Name: regioselective o-glycosylation of nucleosides via the temporary 2',3'-diol protection by a boronic ester for the synthesis of disaccharide nucleosides
Uploaded: 2018-07-26T13:00:00
Description: Watch this Scientific Journal Video about Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides at JoVE

Denne forskning er finansieret af grants-in-aid fra ministeriet for uddannelse, kultur, sport, videnskab og teknologi (MEXT) i Japan (nr. 15K 00408, 24659011, 24640156, 245900425 og 22390005 for Shin Aoki), af et tilskud fra Tokyo biokemiske forskning Foundation, Tokyo, Japan, og TUS (Tokyo University of Science) Fonden for strategiske forskningsområder. Vi vil gerne takke Noriko Sawabe (Farmaceutiske Fakultet, Tokyo University of Science) for målinger af NMR-spektre, Fukiko Hasegawa (Farmaceutiske Fakultet, Tokyo University of Science) for målinger af massen spektre, og Tomoko Matsuo (Research Institute for videnskab og teknologi, Tokyo University of Science) for målinger af de elementære analyser.

Bemærk: Alle eksperimentelle data [NMR, infrarød spectroscopies (IR), masse spectroscopies (MS), optisk rotationer og elementært analyser data] af de syntetiserede forbindelser blev rapporteret i en tidligere papir51.
1. proceduren for O- glykosylering reaktioner
<ol><li>Syntese af sammensatte α/β-12 (post 12 i tabel 1) Bemærk: Poster 1-13 i tabel 1 blev udført ved hjælp af en lignende procedure.<ol>
<li>
M...

Formålet med dette manuskript er at vise en praktisk syntetiske metode til at forberede disaccharid Nukleosider ved hjælp af ubeskyttet ribonucleosides uden kedelige at beskytte gruppe manipulationer. Vi rapporterer heri på regioselective O- glycosylations af Nukleosider via den midlertidige 2', 3'-diol beskyttelse af en cyklisk boronic ester (figur 1B)51.
Forberedelse af det cykliske boronic ester mell...

Disaccharid Nukleosider, som konjugater af en nucleoside og en kulhydrat gruppe forbundet via en O-glycosidic obligation, udgør en værdifuld klasse af naturligt forekommende kulhydrat derivater1,2 ,3,4,5,6,7. For eksempel, de er indarbejdet i biologiske makromolekyler såsom tRNA (transfer ribonukleinsyre) og poly(ADP-ribose) (ADP = adenosin ud), samt i nogle antibakterielle midler og andre biologisk aktive stoffer (f.eks. adenophostins, amicetins, ezomycin)5,6,8,9,10,11,12,13, 14,15,16,17,18,19. Dermed er disaccharid Nukleosider og deres derivater ventet at blive blyforbindelser for drug discovery forskning. Metoder til syntese af disaccharid Nukleosider inddeles i tre kategorier; enzymatisk O- glykosylering20,21, kemiske N- glykosylering5,9,16,22,23, 24, og kemiske O- glykosylering7,9,14,16,18,19,24, 25,26,27,28,29,30,31,32,33, 34,35,36,37. Især ville kemiske O- glykosylering være en effektiv metode til stereoselective syntese og omfattende syntese af disaccharid Nukleosider. Tidligere forskning har vist, at O- glykosylering af 2'-deoxyribonucleoside 2 med thioglycosyl donor 1, ved hjælp af en kombination af p- toluenesulfenyl chlorid og sølv triflate, giver de ønskes disaccharid nucleoside 3 (figur 1A; Ar = aryl og PG = beskytte gruppe)38.
Efter disse resultater besluttede vi at udvikle O- glykosylering af ribonucleosides anvende p- toluenesulfenyl chlorid/sølv triflate promotor system. Mens flere eksempler på O- glykosylering af delvist beskyttet ribonucleosides har været demonstreret7,9,14,16,18,19 ,24,32,33,34,35,36,37, udnyttelse af ubeskyttede eller midlertidigt beskyttet ribonucleosides som en glycosyl acceptor for O- glykosylering har rapporteret negligibly. Derfor, udvikling af regioselective O- glykosylering af ubeskyttede eller midlertidigt beskyttet ribonucleosides ville give et mere fordelagtigt syntetiske metode uden at beskytte gruppe manipulationer af ribonucleosides. For at opnå regioselective O- glykosylering af ribonucleosides, har vi fokuseret på borforbindelser, fordi flere eksempler på regio - og/eller stereoselective acylation, alkylering, silylering og glykosylering af kulhydrat derivater bistået af boronic eller borinic syre har været rapporteret39,40,41,42,43,44,45 ,46,47,48,49,50. I denne artikel viser vi proceduren for syntese af disaccharid Nukleosider udnytter regioselective O- glykosylering på 5'-hydroxyl gruppe af ribonucleosides via en boronic ester mellemliggende. I den strategi, der præsenteres her, ville boronic ester mellemliggende 6 gives ved forestring af ribonucleoside 4 med boronic syre 5, som giver mulighed for regioselective O- glykosylering på den 5'-hydroxyl gruppe med thioglycosyl donor 7 give disaccharid nucleoside 8 (figur 1B)51. Vi studerede også samspillet mellem en ribonucleoside og boronic syre af Kernemagnetisk resonans (NMR) spektroskopi, at observere dannelsen af en boronic ester. Esterificering at gøre en boronic ester og en glykosylering reaktion kræver vandfrie betingelser at forhindre hydrolyse af de boronic ester og glycosyl donor. I denne artikel viser vi de typiske procedurer for at opnå de vandfrie betingelser for vellykkede glykosylering reaktioner for forskere og studerende i kemi, men også i andre forskningsområder.

