A novel solid support for synthesis of oligonucleotide 3'-phosphorothioate monoesters.

Abstract:

:A new reagent immobilized on solid support allowing for solid-phase synthesis of oligonucleotides with a 3'-terminal phosphorothioate monoester is described. The support is compatible with phosphoramidite chemistry for automated oligonucleotide synthesis. Final deprotection with ammonia under standard conditions leads to oligonucleotide 3'-terminal phosphorothioate.

journal_name

Bioorg Med Chem Lett

authors

Cheruvallath ZS,Cole DL,Ravikumar VT

doi

10.1016/s0960-894x(02)00922-8

subject

Has Abstract

pub_date

2003-01-20 00:00:00

pages

281-4

issue

2

eissn

0960-894X

issn

1464-3405

pii

S0960894X02009228

journal_volume

13

pub_type

杂志文章
  • Synthesis and evaluation of a cyclic imine derivative conjugated to a fluorescent molecule for labeling of proteins.

    abstract::A cyclic imine conjugated to a fluorescent dansyl group was synthesized and used for covalent labeling of proteins. The covalent attachment to proteins was confirmed by gel electrophoresis and mass analysis. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.12.071

    authors: Guo HM,Minakawa M,Ueno L,Tanaka F

    更新日期:2009-02-15 00:00:00

  • Synthesis and pharmacological evaluation of the stereoisomers of 3-carba cyclic-phosphatidic acid.

    abstract::Cyclic phosphatidic acid (CPA) is a naturally occurring analog of lysophosphatidic acid (LPA) in which the sn-2 hydroxy group forms a five-membered ring with the sn-3 phosphate. Here, we describe the synthesis of R-3-CCPA and S-3-CCPA along with their pharmacological properties as inhibitors of lysophospholipase D/aut...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.09.115

    authors: Gupte R,Siddam A,Lu Y,Li W,Fujiwara Y,Panupinthu N,Pham TC,Baker DL,Parrill AL,Gotoh M,Murakami-Murofushi K,Kobayashi S,Mills GB,Tigyi G,Miller DD

    更新日期:2010-12-15 00:00:00

  • Aptazyme-based riboswitches as label-free and detector-free sensors for cofactors.

    abstract::We constructed a label-free and detector-free aptazyme-based riboswitch sensor for detecting the cofactor of the aptazyme. This riboswitch, which usually suppresses the gene expression with its anti-RBS sequence bound to the RBS of its own mRNA (OFF), activates the translation only when a cofactor is added to release ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.03.033

    authors: Ogawa A,Maeda M

    更新日期:2007-06-01 00:00:00

  • Evaluation of HIV-1 inhibition by stereoisomers and analogues of the sesquiterpenoid hydroquinone peyssonol A.

    abstract::Peyssonol A, a brominated natural product with documented anti-HIV-1 activity, was synthesized racemically along with 6 isomers and 15 truncated analogues and synthetic precursors. These compounds were screened in a cell-based assay against a recombinant HIV-1 strain to investigate structure-activity relationships. Th...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.01.098

    authors: Treitler DS,Li Z,Krystal M,Meanwell NA,Snyder SA

    更新日期:2013-04-01 00:00:00

  • Potential CRF1R PET imaging agents: 1-fluoroalkylsubstituted 5-halo-3-(arylamino)pyrazin-2(1H)-ones.

    abstract::A series of pyrazinones were prepared and evaluated as potential CRF(1)R PET imaging agents. Optimization of their CRF(1)R binding potencies and octanol-phosphate buffer phase distribution coefficients are discussed herein. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.02.009

    authors: Denhart DJ,Zuev D,Ditta JL,Hartz RA,Ahuja VT,Mattson RJ,Huang H,Mattson GK,Zueva L,Nielsen JM,Kozlowski ES,Lodge NJ,Bronson JJ,Macor JE

    更新日期:2013-04-01 00:00:00

  • New polyphenols active on beta-amyloid aggregation.

    abstract::New polyphenol classes have been tested against amyloid-beta peptide aggregation. We have identified four novel polyphenols which could be efficient fibril inhibitors in Alzheimer's disease: malvidin and its glucoside and curculigosides B and D. We suggest that molecules with the particular C(6)-linkers-C(6) structure...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.11.028

    authors: Rivière C,Richard T,Vitrac X,Mérillon JM,Valls J,Monti JP

    更新日期:2008-01-15 00:00:00

  • 4-Aryl-2-anilinopyrimidines as corticotropin-releasing hormone (CRH) antagonists.

    abstract::A series of 4-aryl-2-(N-ethylanilino)pyrimidines has been synthesized as corticotropin-releasing hormone (CRH) inhibitors. The effect of substitution on each aromatic ring on receptor binding was investigated. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00132-8

    authors: Cocuzza AJ,Hobbs FW,Arnold CR,Chidester DR,Yarem JA,Culp S,Fitzgerald L,Gilligan PJ

