Enzyme-catalysed enantioselective hydrolysis of racemic naproxen nitrile.

Abstract:

:The bacterial strain Rhodococcus butanica (ATCC 21197), which exhibits nitrilase and nitrile hydratase/amidase activities, catalyses the enantioselective hydrolysis of racemic naproxen nitrile (R/S)-1 to furnish a moderate enantiomeric excess of (S)-naproxen (S)-3. Racemic naproxen amide (R/S)-2 is not a good substrate for this strain. Resting cells of the newly selected bacterial strain Rhodococcus sp. C3II catalyse the enantioselective hydrolyses of racemic naproxen nitrile (R/S)-1 and naproxen amide (R/S)-2 as well, to give (S)-3 in excellent optical (99% e.e.) and good chemical yields in aqueous medium and in the biphasic system of phosphate buffer/hexane.

journal_name

Bioorg Med Chem

authors

Effenberger F,Böhme J

doi

10.1016/0968-0896(94)85022-4

subject

Has Abstract

pub_date

1994-07-01 00:00:00

pages

715-21

issue

7

eissn

0968-0896

issn

1464-3391

pii

0968-0896(94)85022-4

journal_volume

2

pub_type

杂志文章
  • Model studies for isolation of G-quadruplex-forming DNA sequences through a pull-down strategy with macrocyclic polyoxazole.

    abstract::G-quadruplexes (G4s) are non-B DNA structures present in guanine-rich regions of gene regulatory areas, promoters and CpG islands, but their occurrence and functions remain incompletely understood. Thus, methodology to identify G4 sequences is needed. Here, we describe the synthesis of a novel cyclic hepta-oxazole com...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2019.02.056

    authors: Iida K,Tsushima Y,Ma Y,Sedghi Masoud S,Sakuma M,Yokoyama T,Yoshida W,Ikebukuro K,Nagasawa K

    更新日期:2019-04-15 00:00:00

  • Carbonic anhydrases of anaerobic microbes.

    abstract::Carbonic anhydrases (CAs) catalyze the reversible hydration of carbon dioxide to bicarbonate and are abundantly distributed in prokaryotes and eukaryotes. There are five classes (α,β,γ,δ,ζ) with no significant sequence or structural identity among them, a remarkable example of convergent evolution. The β and γ classes...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.12.005

    authors: Ferry JG

    更新日期:2013-03-15 00:00:00

  • Synthesis and structure-activity relationship of a novel class of 15-membered macrolide antibiotics known as '11a-azalides'.

    abstract::Macrolide antibiotics are widely prescribed for the treatment of respiratory tract infections; however, the increasing prevalence of macrolide-resistant pathogens is a public health concern. Therefore, the development of new macrolide scaffolds with activities against resistant pathogens is urgently needed. An efficie...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.08.007

    authors: Sugimoto T,Tanikawa T,Suzuki K,Yamasaki Y

    更新日期:2012-10-01 00:00:00

  • The influence of hydroquinone on tyrosinase kinetics.

    abstract::In vitro studies, using combined spectrophotometry and oximetry together with hplc/ms examination of the products of tyrosinase action demonstrate that hydroquinone is not a primary substrate for the enzyme but is vicariously oxidised by a redox exchange mechanism in the presence of either catechol, L-3,4-dihydroxyphe...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.05.041

    authors: Stratford MR,Ramsden CA,Riley PA

    更新日期:2012-07-15 00:00:00

  • Biocatalytic combinatorial synthesis.

    abstract::Combinatorial biocatalysis, based on a principle of the combinatorial use of biosynthetic steps rather than the combinatorial use of reagents, offers a complementary approach to combinatorial chemistry, which, used individually or in connection with synthetic organic transformations, provides access to analogues not r...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(99)00145-5

    authors: Krstenansky JL,Khmelnitsky Y

    更新日期:1999-10-01 00:00:00

  • Synthesis and structure–activity relationships of small molecule inhibitors of the simian virus 40 T antigen oncoprotein, an anti-polyomaviral target.