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			<td height="21" style="height:21px;width:241px;">Silver trifluoromethanesulfonate</td>
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			<td style="width:119px;">T1788</td>
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			<td height="63" style="height:63px;width:241px;">2,4-Difluorophenylboronic acid (contains varying amounts of anhydride)</td>
			<td style="width:255px;">Tokyo Chemical Industry</td>
			<td style="width:119px;">D3391</td>
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			<td style="width:119px;">C2442</td>
			<td></td>
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		<tr height="63">
			<td height="63" style="height:63px;width:241px;">4-Nitrophenylboronic acid (contains varying amounts of anhydride)</td>
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			<td></td>
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		<tr height="63">
			<td height="63" style="height:63px;width:241px;">4-Hexylphenylboronic acid (contains varying amounts of anhydride)</td>
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			<td style="width:255px;">Tokyo Chemical Industry</td>
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			<td></td>
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			<td height="21" style="height:21px;width:241px;">5-Fluorouridine</td>
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			<td height="21" style="height:21px;width:241px;">5-Methyluridine</td>
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			<td style="width:119px;">M-9885</td>
			<td></td>
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		<tr height="42">
			<td height="42" style="height:42px;width:241px;">Methylamine (40% in Methanol,&#160;ca. 9.8mol/L)</td>
			<td style="width:255px;">Tokyo Chemical Industry</td>
			<td style="width:119px;">M1016</td>
			<td></td>
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			<td style="width:119px;">044-19211</td>
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			<td style="width:119px;">01031-96</td>
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			<td></td>
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			<td style="width:255px;">Nacalai Tesque</td>
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			<td style="width:119px;">1.05715.0001</td>
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			<td style="width:255px;">Wako Pure Chemical Industries</td>
			<td style="width:119px;">191-01305</td>
			<td></td>
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			<td height="21" style="height:21px;width:241px;">Hydrochloric acid</td>
			<td style="width:255px;">Wako Pure Chemical Industries</td>
			<td style="width:119px;">080-01061</td>
			<td></td>
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			<td style="width:255px;">Nacalai Tesque</td>
			<td style="width:119px;">31915-96</td>
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			<td style="width:255px;">Kanto Chemical</td>
			<td style="width:119px;">07278-81</td>
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			<td>Measurement of NMR</td>
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			<td height="21" style="height:21px;width:241px;">Lamda 400</td>
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			<td style="width:119px;"></td>
			<td>Measurement of NMR</td>
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		<tr height="42">
			<td height="42" style="height:42px;width:241px;">PerkinElmer Spectrum 100 FT-IR Spectrometer</td>
			<td style="width:255px;">Perkin Elmer</td>
			<td style="width:119px;"></td>
			<td>Measurement of IR</td>
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		<tr height="21">
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			<td style="width:255px;">JEOL</td>
			<td style="width:119px;"></td>
			<td>Measurement of MS</td>
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		<tr height="21">
			<td height="21" style="height:21px;width:241px;">PerkinElmer CHN 2400 analyzer</td>
			<td style="width:255px;">Perkin Elmer</td>
			<td style="width:119px;"></td>
			<td>Measurement of elemental analysis</td>
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		<tr height="21">
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			<td style="width:255px;">JASCO</td>
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			<td>Measurement of optical rotation</td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:241px;">JASCO PU-2089 Plus intelligent HPLC pump</td>
			<td style="width:255px;">JASCO</td>
			<td style="width:119px;"></td>
			<td>For HPLC</td>
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		<tr height="42">
			<td height="42" style="height:42px;width:241px;">Jasco UV-2075 Plus Intelligent UV/Vis Detector</td>
			<td style="width:255px;">JASCO</td>
			<td style="width:119px;"></td>
			<td>For HPLC</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:241px;">Rheodyne Model 7125 Injector</td>
			<td style="width:255px;">Sigma-Aldrich</td>
			<td align="right" style="width:119px;">58826</td>
			<td>For HPLC</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:241px;">Chromatopac C-R8A</td>
			<td style="width:255px;">Shimadzu</td>
			<td style="width:119px;"></td>
			<td>For HPLC</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:241px;">Senshu Pak Pegasil ODS</td>
			<td style="width:255px;">Senshu Scientific</td>
			<td style="width:119px;"></td>
			<td>For HPLC</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:241px;">p-Toluenesulfenyl&#160;chloride</td>
			<td style="width:255px;"></td>
			<td style="width:119px;"></td>
			<td>Prepared&#160; Ref. 38</td>
		</tr>
		<tr height="60">
			<td height="60" style="height:60px;width:241px;">Phenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-a-D-mannopyranoside (a-9)</td>
			<td style="width:255px;"></td>
			<td style="width:119px;"></td>
			<td>Prepared&#160; Ref. 52</td>
		</tr>
		<tr height="63">
			<td height="63" style="height:63px;width:241px;">4-Metylphenyl 2,3,4,6-tetra-O-benzoyl-1-thio-b-D-galactopyranoside (b-21)</td>
			<td style="width:255px;"></td>
			<td style="width:119px;"></td>
			<td>Prepared&#160; Ref. 53</td>
		</tr>
		<tr height="63">
			<td height="63" style="height:63px;width:241px;">4-Metylphenyl 2,3,4,6-tetra-O-benzoyl-1-thio-b-D-glucopyranoside (b-31)</td>
			<td style="width:255px;"></td>
			<td style="width:119px;"></td>
			<td>Prepared&#160; Ref. 57</td>
		</tr>
		<tr height="63">
			<td height="63" style="height:63px;width:241px;">4-Metylphenyl 2,3,4,6-tetra-O-benzoyl-1-thio-a-D-Mannopyranoside (a-32)</td>
			<td style="width:255px;"></td>
			<td style="width:119px;"></td>
			<td>Prepared&#160; Ref. 67</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:241px;">6-N-Benzoyladenosine (14)</td>
			<td style="width:255px;"></td>
			<td style="width:119px;"></td>
			<td>Prepared&#160; Ref. 54</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:241px;">2-N-Isobutyrylguanosine (16)</td>
			<td style="width:255px;"></td>
			<td style="width:119px;"></td>
			<td>Prepared&#160; Ref. 55</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:241px;">4-N-Benzoylcytidine (20)</td>
			<td style="width:255px;"></td>
			<td style="width:119px;"></td>
			<td>Prepared&#160; Ref. 56</td>
		</tr>
	</tbody>
</table>

