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Chimie

Regioselective O- glykosylering av Nucleosides via den midlertidige 2', 3-Diol beskyttelse av en Boronic Ester for syntese av smakløst Nucleosides

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

Summary

Her presenterer vi protokoller for syntese av smakløst nucleosides av regioselective O– glykosylering av ribonucleosides via en midlertidig beskyttelse av deres 2, 3-diol moieties utnytte en syklisk boronic ester. Denne metoden gjelder flere ubeskyttet nucleosides som adenosin, guanosine, cytidine, uridine, 5-methyluridine og 5-fluorouridine å gi tilsvarende smakløst nucleosides.

Abstract

Smakløst nucleosides, som består av smakløst og nucleobase moieties, har vært kjent som en verdifull gruppe av naturlige produkter har mangfoldige bioactivities. Selv om kjemisk O– glykosylering er en vanligvis nyttig strategi å syntetisere smakløst nucleosides, krever utarbeidelse av underlag som glycosyl givere og acceptors langtekkelig beskytte gruppe manipulasjoner og en renselse på hvert syntetiske trinn. I mellomtiden flere forskningsgrupper har rapportert at boronic og borinic estere tjene som en beskytter eller aktivere gruppe karbohydrater derivater for å oppnå den regio – og/eller stereoselektiv acylation, alkylation, silylation og glykosylering. I denne artikkelen viser vi prosedyren for regioselective O– glykosylering av ubeskyttet ribonucleosides utnytte boronic syre. Esterification av 2, 3-diol av ribonucleosides med boronic syre gjør midlertidig beskyttelse av diol, og følgende O– glykosylering med glycosyl giver i nærvær av p– toluenesulfenyl chloride og sølv triflate, tillater regioselective reaksjon gruppen 5′-hydroksyl råd smakløst nucleosides. Denne metoden kan brukes til ulike nucleosides, som guanosine, adenosin, cytidine, uridine, 5-metyluridine og 5-fluorouridine. Denne artikkelen og på videoen representerer nyttig (visuell) informasjon for O– glykosylering av ubeskyttet nucleosides og deres analogs for syntese av ikke bare smakløst nucleosides, men også en rekke biologisk relevante derivater.

Introduction

Smakløst nucleosides, som er conjugates av en nukleosid og en karbohydratholdige moiety koblet via en O-glycosidic bånd, utgjør en verdifull klasse av naturlig forekommende karbohydrater derivater1,2 ,3,4,5,6,7. For eksempel, de innlemmes i biologiske makromolekyler som tRNA (overføring ribonukleinsyre) og poly(ADP-ribose) (ADP = adenosindifosfat), så vel som i noen 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. Derfor er smakløst nucleosides og deres derivater forventet å være føre forbindelser for drug discovery forskning. Metodikkene for syntese av smakløst nucleosides klassifiseres i tre kategorier; enzymatisk O– glykosylering20,21, kjemiske N– glykosylering5,9,16,22,23, 24, og kjemiske O– glykosylering7,9,14,16,18,19,24, 25,26,27,28,29,30,31,32,33, 34,35,36,37. Spesielt ville kjemiske O– glykosylering være effektiv metode for stereoselektiv syntese og store syntese av smakløst nucleosides. Tidligere undersøkelser har vist at O– glykosylering av 2-deoxyribonucleoside 2 med thioglycosyl donor 1, med kombinasjonen av p– toluenesulfenyl chloride og sølv triflate, gir den ønsket smakløst nukleosid 3 (figur 1A; AR = aryl og PG = beskytte grupper)38.