    更新日期:1999-04-05 00:00:00

  • Syntheses of sphingosine-1-phosphate analogues and their interaction with EDG/S1P receptors.

    abstract::Sphingosine-1-phosphate (S1P) is an important regulator of a wide variety of biological processes acting as an endogenous ligand to EDG/S1P receptors. In an effort to establish structure-activity relationship between EDG/S1P and ligands, we report herein homology modeling study of EDG-1/S1P(1), syntheses of S1P analog...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.03.001

    authors: Lim HS,Park JJ,Ko K,Lee MH,Chung SK

    更新日期:2004-05-17 00:00:00

  • The insulin secretory action of novel polycyclic guanidines: discovery through open innovation phenotypic screening, and exploration of structure-activity relationships.

    abstract::We report the discovery of the glucose-dependent insulin secretogogue activity of a novel class of polycyclic guanidines through phenotypic screening as part of the Lilly Open Innovation Drug Discovery platform. Three compounds from the University of California, Irvine, 1-3, having the 3-arylhexahydropyrrolo[1,2-c]pyr...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.01.021

    authors: Shaghafi MB,Barrett DG,Willard FS,Overman LE

    更新日期:2014-02-15 00:00:00

  • Synthesis and antihormonal properties of novel 11β-benzoxazole-substituted steroids.

    abstract::Early studies led to the identification of 11β-aryl-4',5'-dihydrospiro[estra-4,9-diene-17β,4'-oxazole] analogs with potent and more selective antiprogestational activity compared to antiglucocorticoid activity than mifepristone. In the present study, we replaced the 4'-dimethylaminophenyl group of mifepristone with th...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.12.110

    authors: Jin C,Fix SE,Kepler JA,Cook CE

    更新日期:2012-02-15 00:00:00

  • 2-Arylimidazo[2,1-b]benzothiazoles: a new family of amyloid binding agents with potential for PET and SPECT imaging of Alzheimer's brain.

    abstract::We designed and synthesized a small series of 2-aryl-imidazo[2,1-b]benzothiazole, representing a combination of motifs from the two most potent amyloid imaging agents, PIB and IMPY. The binding affinity of the new compounds ranged from 6 to 133 nM. Among the best compounds, 3b (K(i)=6 nM) can be labeled with (11)CH(3)...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.03.052

    authors: Alagille D,DaCosta H,Baldwin RM,Tamagnan GD

    更新日期:2011-05-15 00:00:00

  • Opsin shift in an aldolase antibody.

    abstract::An antibody-retinal assembly that mimics the opsin shift (OS) of the naturally occurring visual pigments is reported. Both experiments and calculations show that the aldolase antibody 33F12 covalently binds all-trans retinal via a protonated Schiff base with a lysine residue. This chromophore, which exhibits a remarka...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00406-0

    authors: Grynszpan F,Keinan E

    更新日期:1999-08-16 00:00:00

  • Synthesis and immunological activity of an oligosaccharide-conjugate as a vaccine candidate against Group A Streptococcus.

    abstract::The synthesis and immunogenicity of a tetanus toxoid (TT)-conjugate of the hexasaccharide portion of the cell-wall polysaccharide (CWPS) of the Group A Streptococcus (GAS) is described. The synthesis relies on the reaction of an allyl glycoside of the hexasaccharide with cysteamine, followed by the reaction of the res...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.09.042

    authors: Auzanneau FI,Borrelli S,Pinto BM

    更新日期:2013-11-15 00:00:00

  • Multiple-step, one-pot synthesis of 2-substituted-3-phosphono-1-thia-4-aza-2-cyclohexene-5-carboxylates and their corresponding ethyl esters.

    abstract::The multiple-step, one-pot procedure for a series of 2-substituted-3-phosphono-1-thia-4-aza-2-cyclohexene-5-carboxylates, analogues of the natural, sulfur amino acid metabolite lanthionine ketimine (LK), its 5-ethyl ester (LKE) and 2-substituted LKEs is described. Initiating the synthesis with the Michaelis-Arbuzov pr...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2018.01.052

    authors: Shen D,Hensley K,Denton TT

    更新日期:2018-02-15 00:00:00

  • Syntheses of prodrug-type phosphotriester oligonucleotides responsive to intracellular reducing environment for improvement of cell membrane permeability and nuclease resistance.

