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Chimie

苷 2 ', 3 ' -二醇酯对双糖苷合成的选择性O-糖基化

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

Summary

在这里, 我们提出了合成双糖苷的协议, 选择性O-糖基化的 ribonucleosides通过临时保护其 2 ‘, 3 ‘-二醇的基团利用循环硼酸酯。该方法适用于几种不受保护的苷, 如腺苷、鸟嘌呤、胞苷、苷、5-methyluridine 和 5-fluorouridine, 给予相应的双糖苷。

Abstract

由双糖和碱基基团组成的双糖苷被称为具有多种生物活性的有价值的天然产物。虽然化学O-糖基化是一种普遍有益的战略, 以合成双糖苷, 制备基质如糖捐赠者和受体需要繁琐的保护组操作和净化每个合成步骤。同时, 一些研究小组报告说, 硼酸和 borinic 酯作为一种保护或活化的碳水化合物衍生物, 以实现立体酰化、烷基化、硅烷化和糖基性。本文介绍了利用硼酸对无保护 ribonucleosides 进行选择性邻糖基化的过程。以硼酸为 ribonucleosides 的 2 ‘, 3 ‘-二醇的酯化, 使二醇的临时保护, 并在 toluenesulfenyl 氯和银三氟存在后, 与糖的捐助者进行邻糖基化, 允许5 ‘-羟基的选择性反应, 以支付双糖苷。该方法可应用于各种苷, 如鸟嘌呤、腺苷、胞苷、苷、5-metyluridine 和 5-fluorouridine。这篇文章和随附的视频代表了有用的 (视觉) 信息的O-糖基化的无保护苷及其类似物的合成不仅双糖苷, 而且还有各种生物相关衍生物。

Introduction

双糖苷, 是核苷的共轭物和通过 O型糖苷键连接的碳水化合物基团, 构成了一类自然发生的碳水化合物衍生物1,2 ,3,4,5,6,7。例如, 它们被纳入生物大分子, 如 tRNA (转移核糖核酸) 和聚 (adp-核糖) (adp = 磷酸腺苷), 以及一些抗菌剂和其他生物活性物质 (例如,adenophostins, amicetins, ezomycin)5,6,8,9,10,11,12,13, 14,15,16,17,18,19。因此, 双糖苷及其衍生物有望成为药物发现研究的铅化合物。双糖苷的合成方法分为三类;酶法O-糖基化20,21, 化学n-糖基化5,9,16,22,23, 24、化学O-糖基化7、9、14、16、18、19、24、 25,26,27,28,29,30,31,32,33, 34,35,36,37。化学O-糖基化是一种有效的立体合成和双糖苷的大规模合成方法。以往的研究表明, 2 ‘-deoxyribonucleoside 2与 thioglycosyl 捐助者1的O糖基化, 采用 toluenesulfenyl 氯和银三氟的结合, 提供了理想的双糖核苷3 (图 1A;Ar = 芳和 PG = 保护组)38。

根据这些结果, 我们决定应用 toluenesulfenyl 氯化/银三氟启动子系统, 开发 ribonucleosides 的邻糖基化。虽然部分保护 ribonucleosides 的O-糖基化的几个例子已经证明了 7,9,14,16,18,19 、24、32、33、34、35、36、37、使用无保护或暂时保护ribonucleosides 作为糖受体的O-糖基化已微乎其微报道。因此, 不受保护的或暂时保护的 ribonucleosides 的选择性O-糖基化的发展将提供一种更有益的合成方法, 而不需要对 ribonucleosides 的群操作进行防护。为了实现 ribonucleosides 的选择性O-糖基化, 我们重点研究了硼化合物, 因为几个例子的内和/或立体酰化, 烷基, 硅烷化和糖基性的碳水化合物39,40,41,42,43,44,45 , 被硼酸或 borinic 酸辅助的衍生物报告了,46,47,48,49,50。在本文中, 我们展示了通过硼酸酯中间体在 ribonucleosides 的 5 ‘-羟基双糖苷中利用选择性邻糖基化合成的方法。在这里提出的战略, 硼酸酯中间体6将提供的酯化的 ribonucleoside 4与硼酸5, 这使得选择性O-糖基化在5 ‘-羟基基团与 thioglycosyl 捐赠者7给双糖核苷8 (图 1B)51。通过核磁共振 (NMR) 光谱学研究了 ribonucleoside 和硼酸的相互作用, 观察了硼酸酯的形成。酯化使硼酸酯和糖基化反应要求无水条件, 以防止硼酸酯和糖的水解。在这篇文章中, 我们展示了为研究人员和学生不仅在化学, 而且在其他研究领域获得成功的糖基化反应提供无水条件的典型程序。