Disse resultatene vi besluttet å utvikle O– glykosylering av ribonucleosides bruker p– toluenesulfenyl chloride/sølv triflate promoter systemet. Mens flere eksempler på O– glykosylering av delvis beskyttet ribonucleosides har vært demonstrert7,9,14,16,18,19 ,24,32,33,34,35,36,37, bruk av ubeskyttet eller midlertidig-beskyttet ribonucleosides som en glycosyl godkjenner for O– glykosylering er rapportert negligibly. Derfor vil utviklingen av regioselective O– glykosylering av ubeskyttet eller midlertidig-beskyttet ribonucleosides gi en mer gunstig syntetiske metode uten å beskytte gruppe manipulering av ribonucleosides. For å oppnå regioselective O– glykosylering av ribonucleosides, fokuserte vi på boron forbindelser, fordi flere eksempler på regio – og/eller stereoselektiv acylation, alkylation, silylation og glykosylering karbohydrater derivater assistert av boronic eller borinic syre har vært rapportert39,40,41,42,43,44,45 ,46,47,48,49,50. I denne artikkelen viser vi prosedyren for syntese av smakløst nucleosides utnytte regioselective O– glykosylering på 5′-hydroksyl gruppe på ribonucleosides via en boronic ester mellomliggende. I strategien presenteres her, ville boronic ester mellomliggende 6 gis av esterification av ribonucleoside 4 med boronic syre 5, som lar regioselective O– glykosylering på den 5′-hydroksyl gruppe med thioglycosyl donor 7 å gi smakløst nukleosid 8 (figur 1B)51. Vi har også studert samhandlingen mellom en ribonucleoside og boronic syre av kjernefysiske magnetisk resonans (NRM) spektroskopi, å observere dannelsen av en boronic ester. Esterification å gjøre en boronic ester og en glykosylering reaksjon krever vannfri forhold å hindre hydrolyse av boronic ester og glycosyl donor. I denne artikkelen viser vi typisk prosedyrene for å få vannfri betingelsene for vellykket glykosylering reaksjoner for forskere og studenter ikke bare i kjemi, men også i andre forskningsfelt.

Protocol

Merk: Alle eksperimentelle data [NMR, infrarøde spectroscopies (IR), masse spectroscopies (MS), optisk rotasjoner og elementær analyser data] av syntetisk forbindelsene ble rapportert i et tidligere papir51. 1. prosedyre for O- glykosylering reaksjoner Syntese av sammensatte α/β-12 (oppføring 12 i tabell 1)Merk: 1-13-oppføringer i tabell 1 ble gjennomført med omtrent. Midlertidig beskyttels…

Representative Results

Resultatene av O- glykosylering uridine 10 med thiomannoside α -9 oppsummeres i tabell 160,61. I oppføringen 1 resultert O- glykosylering 10 med α -9 i fravær av boronic acid derivater i dannelsen av en komplisert blanding. I post 2, 10 og phenylboronic syre 11a ble blandet co fordampet med p…

Discussion

Hensikten med denne oppgaven er å vise en praktisk syntetiske metode å forberede smakløst nucleosides bruke ubeskyttet ribonucleosides uten kjedelig beskytte gruppe manipulasjoner. Vi rapporterer her på regioselective O– glycosylations av nucleosides via den midlertidige 2′, 3-diol beskyttelse av en syklisk boronic ester (figur 1B)51.

Utarbeidelse av syklisk boronic ester mellomliggende er en av de vik…

Divulgations

The authors have nothing to disclose.

Acknowledgements

Denne forskningen ble finansiert av grants-in-aid fra Kunnskapsdepartementet, kultur, sport, vitenskap og teknologi (MEXT) i Japan (nr. 15K 00408, 24659011, 24640156, 245900425 og 22390005 for Shin Aoki), av en bevilgning fra Tokyo biokjemiske forskning Foundation, Tokyo, Japan, og av TUS (Tokyo University of Science) fondet for strategisk forskningsområder. Vi vil gjerne takke Noriko Sawabe (fakultetet av farmasøytiske Sciences, Tokyo University of Science) for målinger av NMR spekter, Fukiko Hasegawa (fakultetet av farmasøytiske Sciences, Tokyo University of Science) for målinger av massen Spectra og Tomoko Matsuo (Research Institute for vitenskap og teknologi, Tokyo University of Science) for målinger av elementær analysene.

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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