    abstract::Polyomavirus infections are common and relatively benign in the general human population but can become pathogenic in immunosuppressed patients. Because most treatments for polyomavirusassociated diseases nonspecifically target DNA replication, existing treatments for polyomavirus infection possess undesirable side ef...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.09.019

    authors: Ireland AW,Gobillot TA,Gupta T,Seguin SP,Liang M,Resnick L,Goldberg MT,Manos-Turvey A,Pipas JM,Wipf P,Brodsky JL

    更新日期:2014-11-15 00:00:00

  • Rational design, synthesis and biological evaluation of 1,3,4-oxadiazole pyrimidine derivatives as novel pyruvate dehydrogenase complex E1 inhibitors.

    abstract::On the basis of previous study on 2-methylpyrimidine-4-ylamine derivatives I, further synthetic optimization was done to find potent PDHc-E1 inhibitors with antibacterial activity. Three series of novel pyrimidine derivatives 6, 11 and 14 were designed and synthesized as potential Escherichia coli PDHc-E1 inhibitors b...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.03.011

    authors: He H,Wang W,Zhou Y,Xia Q,Ren Y,Feng J,Peng H,He H,Feng L

    更新日期:2016-04-15 00:00:00

  • Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.

    abstract::Tryprostatin A is an inhibitor of breast cancer resistance protein, consequently a series of structure-activity studies on the cell cycle inhibitory effects of tryprostatin A analogues as potential antitumor antimitotic agents have been carried out. These analogues were assayed for their growth inhibition properties a...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.02.050

    authors: Jain HD,Zhang C,Zhou S,Zhou H,Ma J,Liu X,Liao X,Deveau AM,Dieckhaus CM,Johnson MA,Smith KS,Macdonald TL,Kakeya H,Osada H,Cook JM

    更新日期:2008-04-15 00:00:00

  • Synthesis and trypanocidal activity of ent-kaurane glycosides.

    abstract::Novel ent-kaurane glucosides were synthezised by a Koenigs-Knorr reaction between C17 and C19 alcohols derived from kaurenoic acid and 2,3,4,6-tetra-O-acetyl-glucopyranosyl bromide, followed by the hydrolysis of the acetates. Main products were assayed in vitro and in vivo against blood trypomastigote forms of Trypano...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.09.048

    authors: Batista R,Humberto JL,Chiari E,de Oliveira AB

    更新日期:2007-01-01 00:00:00

  • Synthesis and anticonvulsant activity of a class of 2-amino 3-hydroxypropanamide and 2-aminoacetamide derivatives.

    abstract::Several studies have demonstrated that N-substituted amino acid derivatives exhibit weak anticonvulsant activities in vivo. In the present study, a series of amides of aminoacids structurally related to aminoacetamide have been synthesised and investigated for anticonvulsant activity. Among the molecules investigated,...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.12.064

    authors: Ghidini E,Delcanale M,De Fanti R,Rizzi A,Mazzuferi M,Rodi D,Simonato M,Lipreri M,Bassani F,Battipaglia L,Bergamaschi M,Villetti G

    更新日期:2006-05-15 00:00:00

  • Synthesis of 16-(bromoalkyl)-estradiols having inhibitory effect on human placental estradiol 17 beta-hydroxysteroid dehydrogenase (17 beta-HSD type 1).

    abstract::The activity of 17 beta-HSD type 1, the enzyme that converts estrone into its more potent metabolite estradiol, has been demonstrated in all classical steroidogenic tissues and almost all peripheral tissues from both rat and human. Since 17 beta-HSD is one of the most important enzymes involved in active steroid hormo...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/0968-0896(95)00041-e

    authors: Tremblay MR,Auger S,Poirier D

    更新日期:1995-05-01 00:00:00

  • Molecular structure and stereoelectronic properties of herbicide sulphonylureas.

