Product identification of non-reducing polyketide synthases with C-terminus methyltransferase domain from Talaromyces stipitatus using Aspergillus oryzae heterologous expression.


:Talaromyces stipitatus ATCC 10500 possesses 17 non-reducing polyketide synthase (NR-PKS) genes. During the course of our functional analysis of PKS genes with a C-terminus methyltransferase domain from T. stipitatus, we expressed tspks2, tspks3 and tspks4 genes in the heterologous host Aspergillus oryzae, respectively. Although the tspks4 transformant gave no apparent product in HPLC analysis, a novel azaphilone pentaketide (3) was identified along with two known related products from the tspks2 transformant. Of four hexaketide products from the tspks3 transformant, two new compounds were identified to be 2-acetyl-7-methyl-3,6,8-trihydroxynaphthalene (4) and its derivative fused with α-methyl-α,β-unsaturated γ-lactone (7).


Bioorg Med Chem Lett


Hashimoto M,Wakana D,Ueda M,Kobayashi D,Goda Y,Fujii I




Has Abstract


2015-04-01 00:00:00














  • Amides of xanthurenic acid as zinc-dependent inhibitors of Lp-PLA(2).

    abstract::AX10185, the phenyl amide of xanthurenic acid, was found to be a sub-100nM inhibitor of Lp-PLA(2). However, in the presence of EDTA the inhibitory activity of AX10185 was extinguished while the enzymatic activity of Lp-PLA(2) did not change. Subsequent metal screening experiments determined the inhibition to be Zn(2+)...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Lin EC,Hu Y,Amantea CM,Pham LM,Cajica J,Okerberg E,Brown HE,Fraser A,Du L,Kohno Y,Ishiyama J,Kozarich JW,Shreder KR

    更新日期:2012-01-15 00:00:00

  • Syntheses of potent Leu-enkephalin analogs possessing beta-hydroxy-alpha,alpha-disubstituted-alpha-amino acid and their characterization to opioid receptors.

    abstract::Novel Leu-enkephalin (Leu-Enk) (1) analogs possessing various types of alpha-substituted serine instead of its glycine residue in the position 2 were synthesized via an efficient O,N-migration method. The binding characteristics of the synthetic analogs using Chinese hamster ovary (CHO) cells expressed cloned rat mu-,...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Horikawa M,Shigeri Y,Yumoto N,Yoshikawa S,Nakajima T,Ohfune Y

    更新日期:1998-08-04 00:00:00

  • Preparation of 5'-deoxy-5'-amino-5'-C-methyl adenosine derivatives and their activity against DOT1L.

    abstract::From a readily available 5-C-Me ribofuranoside, we have realized a reliable route to valuable 5'-deoxy-5'-amino-5'-C-methyl adenosine derivatives at gram scale with confirmed stereochemistry. These adenosine derivatives are useful starting materials for the preparation of 5'-deoxy-5'-amino-5'-C-methyl adenosine deriva...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Liu T,Xie W,Li C,Ren H,Mao Y,Chen G,Cheng M,Zhao D,Shen J,Li J,Zhou Y,Xiong B,Chen YL

    更新日期:2017-11-15 00:00:00

  • Carbazolothiophene-2-carboxylic acid derivatives as endothelin receptor antagonists.

    abstract::The SmI(2)-promoted three-component coupling reaction of thiophene-2-carboxylate, indole-2-carbaldehyde and acetophenone provides an expedient route to a series of tetracyclic carbazolothiophene compounds bearing the indole and thiophene rings. Among these samples, 9-benzyl-4-methyl-4-(4-hydroxyphenyl)-10-oxo-4,10-dih...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Babu G,Yu HM,Yang SM,Fang JM

    更新日期:2004-03-08 00:00:00

  • Thiophene-based vitronectin receptor antagonists.

    abstract::A series of alpha(v)beta(3) antagonists based on a thiophene scaffold were synthesized via two routes and evaluated for in vitro biological activity. We have identified several structurally similar antagonists with different selectivities towards alpha(IIb)beta(3), alpha(v)beta(5) and alpha(5)beta(1) at the cellular l...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Bubenik M,Meerovitch K,Bergeron F,Attardo G,Chan L

    更新日期:2003-02-10 00:00:00

  • Discovery of GSK143, a highly potent, selective and orally efficacious spleen tyrosine kinase inhibitor.