Protocol

注: 所有实验数据 [核磁共振, 红外线 spectroscopies (IR), 质量 spectroscopies (MS), 光学旋转, 和元素分析数据] 的合成化合物被报告在前51篇。 1. O-糖基化反应的程序 复方α/β-12 的合成 (表1中的进入 12)注:表 1中的条目 1-13 是使用类似的程序进行的。 2 ‘, 3 ‘-二醇 ribonucleoside40的临时保护 …

Representative Results

在表 160,61中总结了苷10与 thiomannoside α-9的邻糖基化的结果。在进入 1, O-糖基化10与α-9在没有硼酸衍生物导致形成一个复杂混合物。进入 2, 10和苯硼酸11a混合, 并与吡啶和14二恶烷共蒸发, 然后, 在其回流温度下, 在14二恶烷中搅?…

Discussion

本手稿的目的是展示一个方便的合成方法, 以制备双糖苷使用无保护的 ribonucleosides, 而不繁琐的保护组操作。我们在此报告的选择性O-glycosylations 的苷通过临时 2 ‘, 3 ‘-二醇保护的循环硼酸酯 (图 1B)51。

循环硼酸酯中间体的制备是其中的重要步骤之一。无水溶剂应用于反应混合物的共同蒸发 (步骤1.1.1.2 和 1.2. 1.1….

Divulgations

The authors have nothing to disclose.

Acknowledgements

这项研究由日本教育、文化、体育、科学和技术部 (下个15K00408、24659011、24640156、245900425和22390005号为新青木) 提供的助学金资助, 由东京生物化学研究资助。基金会, 东京, 日本, 和由土族 (东京科学大学) 基金的战略研究领域。我们要感谢纪子 Sawabe (东京理工大学药科学院) 测量核磁共振谱, 璐子长谷川 (美国东京理工大学药学系) 为质量的测量光谱和友子松 (东京理工大学科技研究院) 对元素分析的测量。

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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References

