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Chimie

Regioselective O- Glycosylation av nukleosider via den tillfälliga 2', 3'-Diol skydd av en Boronic Ester för syntesen av disackarid nukleosider

Published: July 26, 2018
doi:
10.3791/57897
, , ,
1Faculty of Pharmaceutical Sciences,Tokyo University of Science, 2Imaging Frontier Center,Tokyo University of Science

Summary

Här presenterar vi protokoll för syntesen av disackarid nukleosider av den regioselective O– glycosylation av ribonucleosides via en tillfälligt skydd av deras 2′, 3′-diol beståndsdelarna utnyttja en cyklisk boronic ester. Denna metod gäller flera oskyddade nukleosider som adenosin, guanosin, cytidin, uridin, 5-methyluridine och 5-fluorouridine att ge motsvarande disackarid nukleosider.

Abstract

Disackarid nukleosider, som består av disackarid och kvävebasen beståndsdelarna, har varit känd som en värdefull grupp av naturliga produkter med mångskiftande bioactivities. Även om kemiska O– glycosylation är en allmänt gynnsam strategi att syntetisera disackarid nukleosider, kräver beredning av substrat såsom glycosyl givare och acceptorer tråkiga skydda gruppen manipulationer och en rening på varje syntetisk steg. Samtidigt flera forskargrupper har rapporterat att boronic och borinic estrar fungera som en skyddande eller aktivera grupp av kolhydrat derivat för att uppnå den regio- eller stereoselektiv acylation alkylering, Silylering och glycosylation. I denna artikel visar vi förfarandet för den regioselective O– glycosylation av oskyddade ribonucleosides utnyttja boronic syra. Förestring av 2′, 3′-diol av ribonucleosides med boronic syra gör det tillfälliga skyddet av diol och, följande O– glycosylation med en glycosyl givare i närvaro av p– toluenesulfenyl klorid och silver triflate, tillstånd regioselective reaktionen av 5′-hydroxylgruppen råd de disackarid nukleosider. Denna metod skulle kunna tillämpas på olika nukleosider, såsom guanosin, adenosin, cytidin, uridin, 5-metyluridine och 5-fluorouridine. Denna artikel och den medföljande videon representerar användbar (visuell) information för den O– glycosylation av oskyddade nukleosider och deras analoger för syntesen av inte bara disackarid nukleosider, men också en mängd biologiskt relevanta derivat.

Introduction

Disackarid nukleosider, som konjugat av en nukleosid och en kolhydrat del länkas via en O-glycosidic bond, utgöra en värdefull klass av naturligt förekommande kolhydrater derivat1,2 ,3,4,5,6,7. Exempelvis de införlivas i biologiska makromolekyler som tRNA (överföring ribonukleinsyra) och poly(ADP-ribose) (ADP = adenosindifosfat), samt i vissa antibakteriella medel och andra biologiskt aktiva ämnen (t.ex. adenophostins, amicetins, ezomycin)5,6,8,9,10,11,12,13, 14,15,16,17,18,19. Disackarid nukleosider och deras derivat förväntas därför vara blyföreningar för upptäckten läkemedelsforskning. Metoderna för syntes av disackarid nukleosider klassificeras i tre kategorier; enzymatisk O– glycosylation20,21, kemiska N– glycosylation5,9,16,22,23, 24, och kemiska O– glycosylation7,9,14,16,18,19,24, 25,26,27,28,29,30,31,32,33, 34,35,36,37. I synnerhet skulle kemiska O– glycosylation vara en effektiv metod för stereoselektiv syntes och storskaliga syntes av disackarid nukleosider. Tidigare forskning har visat att de O– glycosylation 2′-deoxyribonucleoside 2 med thioglycosyl givare 1, med hjälp av kombination av p– toluenesulfenyl klorid och silver triflate, ger den önskas disackarid nukleosid 3 (figur 1A; Ar = aryl och PG = skydda gruppen)38.