    abstract::We synthesized prodrug-type phosphotriester (PTE) oligonucleotides containing the six-membered cyclic disulfide moiety by using phosphoramidite chemistry. Prodrug-type oligonucleotides named "Reducing-Environment-Dependent Uncatalyzed Chemical Transforming (REDUCT) PTE oligonucleotides" were converted into natural oli...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.05.031

    authors: Hayashi J,Samezawa Y,Ochi Y,Wada SI,Urata H

    更新日期:2017-07-15 00:00:00

  • Antifungal Sordarins. Part 4: synthesis and structure--activity relationships of 3',4'-fused alkyl-tetrahydrofuran derivatives.

    abstract::A series of Sordarin derivatives bearing alkyl substituted tetrahydrofuran rings fused to C3'-C4' bond of the sugar moiety have been prepared and their antifungal properties evaluated. Most of them show remarkable antifungal activity against Candida spp and Cryptococcus neoformans. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)00293-7

    authors: Bueno JM,Chicharro J,Fiandor JM,Gómez de las Heras F,Huss S

    更新日期:2002-07-08 00:00:00

  • Design and synthesis of a novel peptidomimetic inhibitor of HIV-1 Tat-TAR interactions: squaryldiamide as a new potential bioisostere of unsubstituted guanidine.

    abstract::By performing RNA-targeted structure-activity relationship studies, we discovered a novel peptidomimetic containing squaryldiamide as a potential bioisostere replacement for guanidine that binds transactivation responsive RNA with high affinity. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.06.077

    authors: Lee CW,Cao H,Ichiyama K,Rana TM

    更新日期:2005-10-01 00:00:00

  • Design, synthesis, and evaluation of oxyanion-hole selective inhibitor substituents for the S1 subsite of factor Xa.

    abstract::We have designed, synthesized, and evaluated the factor Xa inhibitory activities of p-amidinophenyl-sulfones, amines, and alcohols intended to take advantage of the polarity and hydrogen-bonding potential of the oxyanion hole region of the S1 specificity pocket. We demonstrate that placement of an anionic group within...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.07.054

    authors: Rumthao S,Lee O,Sheng Q,Fu W,Mulhearn DC,Crich D,Mesecar AD,Johnson ME

    更新日期:2004-10-18 00:00:00

  • Synthesis of Vorinostat and cholesterol conjugate to enhance the cancer cell uptake selectivity.

    abstract::Histone deacetylase (HDAC) inhibitors modulate various cellular functions including proliferation, differentiation, and apoptosis. Vorinostat (SuberAniloHydroxamic Acid, SAHA) is the first HDAC inhibitor approved by FDA for cancer treatment. However, SAHA distributes in cancer tissue and normal tissue in similar level...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.01.025

    authors: Idippily ND,Gan C,Orefice P,Peterson J,Su B

    更新日期:2017-02-15 00:00:00

  • Small-molecule microarrays: development of novel linkers and an efficient detection method for bound proteins.

    abstract::Novel isocyanate and diazoketone linkers possessing polyoxypropylenediamine as a spacer for small-molecule microrray are developed. White light interferometry is introduced to detect bound proteins on the glass slides without using chemically modified proteins. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.04.057

    authors: Kurosu M,Mowers WA

    更新日期:2006-07-01 00:00:00

  • Aromatic phosphonates inhibit the lysophospholipase D activity of autotaxin.

    abstract::Autotaxin (ATX) is an attractive target for the anticancer therapeutics that inhibits angiogenesis, invasion and migration. ATX is an extracellular lysophospholipase D that hydrolyzes lysophosphatidylcholine to form the bioactive lipid lysophosphatidic acid. The aromatic phosphonate S32826 was the first described nano...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.03.068

    authors: Jiang G,Madan D,Prestwich GD

    更新日期:2011-09-01 00:00:00

  • Synthesis, thermal stability, antimalarial activity of symmetrically and asymmetrically substituted tetraoxanes.

    abstract::Symmetrically and asymmetrically substituted 1,2,4,5-tetraoxanes were synthesized by the oxidative system H(2)O(2)/TFE in presence of MeReO(3) as a catalyst. All of the synthesized compounds were characterized spectroscopically, and evaluated for cytotoxicity, and antimalarial activity. Several of these tetraoxanes ex...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.12.069

    authors: Atheaya H,Khan SI,Mamgain R,Rawat DS

    更新日期:2008-02-15 00:00:00

  • InCl3 mediated one-pot multicomponent synthesis, anti-microbial, antioxidant and anticancer evaluation of 3-pyranyl indole derivatives.

    abstract::A simple and convenient method for the one-pot three-component synthesis of 3-pyranyl indoles has been accomplished by tandem Knoevenagel-Michael reaction of 3-cyanoacetyl indole, various aromatic aldehydes and malononitrile catalyzed by InCl(3) in ethanol under reflux conditions. The newly synthesized 3-pyranyl indol...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.07.039

    authors: Lakshmi NV,Thirumurugan P,Noorulla KM,Perumal PT

    更新日期:2010-09-01 00:00:00

  • Uridine phosphorylase inhibitors: chemical modification of benzyloxybenzyl-barbituric acid and its effects on urdpase inhibition.