    abstract::MO theoretical calculations were used with the aim to investigate the electronic properties of a number of sulphonylureas 1-8 which are employed as antifeedants. Quantum chemical descriptors [electron density, molecular electrostatic potential (MEP), the topology of frontier orbitals and reactivity index] were determi...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00357-1

    authors: Galeazzi R,Marucchini C,Orena M,Zadra C

    更新日期:2002-04-01 00:00:00

  • Design and synthesis of 6-fluoro-2-naphthyl derivatives as novel CCR3 antagonists with reduced CYP2D6 inhibition.

    abstract::In our previous study on discovering novel types of CCR3 antagonists, we found a fluoronaphthalene derivative (1) that exhibited potent CCR3 inhibitory activity with an IC(50) value of 20 nM. However, compound 1 also inhibited human cytochrome P450 2D6 (CYP2D6) with an IC(50) value of 400 nM. In order to reduce its CY...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.08.006

    authors: Sato I,Morihira K,Inami H,Kubota H,Morokata T,Suzuki K,Iura Y,Nitta A,Imaoka T,Takahashi T,Takeuchi M,Ohta M,Tsukamoto S

    更新日期:2008-09-15 00:00:00

  • Discovery of potent and selective PARP-1 and PARP-2 inhibitors: SBDD analysis via a combination of X-ray structural study and homology modeling.

    abstract::We disclose herein our efforts aimed at discovery of selective PARP-1 and PARP-2 inhibitors. We have recently discovered several novel classes of quinazolinones, quinazolidinones, and quinoxalines as potent PARP-1 inhibitors, which may represent attractive therapeutic candidates. In PARP enzyme assays using recombinan...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.09.061

    authors: Ishida J,Yamamoto H,Kido Y,Kamijo K,Murano K,Miyake H,Ohkubo M,Kinoshita T,Warizaya M,Iwashita A,Mihara K,Matsuoka N,Hattori K

    更新日期:2006-03-01 00:00:00

  • Bisubstrate analogue inhibitors of 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase: New design with improved properties.

    abstract::6-Hydroxymethyl-7,8-dihydropterin pyrophosphokinase (HPPK), a key enzyme in the folate biosynthetic pathway, catalyzes the pyrophosphoryl transfer from ATP to 6-hydroxymethyl-7,8-dihydropterin. The enzyme is essential for microorganisms, is absent from humans, and is not the target for any existing antibiotics. Theref...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.11.032

    authors: Shi G,Shaw G,Liang YH,Subburaman P,Li Y,Wu Y,Yan H,Ji X

    更新日期:2012-01-01 00:00:00

  • Inhibitory activity of a ceramide library on interleukin-4 production from activated T cells.

    abstract::Allergic diseases are hypersensitivity disorders associated with the production of specific immunoglobulin E (IgE) to environmental allergens. Interleukin (IL)-4, produced primarily by CD4(+) T cells, is an important stimulus for the switch of the antibody isotype to IgE in both mice and humans. In this study we inves...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.01.027

    authors: Park J,Li Q,Chang YT,Kim TS

    更新日期:2005-04-01 00:00:00

  • SAR studies of acidic dual γ-secretase/PPARγ modulators.

    abstract::A novel set of dual γ-secretase/PPARγ modulators characterized by a 2-benzyl hexanoic acid scaffold is presented. Synthetic efforts were focused on the variation of the substitution pattern of the central benzene. Finally, we obtained a new class of 2,5-disubstituted 2-benzylidene hexanoic acid derivatives, which act ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.08.003

    authors: Hieke M,Ness J,Steri R,Greiner C,Werz O,Schubert-Zsilavecz M,Weggen S,Zettl H

    更新日期:2011-09-15 00:00:00

  • Synthesis, cytotoxic activity, and SAR analysis of the derivatives of taxchinin A and brevifoliol.