Efter dessa resultat, bestämde vi oss att utveckla den O– glycosylation av ribonucleosides p– toluenesulfenyl klorid/silver triflate promotorn systemet. Medan flera exempel på den O– glycosylation av delvis skyddade ribonucleosides har varit visat7,9,14,16,18,19 ,24,32,33,34,35,36,37, användning av oskyddade eller tillfälligt-skyddade ribonucleosides som en glycosyl acceptor för O– glycosylation negligibly har rapporterats. Utvecklingen av regioselective O– glycosylation av oskyddade eller tillfälligt-skyddade ribonucleosides skulle därför ge ett mer fördelaktigt syntetisk metod utan att skydda gruppen manipulationer av ribonucleosides. För att uppnå den regioselective O– glycosylation av ribonucleosides, fokuserade vi på de boron föreningarna, eftersom flera exempel på regio- eller stereoselektiv acylation, alkylering, Silylering och glycosylation av kolhydrater derivat med hjälp av boronic eller borinic syra har varit rapporterade39,40,41,42,43,44,45 ,46,47,48,49,50. I denna artikel visar vi förfarandet för syntesen av disackarid nukleosider utnyttja regioselective O– glycosylation på 5′-hydroxylgruppen av ribonucleosides via en mellanliggande boronic ester. I strategin presenteras här, boronic ester mellanliggande 6 skulle ges av förestring av ribonucleoside 4 med boronic syra 5, som tillåter den regioselective O– glycosylation på den 5′-hydroxylgruppen med thioglycosyl givare 7 ge disackarid nukleosid 8 (figur 1B)51. Vi har också studerat samspelet mellan en ribonucleoside och boronic syra av kärnmagnetisk resonans (NMR) spektroskopi, att observera bildandet av en boronic ester. Förestring att göra en boronic ester och en glycosylation reaktion kräver vattenfri villkor för att förhindra hydrolys av boronic ester och glycosyl givare. I denna artikel visar vi de typiska förfarandena för att få de vattenfri villkor för framgångsrik glycosylation reaktioner för forskare och studenter inte bara i kemi, men också inom andra forskningsområden.

Protocol

Obs: Alla experimentella data [NMR, infraröd spektroskopier (IR), massa spektroskopier (MS), optiska rotationer och elementärt analyserar data] av de syntetiserade föreningarna har rapporterats i en tidigare papper51. 1. förfarandet för O- Glycosylation reaktioner Syntesen av sammansatta α/β-12 (post 12 i tabell 1)Obs: Posterna 1-13 i tabell 1 genomfördes med hjälp av ett liknande förfarande. <s…

Representative Results

Resultaten av den O- glycosylation av uridin 10 med thiomannoside α -9 sammanfattas i tabell 160,61. Posten 1 resulterade den O- glycosylation 10 med α -9 i avsaknad av boronic syra derivat i bildandet av en komplicerade blandning. I posten 2, 10 och phenylboronic syra 11a var blandade och samt…

Discussion

Syftet med detta manuskript är att visa en bekväm syntetisk metod för att förbereda disackarid nukleosider använder oskyddade ribonucleosides utan tråkiga skydda gruppen manipulationer. Här rapporterar vi om den regioselective O– Glykosyleringar av nukleosider via den tillfälliga 2′, 3′-diol skydd av en cyklisk boronic ester (figur 1B)51.

Utarbetandet av den cykliska boronic estern mellanliggande ?…

Divulgations

The authors have nothing to disclose.

Acknowledgements

Forskningen finansierades av grants-in-aid från ministeriet för utbildning, kultur, sport, vetenskap och teknik (MEXT) Japan (nr 15K 00408, 24659011, 24640156, 245900425 och 22390005 för Shin Aoki), av ett bidrag från Tokyo biokemiska forskningen Foundation, Tokyo, Japan, och av TUS (Tokyo University of Science) fonden för strategiska forskningsområden. Vi vill tacka Noriko Sawabe (farmaceutiska fakulteten, Tokyo University of Science) för mätningar av NMR spectrana, Fukiko Hasegawa (farmaceutiska fakulteten, Tokyo University of Science) för mätning av massan Spectra och Tomoko Matsuo (forskningsinstitut för vetenskap och teknik, Tokyo University of Science) för mätningar av de elementära analyserna.

