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化学

Regioselective O-Glycosylation Nucleosides 통해 는 임시 2', 3'-Diol 보호 Boronic 에스테 르에 의해이 당 Nucleosides의 합성에 대 한의

Published: July 26, 2018
doi:
10.3791/57897
, , ,
1製薬科学部,Tokyo University of Science, 2Imaging Frontier Center,Tokyo University of Science

概要

여기, 우리 제시이 당 nucleosides의 합성에 대 한 프로토콜을 통해 ribonucleosides의 regioselective Oglycosylation에 의해의 임시 보호 그들의 2′, 3′-diol moieties 주기적 boronic 에스테 르를 이용 하 여. 이 메서드는 아데노신, guanosine, cytidine, uridine, 5-methyluridine, 5-fluorouridine을 주고 해당이 당 nucleosides 등 여러 보호 nucleosides에 적용 됩니다.

Abstract

이 당 및 nucleobase moieties를 이루어져 있는 당 nucleosides 여러 bioactivities 데 천연 제품의 중요 한 그룹으로 알려져 왔다. Glycosyl 기증자와 수락자 같은 기판의 준비 지루한 보호 그룹 조작 및 정화에 필요한 화학 Oglycosylation 합성이 당 nucleosides를 일반적으로 유익한 전략 이지만, 각 합성 단계입니다. 한편, 여러 연구 단체는 boronic 보고 그리고 borinic 에스테 르는 보호 또는 탄수화물 유도체 regio-또는 stereoselective acylation, 알, silylation, glycosylation 달성 하기의 그룹을 활성화로 봉사. 이 문서에서는, boronic 산을 활용 하 여 보호 되지 않은 ribonucleosides의 regioselective Oglycosylation에 대 한 절차를 설명 합니다. 에스테 르 화 2 ‘, 3’-diol boronic 산 ribonucleosides의 게 p-toluenesulfenyl 존재 glycosyl 기증자와 diol, 그리고, 다음 Oglycosylation의 임시 보호 염화와 실버 triflate, 허가 줄이 당 nucleosides 5′-수 산 기 그룹의 regioselective 반응. 이 메서드는 guanosine, 아데노신, cytidine, uridine, 5-metyluridine, 5-fluorouridine 등 다양 한 nucleosides를 적용할 수 있습니다. 이 문서와 함께 제공 된 비디오 나타내고 보호 되지 않은 nucleosides의 Oglycosylation에 대 한 (시각적) 유용한 정보가 당 nucleosides, 뿐만 아니라 다양 한 생물학 관련의 합성에 대 한 그들의 아날로그 파생 상품입니다.

Introduction

nucleoside 탄수화물 moiety의 어원이 같은 말은이 당 nucleosides 연결 을 통해 O-glycosidic 본드, 자연스럽 게-발생 탄수화물 유도체1,2 의 귀중 한 클래스 구성 3,,45,,67. 예를 들어, 그들은 tRNA (전송 ribonucleic 산) 및 poly(ADP-ribose)와 같은 생물학 고분자에 통합 됩니다 (ADP 아데노신 diphosphate =), 뿐만 아니라 일부 항균 대리인 및 다른 생물학적 활성 물질 (예를 들어, adenophostins, amicetins, ezomycin)5,6,,89,10,11,12,13, 14,15,,1617,18,19. 따라서,이 당 nucleosides 및 그들의 유도체 약물 발견 연구에 대 한 리드 화합물을 것으로 예상 된다. 이 당 nucleosides의 합성에 대 한 방법론은 세 가지 범주로 분류 됩니다. 효소 O-glycosylation20,21, 화학 N-glycosylation5,9,,1622,23, 24, 그리고 화학 O-glycosylation7,9,14,16,18,,1924, 25,26,,2728,29,30,31,32,33, 34,35,,3637. 특히, 화학 Oglycosylation stereoselective 합성 및이 당 nucleosides의 대규모 합성에 대 한 효율적인 방법 것입니다. 이전 연구는 O-2′-deoxyribonucleoside 2 thioglycosyl 기증자 1, p-toluenesulfenyl 염화 물 및 triflate, 실버의 조합을 사용 하 여의 glycosylation 월급을 보여주었다는 원하는 당 nucleoside 3 (그림 1A; 아칸소 = aryl 및 PG = 보호 그룹)38.

