56428-57-0Relevant academic research and scientific papers
Synthesis and P2Y receptor activity of a series of uridine dinucleoside 5′-polyphosphates
Pendergast, William,Yerxa, Benjamin R.,Douglass III, James G,Shaver, Sammy R,Dougherty, Robert W.,Redick, Catherine C.,Sims, Ingrid F.,Rideout, Janet L.
, p. 157 - 160 (2001)
A series of dinucleoside 5-polyphosphates UpnU (n = 2-7) was synthesized. Their relative potencies as agonists at the G-protein-coupled receptors P2Y1, P2Y2, P2Y4, and P2Y6 were determined by intracellular calcium measurements using fluorescent imaging techniques. The correlation of phosphate chain length to activities at these receptors is discussed.
Synthesis of imidazole-activated ribonucleotides using cyanogen chloride
Yi, Ruiqin,Hongo, Yayoi,Fahrenbach, Albert C.
supporting information, p. 511 - 514 (2018/01/19)
We report the syntheses of ribonucleoside 5′-monophosphates activated with imidazole, using a mechanism which relies on the in situ generation of cyanogen chloride from the reaction of cyanide anion with hypochlorous acid. Cyanogen chloride reacts rapidly with imidazole to form diimidazole imine as the major product, a species which affords the activation of ribonucleoside 5′-monophosphates to their 5′-phosphorimidazolides.
SULFAMIDE LINKER, CONJUGATES THEREOF, AND METHODS OF PREPARATION
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, (2016/04/26)
The present invention relates to a compound comprising an alpha-end and an omega-end, the compound comprising on the alpha-end a reactive group Qlcapable of reacting with a functional group F1present on a biomolecule and on the omega-end a target molecule, the compound further comprising a group according to formula (1) or a salt thereof: Said compound may also be referred to as a linker-conjugate. The invention also relates to a process for the preparation of a bioconjugate, the process comprising the step of reacting a reactive group Q1of a linker-conjugate according to the invention with a functional group F1of a biomolecule. The invention further relates to a bioconjugate obtainable by the process according to the invention. In a preferred embodiment, the invention concerns a process for the preparation of a bioconjugate via a cycloaddition, such as a (4+2)-cycloaddition (e.g. a Diels-Alder reaction) or a (3+2)-cycloaddition (e.g. a 1,3-dipolar cycloaddition).
A Simple synthesis of sugar nucleoside diphosphates by chemical coupling in water
Tanaka, Hidenori,Yoshimura, Yayoi,Jürgensen, Malene R.,Cuesta-Seijo, Jose A.,Hindsgaul, Ole
supporting information, p. 11531 - 11534 (2013/01/15)
Sugar nucleotides made easy: The new reagent ImIm , which is formed in-situ in water, is shown to activate nucleoside 5'-phosphates to their imidazolides, these can subsequently couple with sugar-1-phosphates; the whole procedure takes place in water. This truly simple method yields a crude product mixture that can be used directly as a source of donors for glycosyltransferase- mediated oligsaccharide synthesis. In the scheme, B stands for the nucleobases U, A, or G. Copyright
Synthesis of nucleoside phosphosulfates
Kowalska, Joanna,Osowniak, Agnieszka,Zuberek, Joanna,Jemielity, Jacek
supporting information; experimental part, p. 3661 - 3664 (2012/07/27)
We describe an efficient and scalable procedure for the chemical synthesis of nucleoside 5′-phosphosulfates (NPS) from nucleoside 5′-phosphorimidazolides and sulfate bis(tributylammonium) salt. Using this method we obtained various NPS with yields ranging from 70-90%, including adenosine 5′-phosphosulfate (APS) and 2′,3′-cyclic precursor of 3′-phosphoadenosine 5′-phosphosulfate (PAPS), which are the key intermediates in the assimilation and metabolism of sulfur in all living organisms.
Reversible and efficient inhibition of UDP-galactopyranose mutase by electrophilic, constrained and unsaturated UDP-galactitol analogues
Ansiaux, Christophe,N'Go, Inès,Vincent, Stéphane P.