regioselective o-glycosylation of nucleosides via the temporary 2',3'-diol protection by a boronic ester for the synthesis of disaccharide nucleosides

Disaccharid Nukleosider, som består af disaccharid og nucleobase fraspaltning, har været kendt som en værdifuld gruppe af naturlige produkter med mangeartede bioactivities. Selv om kemiske O- glykosylering er et almindeligt gavnlige strategi at syntetisere disaccharid Nukleosider, kræver forberedelse af substrater såsom glycosyl donorer og acceptorer kedelige at beskytte gruppe manipulationer og en rensning på hver syntetiske trin. I mellemtiden, flere forskergrupper har rapporteret, at boronic og borinic estere tjener som en beskyttelse eller aktivering gruppe af kulhydrat derivater til at opnå regio - og/eller stereoselective acylation, alkylering, silylering og glykosylering. I denne artikel viser vi proceduren for regioselective O- glykosylering af ubeskyttet ribonucleosides udnytter boronic syre. Esterificering af 2', 3'-diol af ribonucleosides med boronic syre gør den midlertidige beskyttelse af diol og følgende O- glykosylering med en glycosyl donor i overværelse af p- toluenesulfenyl chlorid og sølv triflate, tilladelser regioselective reaktionen af 5'-hydroxyl gruppe råd til disaccharid Nukleosider. Denne metode kan anvendes til forskellige Nukleosider Guanosinmonofosfat, adenosin, cytidine, uridine, 5-metyluridine og 5-fluorouridine. Denne artikel og den ledsagende video repræsenterer nyttig (visuelle) information til O- glykosylering af ubeskyttede Nukleosider og deres analoger til syntese af ikke kun disaccharid Nukleosider, men også en bred vifte af biologisk relevante derivater.