Materials

Silver trifluoromethanesulfonate Nacalai Tesque 34945-61
Phenylboronic acid (contains varying amounts of anhydride) Tokyo Chemical Industry B0857
p-Methoxyphenylboronic acid Wako Pure Chemical Industries 321-69201
4-(Trifluoromethyl)phenylboronic acid (contains varying amounts of anhydride) Tokyo Chemical Industry T1788
2,4-Difluorophenylboronic acid (contains varying amounts of anhydride) Tokyo Chemical Industry D3391
Cyclopentylboronic acid (contains varying amounts of Anhydride) Tokyo Chemical Industry C2442
4-Nitrophenylboronic acid (contains varying amounts of anhydride) Tokyo Chemical Industry N0812
4-Hexylphenylboronic acid (contains varying amounts of anhydride) Tokyo Chemical Industry H1489
Adenosine Merck KGaA 862.
Guanosine Acros Organics 411130050
Cytidine Tokyo Chemical Industry C0522
Uridine Tokyo Chemical Industry U0020
5-Fluorouridine Tokyo Chemical Industry F0636
5-Methyluridine Sigma M-9885
Methylamine (40% in Methanol, ca. 9.8mol/L) Tokyo Chemical Industry M1016
N,N-dimethyl-4-aminopyridine Wako Pure Chemical Industries 044-19211
Acetic anhydride Nacalai Tesque 00226-15
Pyridine, Dehydrated Wako Pure Chemical Industries 161-18453
Acetonitrile Kanto Chemical 01031-96
1,4-Dioxane Nacalai Tesque 13622-73
Dichloromethane Wako Pure Chemical Industries 130-02457
Propionitrile Wako Pure Chemical Industries 164-04756
Molecular sieves 4A powder Nacalai Tesque 04168-65
Molecular sieves 3A powder Nacalai Tesque 04176-55
Celite 545RVS Nacalai Tesque 08034-85
Acetonitrile-D3 (D,99.8%) Cambridge Isotope Laboratories DLM-21-10
Trifluoroacetic acid Nacalai Tesque 34831-25
TLC Silica gel 60 F254 Merck KGaA 1.05715.0001
Chromatorex Fuji Silysia Chemical FL100D
Sodium hydrogen carbonate Wako Pure Chemical Industries 191-01305
Hydrochloric acid Wako Pure Chemical Industries 080-01061
Sodium sulfate Nacalai Tesque 31915-96
Chloroform Kanto Chemical 07278-81
Sodium chloride Wako Pure Chemical Industries 194-01677
Methanol Nacalai Tesque 21914-74
JEOL Always 300 JEOL Measurement of NMR
Lamda 400 JEOL Measurement of NMR
PerkinElmer Spectrum 100 FT-IR Spectrometer Perkin Elmer Measurement of IR
JEOL JMS-700 JEOL Measurement of MS
PerkinElmer CHN 2400 analyzer Perkin Elmer Measurement of elemental analysis
JASCO P-1030 digital polarimeter JASCO Measurement of optical rotation
JASCO PU-2089 Plus intelligent HPLC pump JASCO For HPLC
Jasco UV-2075 Plus Intelligent UV/Vis Detector JASCO For HPLC
Rheodyne Model 7125 Injector Sigma-Aldrich 58826 For HPLC
Chromatopac C-R8A Shimadzu For HPLC
Senshu Pak Pegasil ODS Senshu Scientific For HPLC
p-Toluenesulfenyl chloride Prepared  Ref. 38
Phenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-a-D-mannopyranoside (a-9) Prepared  Ref. 52
4-Metylphenyl 2,3,4,6-tetra-O-benzoyl-1-thio-b-D-galactopyranoside (b-21) Prepared  Ref. 53
4-Metylphenyl 2,3,4,6-tetra-O-benzoyl-1-thio-b-D-glucopyranoside (b-31) Prepared  Ref. 57
4-Metylphenyl 2,3,4,6-tetra-O-benzoyl-1-thio-a-D-Mannopyranoside (a-32) Prepared  Ref. 67
6-N-Benzoyladenosine (14) Prepared  Ref. 54
2-N-Isobutyrylguanosine (16) Prepared  Ref. 55
4-N-Benzoylcytidine (20) Prepared  Ref. 56
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Regioselective O-glycosylationNucleosideBoronic EsterDisaccharide NucleosideTemporary Diol ProtectionDrug DiscoveryGlycosylationUnprotected NucleosideReaction OptimizationSynthesis

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Someya, H., Itoh, T., Kato, M., Aoki, S. Regioselective O-Glycosylation of Nucleosides via the Temporary 2′,3′-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides. J. Vis. Exp. (137), e57897, doi:10.3791/57897 (2018).
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