    abstract::The lead optimisation of the diaminopyrimidine carboxamide series of spleen tyrosine kinase inhibitors is described. The medicinal chemistry strategy was focused on optimising the human whole blood activity whilst achieving a sufficient margin over liability kinases and hERG activity. GSK143 is a potent and highly sel...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Liddle J,Atkinson FL,Barker MD,Carter PS,Curtis NR,Davis RP,Douault C,Dickson MC,Elwes D,Garton NS,Gray M,Hayhow TG,Hobbs CI,Jones E,Leach S,Leavens K,Lewis HD,McCleary S,Neu M,Patel VK,Preston AG,Ramirez-Molina

    更新日期:2011-10-15 00:00:00

  • Structure-based design of substituted biphenyl ethylene ethers as ligands binding in the hydrophobic pocket of gp41 and blocking the helical bundle formation.

    abstract::A series of substituted biphenyl ethylene ether compounds has been designed to target the gp41N-trimer in order to inhibit formation of the six-helical bundle that represents the end state of gp41-mediated viral fusion. A size exclusion HPLC based helical bundle formation (HBF) assay was developed to evaluate in vitro...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Liu B,Joseph RW,Dorsey BD,Schiksnis RA,Northrop K,Bukhtiyarova M,Springman EB

    更新日期:2009-10-01 00:00:00

  • Synthesis and anti-Candida activity of novel 2-hydrazino-1,3-thiazole derivatives.

    abstract::Eighteen new hydrazino-1,3-thiazole derivatives were evaluated against 8 strains of multi-resistant Candida spp. Introduction of an indolyl moiety linked to the hydrazone function enhanced the in vitro anti-Candida activity, with an activity spectrum towards Candida albicans strains. Introduction of a (S)-2-aminoethyl...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Maillard LT,Bertout S,Quinonéro O,Akalin G,Turan-Zitouni G,Fulcrand P,Demirci F,Martinez J,Masurier N

    更新日期:2013-03-15 00:00:00

  • Detection of NAD(P)H-dependent enzyme activity by time-domain ratiometry of terbium luminescence.

    abstract::NAD(P)H-dependent oxidoreductases play important roles in biology. Recently, we reported that the luminescence lifetime of some Tb(3+) complexes is sensitive to NAD(P)H, and we used this phenomenon to detect activities of these enzymes. However, conventional time-resolved luminescence assays are susceptible to static ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Terai T,Ito H,Hanaoka K,Komatsu T,Ueno T,Nagano T,Urano Y

    更新日期:2016-05-01 00:00:00

  • The role of phosphate in the action of thymidine phosphorylase inhibitors: Implications for the catalytic mechanism.

    abstract::The design and synthesis of 5-fluoro-6-[(2-aminoimidazol-1-yl)methyl]uracil (AIFU), a potent inhibitor of thymidine phosphorylase (TP) with K(i)-values of 11nM (ecTP) and 17nM (hTP), are described. Kinetic studies established that the type of inhibition of TP by AIFU is uncompetitive with respect to inorganic phosphat...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Jain HV,Rasheed R,Kalman TI

    更新日期:2010-03-01 00:00:00

  • Design, synthesis, and anticancer activities of novel perfluoroalkyltriazole-appended 2'-deoxyuridines.

    abstract::We have focused on the C5-modification of 2'-deoxyuridine with substituted heterocycles for bioactivity, such as antiviral or anticancer activity. Herein, we report a novel class of nucleoside analogues with perfluoroalkyltriazole moiety as an anticancer drug candidate. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Park SM,Yang H,Park SK,Kim HM,Kim BH

    更新日期:2010-10-01 00:00:00

  • Azabicyclic sulfonamides as potent 11beta-HSD1 inhibitors.

    abstract::Inhibition of 11beta-HSD1 has demonstrated potential in the treatment of various components of metabolic syndrome. We wish to report herein the discovery of novel azabicyclic sulfonamide based 11beta-HSD1 inhibitors. Highly potent compounds exhibiting inhibitory activities at both human and mouse 11beta-HSD1 were iden...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Shah U,Boyle CD,Chackalamannil S,Baker H,Kowalski T,Lee J,Terracina G,Zhang L

    更新日期:2010-03-01 00:00:00

  • Synthesis of enamino-2-oxindoles via conjugate addition between α-azido ketones and 3-alkenyl oxindoles: Cytotoxicity evaluation and apoptosis inducing studies.

    abstract::A facile method for the construction of double bond between 3-ylidene oxindoles and α-azido ketones has been successfully accomplished with a mild base. This method features azido reduction with concomitant double bond formation to provide the new class of bioactive enamino-2-oxindoles. These new compounds were screen...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Kumar NP,Vanjari Y,Thatikonda S,Pooladanda V,Sharma P,Sridhar B,Godugu C,Kamal A,Shankaraiah N

    更新日期:2018-12-01 00:00:00

  • Isotope edited NMR studies of glycosidases: design and synthesis of a novel glycosidase inhibitor.