    abstract::Twenty-one derivatives of taxchinin A (1) and brevifoliol (2) were synthesized and evaluated for cytotoxicity against human non-small lung cancer (A549) cell line. Nine derivatives showed potent activity with IC(50) values from 0.48 to 6.22microM. 5-Oxo-13-TBDMS-taxchinin A (11) and 5-oxo-13,15-epoxy-13-epi-taxchinin ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.03.041

    authors: Zhao Y,Guo N,Lou LG,Cong YW,Peng LY,Zhao QS

    更新日期:2008-05-01 00:00:00

  • Comparative reactivity analysis of small-molecule thiol surrogates.

    abstract::Targeted covalent inhibitors represent an increasingly popular approach to modulate challenging drug targets. Since covalent and non-covalent interactions are both contributing to the affinity of these compounds, evaluation of their reactivity is a key-step to find feasible warheads. There are well-established HPLC- a...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115357

    authors: Petri L,Ábrányi-Balogh P,Varga PR,Imre T,Keserű GM

    更新日期:2020-04-01 00:00:00

  • Apoptosis-inducing effect of epolactaene derivatives on BALL-1 cells.

    abstract::Epolactaene, a neuritogenic compound in human neuroblastoma SH-SY5Y, induces apoptosis in a human leukemia B-cell line, BALL-1. The apoptosis-inducing activities of 34 epolactaene derivatives, including those of the newly synthesized alpha-alkyl-alpha,beta-epoxy-gamma-lactam derivative and cyclopropane derivatives, we...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.10.057

    authors: Kuramochi K,Matsui R,Matsubara Y,Nakai J,Sunoki T,Arai S,Nagata S,Nagahara Y,Mizushina Y,Ikekita M,Kobayashi S

    更新日期:2006-04-01 00:00:00

  • A novel class of Plasmodial ClpP protease inhibitors as potential antimalarial agents.

    abstract::The prokaryotic ATP-dependent ClpP protease, localized in the relict plastid of malaria parasite, represents a potential drug target. In the present study, we utilized in silico structure-based screening and medicinal chemistry approaches to identify a novel pyrimidine series of compounds inhibiting P. falciparum ClpP...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.08.049

    authors: Mundra S,Thakur V,Bello AM,Rathore S,Asad M,Wei L,Yang J,Chakka SK,Mahesh R,Malhotra P,Mohmmed A,Kotra LP

    更新日期:2017-10-15 00:00:00

  • Interaction between double helix DNA fragments and a new topopyrone acting as human topoisomerase I poison.

    abstract::A water soluble derivative (2) of topopyrones was selected for NMR studies directed to elucidate the mode of binding with specific oligonucleotides. Topopyrone 2 can intercalate into the CG base pairs, but the residence time into the double helix is very short and a fast chemical exchange averaging occurs at room temp...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.12.005

    authors: Scaglioni L,Mazzini S,Mondelli R,Dallavalle S,Gattinoni S,Tinelli S,Beretta GL,Zunino F,Ragg E

    更新日期:2009-01-15 00:00:00

  • Induction of enantio-selective apoptosis in human leukemia HL-60 cells by (S)-erypoegin K, an isoflavone isolated from Erythrina poeppigiana.

    abstract::Erypoegin K, an isoflavone isolated from the stem bark of Erythrina poeppigiana, has potent apoptosis-inducing effect on human leukemia HL-60 cells. Erypoegin K has a chiral carbon at the C-2'' position of its furan ring and naturally occurs as a racemic mixture of (S)- and (R)-isomers. In the present study, we semi-s...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115490

    authors: Hikita K,Saigusa S,Takeuchi Y,Matsuyama H,Nagai R,Kato K,Murata T,Tanaka H,Wagh YS,Asao N,Kaneda N

    更新日期:2020-06-01 00:00:00

  • Anti-tubercular activities of 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine analogues endowed with high activity toward non-replicative Mycobacterium tuberculosis.