Resultaterne af O- glykosylering af uridine 10 med thiomannoside α -9 er sammenfattet i tabel 160,61. I post 1 resulterede O- glykosylering af 10 med α -9 i mangel af boronic syre derivater i dannelsen af en kompliceret blanding. I post 2, 10 og phenylboronic syre 11a var blandet og co fordampe...

Watch this Scientific Journal Video about Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides at JoVE

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Her, vi præsenterer protokoller til syntese af disaccharid Nukleosider af regioselective O- glykosylering af ribonucleosides via en midlertidig beskyttelse af deres 2', 3'-diol fraspaltning udnytter en cyklisk boronic ester. Denne metode gælder for flere ubeskyttede Nukleosider adenosin, Guanosinmonofosfat, cytidine, uridine, 5-methyluridine og 5-fluorouridine til at give tilsvarende disaccharid Nukleosider.

Regioselective O- glykosylering af Nukleosider via den midlertidige 2', 3'-Diol beskyttelse af en Boronic Ester til syntese af disaccharid Nukleosider

Disaccharide nucleosides, which consist of disaccharide and nucleobase moieties, have been known as a valuable group of natural products having ...

Research

JoVE Journal

Chemistry

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Anticancer Metal Complexes: Synthesis and Cytotoxicity Evaluation by the MTT Assay

Anticancer metalkomplekser: Syntese og cytotoksicitet Evaluering af MTT Assay

Titanium (IV) and vanadium (V) complexes are highly potent anticancer agents. A challenge in their synthesis refers to their hydrolytic instability; ...

Formation of Ordered Biomolecular Structures by the Self-assembly of Short Peptides

Dannelse af Bestilte Biomolekylær Strukturer af Self-samling af korte peptider

In nature, complex functional structures are formed by the self-assembly of biomolecules under mild conditions. Understanding the forces that control ...

Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library

Split-og pool Syntese og karakterisering af peptid tertiær amid Library

Peptidomimetics are great sources of protein ligands. The oligomeric nature of these compounds enables us to access large synthetic libraries on solid ...

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

Syntese og oprensning af Iodoaziridines Inddragelse kvantitativ udvælgelse af det optimale stationære fase til kromatografi

The highly diastereoselective preparation of cis-N-Ts-iodoaziridines through reaction of diiodomethyllithium with N-Ts aldimines is described. ...

HKUST-1 as a Heterogeneous Catalyst for the Synthesis of Vanillin

HKUST-1 som en heterogen katalysator til syntese af vanillin

Vanillin (4-hydoxy-3-methoxybenzaldehyde) is the main component of the extract of vanilla bean. The natural vanilla scent is a mixture of approximately ...

Synthesis of Protein Bioconjugates via Cysteine-maleimide Chemistry

Synthesis of Protein Bioconjugates via Cysteine-maleimide Chemistry

Syntese af Protein biokonjugater<em&gt; via</em&gt; Cystein-maleimid Kemi

The chemical linking or bioconjugation of proteins to fluorescent dyes, drugs, polymers and other proteins has a broad range of applications, such as the ...

Facile Synthesis of Worm-like Micelles by Visible Light Mediated Dispersion Polymerization Using Photoredox Catalyst

Facile Syntese af ormelignende Miceller af synligt lys Mediated Dispersion polymerisering Brug Photoredox Catalyst

Presented herein is a protocol for the facile synthesis of worm-like micelles by visible light mediated dispersion polymerization. This approach begins ...

Hydroquinone Based Synthesis of Gold Nanorods

Hydroquinon Based Syntese af guld nanorods

Gold nanorods are an important kind of nanoparticles characterized by peculiar plasmonic properties. Despite their widespread use in nanotechnology, the ...

Protocol for the Solid-phase Synthesis of Oligomers of RNA Containing a 2'-O-thiophenylmethyl Modification and Characterization via Circular Dichroism

Protocol for the Solid-phase Synthesis of Oligomers of RNA Containing a 2'-O-thiophenylmethyl Modification and Characterization via Circular Dichroism

Protokol til fastfasesyntese af oligomerer af RNA indeholdende en 2&#39;-<em&gt; O</em&gt; -thiophenylmethyl-modifikation og karakterisering via cirkulær dikroisme

Solid-phase synthesis has been used to obtain canonical and modified polymers of nucleic acids, specifically of DNA or RNA, which has made it a popular ...

Synthesis of Substrate-Bound Au Nanowires Via an Active Surface Growth Mechanism

Syntese af substrat-bundet Au Nanowires Via en aktiv overflade vækst mekanisme

Advancing synthetic capabilities is important for the development of nanoscience and nanotechnology. The synthesis of nanowires has always been a ...