    abstract::5-(o-Benzyloxy)benzylbarbituric acid (6) and 5-(p-benzyloxy)benzylbarbituric acid (7) were prepared and their inhibitory activities compared to 5-(m-benzyloxy)-benzylbarbituric acid (BBB) a known, potent inhibitor of uridine phosphorylase (UrdPase). Compounds 6 and 7 were 18-fold and 51-fold less active, respectively,...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00238-3

    authors: Guerin DJ,Mazeas D,Musale MS,Naguib FN,Al Safarjalani ON,el Kouni MH,Panzica RP

    更新日期:1999-06-07 00:00:00

  • Synthesis of hybrid acetogenins, alpha,beta-unsaturated-gamma-lactone-free nitrogen-containing heterocyclic analogues, and their cytotoxicity against human cancer cell lines.

    abstract::A series of alpha,beta-unsaturated-gamma-lactone-free nitrogen-containing heterocyclic analogues of solamin, a natural mono-THF acetogenin, have been synthesized and their cytotoxicity was investigated against 39 tumor cell lines. One of them, 1-methylpyrazol-5-yl derivative, showed selective increase of cytotoxicity ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.01.057

    authors: Kojima N,Fushimi T,Maezaki N,Tanaka T,Yamori T

    更新日期:2008-03-01 00:00:00

  • 4-arylphthalazin-1(2H)-one derivatives as potent antagonists of the melanin concentrating hormone receptor 1 (MCH-R1).

    abstract::A novel series of 4-arylphthalazin-1(2H)-one linked to arylpiperidines were synthesized and evaluated as MCH-R1 antagonists. The results of an extensive SAR study probing the effects of substituents on the 4-arylphthalazin-1(2H)-one C-4 aryl group led to the identification of the 4-(3,4-difluorophenyl) derivative as a...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.10.111

    authors: Lim CJ,Kim SH,Lee BH,Oh KS,Yi KY

    更新日期:2012-01-01 00:00:00

  • Identification of potent and selective VEGFR receptor tyrosine kinase inhibitors having new amide isostere headgroups.

    abstract::A novel series of malonamide-type dual VEGFR2/c-Met inhibitors in which one of the amide bonds was replaced by an amide isostere-a trifluoroethylamine unit, was designed, synthesized, and evaluated for their enzymatic and cellular inhibition of VEGFR2 and c-Met enzymes. Optimization of these molecular entities resulte...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.12.099

    authors: Gaudette F,Raeppel S,Nguyen H,Beaulieu N,Beaulieu C,Dupont I,Macleod AR,Besterman JM,Vaisburg A

    更新日期:2010-02-01 00:00:00

  • Synthetic studies and pharmacological evaluations on the MDMA ('Ecstasy') antagonist nantenine.

    abstract::The naturally occurring aporphine alkaloid nantenine, has been shown to antagonize behavioral and physiological effects of MDMA in mice. We have synthesized (+/-)-nantenine via an oxidative cyclization reaction with PIFA and evaluated its binding profile against a panel of CNS targets. To begin to understand the impor...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.11.053

    authors: Legendre O,Pecic S,Chaudhary S,Zimmerman SM,Fantegrossi WE,Harding WW

    更新日期:2010-01-15 00:00:00

  • Synthesis and biological evaluation of semi-synthetic albocycline analogs.

    abstract::Albocycline (ALB) is a unique macrolactone natural product with potent, narrow-spectrum activity against methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-intermediate (VISA), and vancomycin-resistant S. aureus (VRSA) strains (MIC = 0.5-1.0 μg/mL). Described herein is the synthesis and evaluation of a nov...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2020.127509

    authors: Daher SS,Franklin KP,Scherzi T,Dunman PM,Andrade RB

    更新日期:2020-11-01 00:00:00

  • 13C bis-labeled pyrroles: a tool for the identification of the rat metabolism of 3-methyl pyrrole-2,4-dicarboxylic acid 2-propyl ester 4-(1,2,2-trimethyl-propyl) ester.

    abstract::Following the recent disclosure of 3-methyl pyrrole-2,4-dicarboxylic acid 2-propyl ester 4-(1,2,2-trimethyl-propyl) ester as a potent and selective mGluR1 non-competitive antagonist, the use of a doubly (13)C-labeled analogue to identify, and consequently prevent, metabolically labile positions is reported. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.11.039

    authors: Micheli F,Cavanni P,Di Fabio R,Donati D,Hamdan M,Provera S,Tranquillini ME,Vitulli G

    更新日期:2007-02-15 00:00:00