    abstract::Thirty three derivatives of 2-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine analogues were synthesized by molecular modification of a reported antimycobacterial molecule (GSK163574A). Compounds were evaluated in vitro against actively replicative and nutrient starved non-replicative Mycobacter...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.09.012

    authors: Samala G,Brindha Devi P,Saxena S,Gunda S,Yogeeswari P,Sriram D

    更新日期:2016-11-01 00:00:00

  • Active core structure of terfestatin A, a new specific inhibitor of auxin signaling.

    abstract::The auxins, plant hormones, regulate many aspects of the growth and development of plants. Terfestatin A (TrfA), a novel auxin signaling inhibitor, was identified in a screen of Streptomyces sp. F40 extracts for inhibition of the expression of an auxin-inducible gene. However, the mode of action of TrfA has not been e...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.02.085

    authors: Hayashi K,Yamazoe A,Ishibashi Y,Kusaka N,Oono Y,Nozaki H

    更新日期:2008-05-01 00:00:00

  • Synthesis of oligodeoxynucleotides incorporating 2-N-carbamoylguanine and evaluation of the hybridization properties.

    abstract::Previously, we reported 2-N-carbamoylguanine (cmG) as a guanine analog. We further studied the synthetic protocol and hybridization properties of oligodeoxynucleotides (ODNs) incorporating cmG. These ODNs were synthesized using the phosphoramidite of cmG without protection of the 6-O position. However, the isolated pr...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.11.042

    authors: Sasami T,Odawara Y,Ohkubo A,Sekine M,Seio K

    更新日期:2009-02-01 00:00:00

  • Screening helix-threading peptides for RNA binding using a thiazole orange displacement assay.

    abstract::The fluorescent intercalator displacement assay using thiazole orange has been adapted to the study of RNA-binding helix-threading peptides (HTPs). This assay is highly sensitive with HTP-binding RNAs and provides binding affinity data in good agreement with quantitative ribonuclease footprinting without the need for ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.08.066

    authors: Krishnamurthy M,Schirle NT,Beal PA

    更新日期:2008-10-01 00:00:00

  • Structural studies of β-hairpin peptidomimetic antibiotics that target LptD in Pseudomonas sp.

    abstract::We report structural studies in aqueous solution on backbone cyclic peptides that possess potent antimicrobial activity specifically against Pseudomonas sp. The peptides target the β-barrel outer membrane protein LptD, which plays an essential role in lipopolysaccharide transport to the outer membrane. The peptide L27...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.07.013

    authors: Schmidt J,Patora-Komisarska K,Moehle K,Obrecht D,Robinson JA

    更新日期:2013-09-15 00:00:00

  • Design, synthesis and biological evaluation of cycloalkyl arylpyrimidines (CAPYs) as HIV-1 NNRTIs.

    abstract::A series of 18 cycloalkyl arylpyrimidines (CAPYs) were designed from lead compounds diarylpyrimidines (DAPYs), synthesized and evaluated for in vitro anti-HIV activity. Among them, the compound 1p displayed potent anti-HIV-1 activity against WT HIV-1 with an EC(50) value of 0.055 μM and a selectivity index (SI) >7290....

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.10.002

    authors: Gu SX,Yang SQ,He QQ,Ma XD,Chen FE,Dai HF,Clercq ED,Balzarini J,Pannecouque C

    更新日期:2011-12-01 00:00:00

  • Search for new pharmacophores for antimalarial activity. Part II: synthesis and antimalarial activity of new 6-ureido-4-anilinoquinazolines.

    abstract::Synthesis of new 6-ureido-4-anilinoquinazolines have been accomplished and their in vitro antimalarial activity against chloroquine-sensitive P. falciparum have been examined. Out of 64 compounds evaluated, the IC(50) of 16 compounds which have displayed MIC of 0.25 microg/mL were also recorded. One of the compounds (...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.11.005

    authors: Madapa S,Tusi Z,Mishra A,Srivastava K,Pandey SK,Tripathi R,Puri SK,Batra S

    更新日期:2009-01-01 00:00:00