described. Four kinds of lipases were screened for the acetylation of trans- and cis-2-azidocycloalkanols. Among them, Pseudomonas sp. lipases (lipase PS and lipase AK, Amamo Pharmaceutical Co.) showed the highest enantioselectivity. These products were converted to the corresponding 2-aminocycloalkanols to determine their enantiomeric excess (ee) and absolute configurations by HPLC and CD analyses, using (S)-TBMB carboxylic acid [(S)-2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid] as the chiral conversion reagent. The results of the CD analysis proved N,O-bis-(S)-TBMB carboxylated cis-2-aminocycloalkanols to adopt a predominantly N-equatorial conformation. The partially resolved trans- and cis-2-aminocycloalkanols, except for trans-2-aminocyclopentanol, were recrystallized from ethyl acetate to give enantiomerically pure forms.
- Ami, Ei'ichi,Ohrui, Hiroshi
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p. 2150 - 2156
(2007/10/03)
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- Bioreduction of 2-oxocyclopentanecarboxamides: Syntheses of optically active 2-aminomethyl- and 2-aminocyclopentanols
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The fungus Mortierella isabellina NRRL 1757 catalyzes the reduction of 2-oxocyclopentanecarboxamides with very high enantioselectivity giving; in most cases, the corresponding enantiopure 2-hydroxycyclopentanecarboxamides. The presence or absence of a sub
- Quiros, Margarita,Rebolledo, Francisca,Gotor, Vicente
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p. 473 - 486
(2007/10/03)
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- CYCLOALKYL AMINE BIS-ARYL SQUALENE SYNTHASE INHIBITORS
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This invention relates to a class of novel polycyclic compounds containing a cycloalkyl ring having substituted there on a primary amine and which is further linked or bridged to two mono- and/or bicyclic rings and which reduces levels of serum cholesterol in the body without significantly reducing mevalonic metabolite synthesis. This invention relates also to pharmacological compositions and method of treatment for lowering serum cholesterol levels using the compounds of this invention
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- N-(2-HYDROXYCYCLOPENTYL)-1-ISOPROPYL-6-METHYLERGOLINE-8-CARBOXAMIDES
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This invention provides N-(2-hydroxycyclopentyl)-1-isopropyl-6-methylergoline-8-carboxamides useful for blocking 5HT 2 receptors in mammals having an excess of serotonin centrally or peripherally. The invention also provides methods for treating sexual dysfunction, hypertension, migraine, vasospasm, thrombosis, ischemia, depression, anxiety, sleep disorders and appetite disorders with a compound of the invention.
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- 2-Substituted-1H-benz(de)-isoquinoline-1,3-(2H)-diones
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Compounds of the following formula STR1 wherein R1 and R2 are independently selected from hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, nitro, cyano, and trifluoromethyl, and R is selected from a triacetyl substituted pentose, pentose, a tetraacetyl substituted hexose, hexose, a hydroxy substituted cycloalkyl of 5 to 7 carbons, STR2 wherein n is 1 or 2 and R3 is hydrogen, an alkali metal or alkaline earth metal ion; are disclosed. These compounds possess useful anti-inflammatory activity.
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