이러한 결과 따라 우리는 ribonucleosides p-toluenesulfenyl 염화 물/실버 triflate 발기인 시스템 적용의 Oglycosylation를 개발 하기로 결정 했다. 동안 부분적으로 보호 된 ribonucleosides의 Oglycosylation의 몇 가지 예제 시연된7,9,,1416,18,19 ,,2432,33,34,35,36,37, 피임 또는 일시적으로 보호의 사용 ribonucleosides Oglycosylation 위한 glycosyl 수락자로 사소 하 게 보고 되었습니다. 따라서, 피임 또는 일시적으로 보호 된 ribonucleosides의 regioselective Oglycosylation의 개발 보호 하는 ribonucleosides의 그룹 조작 없이 더 도움이 합성 방법을 제공할 것 이다. Ribonucleosides의 regioselective Oglycosylation, 달성 하기 위하여 우리가에 초점을 맞춘 붕 소 화합물 때문에 regio-또는 stereoselective acylation, 알, silylation, 및 탄수화물의 glycosylation의 몇 가지 예 파생 상품의 도움으로 boronic 또는 borinic 산39,40,41,,4243,44,45 를 보고 ,4647,,4849,50. 이 문서에서는,이 당 nucleosides ribonucleosides 통해 boronic 에스테 르 중간의 5′-수 산 기 그룹에서 regioselective Oglycosylation 활용의 합성에 대 한 절차를 설명 합니다. 여기에 제시 된 전략, boronic 에스테 르 중간 6 boronic 산 5에서 regioselective Oglycosylation 수 있는 ribonucleoside 4 의 에스테 르 화에 의해 여유 것 이라고는 게이 당 nucleoside 8 (그림 1B)51thioglycosyl 기증자 7 으로 5′-수 산 기 그룹. 우리는 또한 핵 자기 공명 (NMR) 분광학, boronic 에스테 르의 형성을 관찰 하 여 ribonucleoside 및 boronic 산의 상호 작용을 공부 했다. 있도록 boronic 에스테 르 glycosylation 반응을 에스테 르 화 무수 조건을 glycosyl 기증자와 boronic 에스테 르의 가수분해를 방지 하기 위해 필요 합니다. 이 문서에서는, 연구자와 학생 화학 뿐만 아니라 다른 연구 분야에 대 한 성공적인 glycosylation 반응 무수 조건을 얻기 위해 일반적인 절차 설명 합니다.

Protocol

참고: 합성된 화합물의 모든 실험 데이터 [NMR, 적외선 spectroscopies (IR), 대량 spectroscopies (MS), 광학 회전 및 원소 분석 데이터] 이전 종이51에서 보고 되었다. 1. O-Glycosylation 반응에 대 한 절차 화합물 α/β-12 (표 1에 항목 12)의 합성참고: 항목 1-13 표 1 에 비슷한 절차를 사용 하 여 실행 되었다. 2′, 3′-diol ribonucle…

Representative Results

Uridine 10 thiomannoside α-9 Oglycosylation의 결과 표 160,61에서 요약 된다. 항목 1에서 O-glycosylation boronic 산 유도체의 부재에서 α-9 와 10 의 복잡 한 혼합물의 형성 귀착되는. 항목 2, 10 및 phenylboronic 산 11a 혼합 및 공동 pyridine와 1, 4-dioxan…

Discussion

이 논문의 목적은 당 nucleosides 지루한 보호 그룹 조작 없이 보호 ribonucleosides를 사용 하 여 준비 하는 편리한 합성 방법을 보여주는 것입니다. 우리는 여기 nucleosides 통해 는 임시 2′, 3′-diol 보호 주기적 boronic 에스테 르 (그림 1B)51의 regioselective Oglycosylations에 보고합니다.

주기적 boronic 에스테 르 중간의 준비는 중?…

開示

The authors have nothing to disclose.

Acknowledgements

이 연구에서 교육, 문화, 스포츠, 과학 및 기술 (MEXT) 일본의 연구비에 의해 융자 되었다 (화력 15 K 00408, 24659011, 24640156, 245900425 및 22390005 신 아오키에 대 한), 도쿄 생 화 확 적인 연구에서 교부 금에 의해 재단, 도쿄, 일본, 그리고 전략적 연구 분야에 대 한 상태 (도쿄 대학의 과학) 기금. 우리는 질량의 측정을 위한 Fukiko 하세가와 (약 학 교수, 도쿄 대학의 과학) NMR 스펙트럼의 측정을 위한 노리코 Sawabe (학부 약 학, 도쿄 대학의 과학)를 감사 하 고 싶습니다. 스펙트럼, 그리고 토모 코 마 츠 오 (도쿄 대학의 과학 기술과 과학 연구소) 원소 분석의 측정을 위한.

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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