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    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Hines JV,Chang H,Gerdeman MS,Warn DE

    更新日期:1999-05-03 00:00:00

  • Minimum structural requirements for cell membrane leakage-mediated anti-MRSA activity of macrocyclic bis(bibenzyl)s.

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    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Fujii K,Morita D,Onoda K,Kuroda T,Miyachi H

    更新日期:2016-05-01 00:00:00

  • Trifluoromethyl ketones as inhibitors of histone deacetylase.

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    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Frey RR,Wada CK,Garland RB,Curtin ML,Michaelides MR,Li J,Pease LJ,Glaser KB,Marcotte PA,Bouska JJ,Murphy SS,Davidsen SK

    更新日期:2002-12-02 00:00:00

  • 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: new high affinity ligands for the cannabinoid CB1 and CB2 receptors.

    abstract::Two series of 1-alkyl-2-aryl-4-(1-naphthoyl)pyrroles were synthesized and their affinities for the cannabinoid CB(1) and CB(2) receptors were determined. In the 2-phenyl series (5) the N-alkyl group was varied from n-propyl to n-heptyl. A second series of 23 1-pentyl-2-aryl-4-(1-naphthoyl)-pyrroles (6) was also prepar...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Huffman JW,Padgett LW,Isherwood ML,Wiley JL,Martin BR

    更新日期:2006-10-15 00:00:00

  • Effects of a novel carbocyclic analog of pyrrolo[2,3-d]pyrimidine nucleoside on pleiotropic induction of cell death in prostate cancer cells with different androgen responsiveness.

    abstract::Prostate cancer is the most frequently diagnosed cancer and is one of the leading causes of male cancer death in the world. Recently, in the course of our screening for a novel anticancer compound, we synthesized carbocyclic analogs of pyrrolo[2,3-d]pyrimidine nucleoside; compounds 5, and 6. In the current study, we r...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Suh H,Choi KW,Lee J,Ryou C,Rhee H,Lee CH

    更新日期:2016-02-15 00:00:00

  • 2-Arylimino-5,6-dihydro-4H-1,3-thiazines as a new class of cannabinoid receptor agonists. Part 3: Synthesis and activity of isosteric analogs.

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    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Kai H,Morioka Y,Koriyama Y,Okamoto K,Hasegawa Y,Hattori M,Koike K,Chiba H,Shinohara S,Iwamoto Y,Takahashi K,Tanimoto N

    更新日期:2008-12-15 00:00:00

  • DNA-templated click chemistry for creation of novel DNA binding molecules.

    abstract::We have developed a new methodology for producing new molecules that bind to dsDNA using DNA-templated click chemistry. The click reactions between the minor groove binding peptide and acridine intercalators were accelerated by the addition of dsDNA. Furthermore, the resulting peptide-acridine conjugate showed a sligh...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Imoto S,Hirohama T,Nagatsugi F

    更新日期:2008-10-15 00:00:00

  • Modulating the development of E. coli biofilms with 2-aminoimidazoles.

    abstract::The synthesis of a 20 member 2-aminoimidazole/triazole pilot library is reported. Each member of the library was screened for its ability to inhibit or promote biofilm development of either Escherichia coli and Acinetobacter baumannii. From this screen, E. coli-selective 2-aminoimidazoles were discovered, with the bes...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Reed CS,Huigens RW 3rd,Rogers SA,Melander C

    更新日期:2010-11-01 00:00:00

  • Absolute configurations of tubulin inhibitors taltobulin (HTI-286) and HTI-042 characterized by X-ray diffraction analysis and NMR studies.

    abstract::The stereochemistry of the tubulin inhibitors taltobulin HTI-286 (2) and HTI-042 (3) was determined by utilizing the DPFGSE 1D NOE experiment. Single crystal X-ray diffraction analysis further confirmed the absolute configuration of these two compounds, which carry the (S,S,S)-configuration necessary for biological ac...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Niu C,Ho DM,Williamson RT,Zask A,Ayral-Kaloustian S