supporting information, p. 14860 - 14866 (2013/01/15)
A series of UDP-galactitols were designed as analogues of high-energy intermediates of the UDP-galactopyranose mutase (UGM) catalyzed furanose/pyranose interconversion, an essential step of Mycobacterium tuberculosis cell wall biosynthesis. The final compounds structurally share the UDP and the galactitol substructures that were connected by four distinct electrophilic connections (epoxide, lactone and Michael acceptors). All molecules were synthesized from a common perbenzylated acyclic galactose precursor that was derivatized by alkenylation, alkynylation and cyclopropanation. The inhibition study against UGM could clearly show that slight changes in the relative orientation of the UDP and the galactitol moieties resulted in dramatic variations of binding properties. Compared to known inhibitors, the epoxide derivative displayed a very tight, reversible, inhibition profile. Moreover, a time-dependent inactivation study showed that none of these electrophilic structures could react with UGM, or its FAD cofactor, the catalytic nucleophile of this still intriguing reaction. Shedding inhibitors: UDP-Galactopyranose mutase (UGM) is a validated target for treating tuberculosis. Its mechanism involves formation of a key covalent FAD-substrate intermediate, 1. A series of electrophilic UDP-galactitols were synthesized and assayed as inhibitors or inactivators of UGM. Strong inhibitions were observed, especially with epoxide 2. Interestingly, none of the molecules displayed an irreversible inhibition mode. Copyright
Convenient synthesis of nucleoside-5′-diphosphates from the corresponding ribonucleoside-5′-phosphoroimidazole
Kore, Anilkumar R.,Parmar, Gaurang
, p. 3393 - 3399 (2007/10/03)
The reaction of ribonucleoside-5′-phosphoroimidazolide with a tributylammonium orthophosphate in anhydrous dimethylformamide at room temperature provides a general method for the synthesis of nucleoside-5′- diphosphate. The novelty of the approach is to use the triethylammonium salt of 5′-monophosphate nucleoside derivative prior to the imidazolate reaction with imidazole, triphenylphosphine, and 2,2′-dithiodipyridine. Deprotection, followed by displacement of the imidazole moiety using tributylammonium orthophosphate and a catalytic amount of zinc chloride in dimethylformamide gave the desired 5′-diphosphate products. The triethyl ammonium salt of 5′-diphosphate nucleosides was purified by flash chromatography using DEAE (diethylaminoethyl weak anion exchange resin) Sepharosa fast flow packed in an XK 50/60 column on an Akta FPLC (Fast Protein Liquid Chromatography). Synthesis procedures are reported for adenosine-5′-diphosphate, uridine-5′-diphosphate, cytidine-5′-diphosphate, and guanosine-5′-diphosphate. Yields for the displacement reactions ranged from 95 to 97%. Thus, this method offers the advantages of shorter reaction time, greater product yield, and a more cost-effective synthetic route. Copyright Taylor & Francis Group, LLC.
Chemical synthesis of uridine 5′-diphospho-α-D-xylopyranose
Ishimizu, Takeshi,Uchida, Takashi,Sano, Kyoko,Hase, Sumihiro
, p. 309 - 311 (2007/10/03)
Uridine 5′-diphospho-α-d-xylopyranose, which donates d-xylose during glycoconjugate biosynthesis, was chemically synthesized from α-d-xylose 1-phosphate and uridine 5′-monophosphoimidazolide.
The first chemical synthesis of UDP[6-3H]-α-D- galactofuranose
Marino, Karina,Marino, Carla,Lima, Carlos,Baldoni, Luciana,De Lederkremer, Rosa M.
, p. 2958 - 2964 (2007/10/03)
Galactofuranose metabolism is a good target for the development of novel chemotherapeutic agents for the treatment of some microbial infections. This is a valid objective because galactofuranose is absent in mammals. Two enzymes are involved in the biosynthesis of molecules containing galactofuranose: a mutase, which catalyzes the interconversion of UDP-Galp and UDP-Galf, and D-galactofuranosyltransferases. The mechanism of action of the mutase and its inhibition is currently being investigated, whereas studies on the galactofuranosyltransferases have been hampered by the lack of a labeled galactofuranose nucleotide. In the present work we describe the chemical synthesis of UDP-α-D-[6-3H]Galf and we prove its effectiveness for incorporation of radioactive galactofuranose into a natural acceptor. This is the first report on the chemical synthesis of a labeled donor of galactofuranose with the potential for studying the galactofuranosyltransferases independently from the UDP-Galp mutase. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
Engineering human FHIT, a diadenosine triphosphate hydrolase, into an efficient dinucleoside polyphosphate synthase
Huang, Kaisheng,Frey, Perry A.
, p. 9548 - 9549 (2007/10/03)
The putative human tumor suppressor gene FHIT encodes Fhit, the fragile histidine triad protein. Fhit is thought to participate in a signal transduction pathway involving dinucleoside polyphosphates. Fhit catalyzes the Mg2+-dependent hydrolysis of P1-5′-O-adenosine-P3-5′-O-adenosine triphosphate (Ap3A) to AMP and MgADP. Mutation of His96 to glycine disables Fhit as a catalyst for the hydrolysis of phosphoanhydrides such as Ap3A. However, the mutated enzyme H96G-Fhit efficiently catalyzes the synthesis of phosphoanhydride bonds in reactions of nucleoside-5′-phosphimidazolides with nucleoside di- and triphosphates. H96G-Fhit can be employed in the synthesis of a wide range of dinucleoside tri- and tetraphosphates. We here describe the use of H96G-Fhit to catalyze the synthesis of Ap3A, Ap3C, Ap3G, Ap3T, Ap3U, Cp3U, Tp3U, dAp3U, Ap4A, Ap4U, and the fluorescent Ap4etheno-C. Copyright