    更新日期:2010-03-01 00:00:00

  • Synthesis and cytotoxic evaluation of novel ester-triazole-linked triterpenoid-AZT conjugates.

    abstract::Betulinic acid and analogous naturally occurring triterpenoid acids were transformed into the corresponding propargyl esters and subsequently deployed as substrates for a click chemistry-mediated coupling with azidothymidine (AZT) en route to novel 1,2,3-triazole-tethered triterpenoid-AZT conjugates. Twelve new hybrid...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Dang Thi TA,Kim Tuyet NT,Pham The C,Thanh Nguyen H,Ba Thi C,Doan Duy T,D'hooghe M,Van Nguyen T

    更新日期:2014-11-15 00:00:00

  • Crystal structures of human HSP90alpha-complexed with dihydroxyphenylpyrazoles.

    abstract::A series of dihydroxyphenylpyrazole compounds were identified as a unique class of reversible Hsp90 inhibitors. The crystal structures for two of the identified compounds complexed with the N-terminal ATP binding domain of human Hsp90alpha were determined. The dihydroxyphenyl ring of the compounds fits deeply into the...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Kreusch A,Han S,Brinker A,Zhou V,Choi HS,He Y,Lesley SA,Caldwell J,Gu XJ

    更新日期:2005-03-01 00:00:00

  • Learning from our mistakes: the 'unknown knowns' in fragment screening.

    abstract::In the past 15 years, fragment-based lead discovery (FBLD) has been adopted widely throughout academia and industry. The approach entails discovering very small molecular fragments and growing, merging, or linking them to produce drug leads. Because the affinities of the initial fragments are often low, detection meth...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Davis BJ,Erlanson DA

    更新日期:2013-05-15 00:00:00

  • N-alkyl-4-piperidinyl-2,3-diarylpyrrole derivatives with heterocyclic substitutions as potent and broad spectrum anticoccidial agents.

    abstract::Diaryl-(4-piperidinyl)-pyrrole derivatives bearing cyclic amine substituents have been synthesized and evaluated as anticoccidial agents. Improvements in potency of Et-PKG inhibition, such as azetidine derivative 3a, and broad spectrum anticoccidial activities in feed, such as morpholine derivative 8c, have been achie...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Liang GB,Qian X,Feng D,Fisher M,Crumley T,Darkin-Rattray SJ,Dulski PM,Gurnett A,Leavitt PS,Liberator PA,Misura AS,Samaras S,Tamas T,Schmatz DM,Wyvratt M,Biftu T

    更新日期:2008-03-15 00:00:00

  • Thiadiazole: a new family of intercalative photonuclease with electron transfer and radical mechanisms.

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    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Li Y,Xu Y,Qian X,Qu B

    更新日期:2003-10-20 00:00:00

  • Structure-activity relationship studies of a bisbenzimidazole-based, Zn(2+)-dependent inhibitor of HCV NS3 serine protease.

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    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Yeung KS,Meanwell NA,Qiu Z,Hernandez D,Zhang S,McPhee F,Weinheimer S,Clark JM,Janc JW

    更新日期:2001-09-03 00:00:00

  • Enhanced pneumocystis carinii activity of new primaquine analogues.

    abstract::New analogues of the venerable antimalarial drug primaquine have been synthesized and bioassayed in vivo against Pneumocystis carinii, a life-threatening infection common among immunosuppressed patients. Two of these new compounds are significantly more active than primaquine itself, and provide new information for fu...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Goodwin TE,Boylan CJ,Current WL,Byrd JC,Edwards CB,Fuller DA,Green JL,Larocca CD,Raney KD,Ross AS,Tucker WA

    更新日期:2000-10-02 00:00:00

  • Synthesis and structure-activity relationship of N-acyl-Gly-, N-acyl-Sar- and N-blocked-boroPro inhibitors of FAP, DPP4, and POP.

    abstract::The structure-activity relationship of various N-acyl-Gly-, N-acyl-Sar-, and N-blocked-boroPro derivatives against three prolyl peptidases was explored. Several N-acyl-Gly- and N-blocked-boroPro compounds showed low nanomolar inhibitory activity against fibroblast activation protein (FAP) and prolyl oligopeptidase (PO...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Tran T,Quan C,Edosada CY,Mayeda M,Wiesmann C,Sutherlin D,Wolf BB

    更新日期:2007-03-01 00:00:00