  1. Kobayashi, J., Doi, Y., Ishibashi, M. Shimofuridin A, a nucleoside derivative embracing an acylfucopyranoside unit isolated from the okinawan marine tunicate Aplidium multiplicatum. The Journal of Organic Chemistry. 59, 255-257 (1994).
  2. Takahashi, M., Tanzawa, K., Takahashi, S. Adenophostins, newly discovered metabolites of penicillium brevicompactum, act as potent agonists of the inositol 1,4,5-trisphosphate receptor. The Journal of Biological Chemistry. 269, 369-372 (1994).
  3. Haneda, K. Cytosaminomycins, new anticoccidial agents produced by Strevtomvces sp. KO-8119 I. taxonomy, production, isolation and physico-chemical and biological properties. The Journal of Antibiotics. 47, 774-781 (1994).
  4. Shiomi, K., Haneda, K., Tomoda, H., Iwai, Y., Omura, S. Cytosaminomycins, new anticoccidial agents produced by Streptomyces sp. KO-8119 II. structure elucidation of cytosaminomycins A, B, C and D. The Journal of Antibiotics. 47, 782-786 (1994).
  5. Knapp, S. Synthesis of complex nucleoside antibiotics. Chemical Reviews. 95, 1859-1876 (1995).
  6. Efimtseva, E. V., Kulikova, I. V., Mikhailov, S. N. Disaccharide nucleosides as an important group of natural compounds. Journal of Molecular Biology. 43, 301-312 (2009).
  7. Huang, R. M., et al. Marine nucleosides: Structure, bioactivity, synthesis and biosynthesis. Marine Drugs. 12, 5817-5838 (2014).
  8. Efimtseva, E. V., Mikhailov, S. N. Disaccharide nucleosides and oligonucleotides on their basis. New tools for the study of enzymes of nucleic acid metabolism. Biochemistry (Moscow). 67, 1136-1144 (2002).
  9. Mikhailov, S. N., Efimtseva, E. V. Disaccharide nucleosides. Russian Chemical Reviews. 73, 401-414 (2004).
  10. Kimura, K., Bugg, T. D. H. Recent advances in antimicrobial nucleoside antibiotics targeting cell wall biosynthesis. Natural Product Reports. 20, 252-273 (2003).
  11. Winn, M., Goss, R. J. M., Kimura, K., Bugg, T. D. H. Antimicrobial nucleoside antibiotics targeting cell wall assembly: Recent advances in structure-function studies and nucleoside biosynthesis. Natural Product Reports. 27, 279-304 (2010).
  12. Takahashi, M., Kagasaki, T., Hosoya, T., Takahashi, S. Adenophostins A and B: Potent agonists of inositol-1,4,5-trisphosphate receptor produced by Penicillium brevicompactum. Taxonomy, fermentation, isolation, physico-chemical and biological properties. The Journal of Antibiotics. 46, 1643-1647 (1993).
  13. Takahashi, S., Kinoshita, T., Takahashi, M. Adenophostins A and B: Potent agonists of inositol-1,4,5-trisphosphate receptor produced by penicillium brevicompactum. Structure elucidation. The Journal of Antibiotics. 47, 95-100 (1994).
  14. Hotoda, H., Takahashi, M., Tanzawa, K., Takahashi, S., Kaneko, M. IP3 receptor-ligand. 1: Synthesis of adenophostin A. Tetrahedron Letters. 36, 5037-5040 (1995).
  15. Hirota, J., et al. Adenophostin-medicated quantal Ca2+ release in the purified and reconstituted inositol 1,4,5-trisphosphate receptor type 1. FEBS Letters. 368, 248-252 (1995).
  16. McCormick, J., et al. Structure and total synthesis of HF-7, a neuroactive glyconucleoside disulfate from the funnel-web spider Hololena curta. Journal of the American Chemical Society. 121, 5661-5665 (1999).
  17. Bu, Y. Y., Yamazaki, H., Ukai, K., Namikoshi, M. Anti-mycobacterial nucleoside antibiotics from a marine-derived Streptomyces sp. TPU1236A. Marine Drugs. 12, 6102-6112 (2014).
  18. Knapp, S., Gore, V. K. Synthesis of the ezomycin nucleoside disaccharide. Organic Letters. 2, 1391-1393 (2000).
  19. Behr, J. B., Gourlain, T., Helimi, A., Guillerm, G. Design, synthesis and biological evaluation of hetaryl-nucleoside derivatives as inhibitors of chitin synthase. Bioorganic & Medicinal Chemistry Letters. 13, 1713-1716 (2003).
  20. Binder, W. H., Kӓhlig, H., Schmid, W. Galactosylation by use of β-galactosidase: Enzymatic syntheses of disaccharide nucleosides. Tetrahedron: Asymmetry. 6, 1703-1710 (1995).
  21. Ye, M., Yan, L. -. Q., Li, N., Zong, M. -. H. Facile and regioselective enzymatic 5-galactosylation of pyrimidine 2-deoxynucleosides catalyzed by β-glycosidase from bovine liver. Journal of Molecular Catalysis B: Enzymatic. 79, 35-40 (2012).
  22. Niedballa, U., Vorbrüggen, H. A general synthesis of N-glycosides. III. Simple synthesis of pyrimidine disaccharide nucleosides. The Journal of Organic Chemistry. 39, 3664-3667 (1974).
  23. Abe, H., Shuto, S., Matsuda, A. Synthesis of the C-glycosidic analog of adenophostin A, a potent IP3 receptor agonist, using a temporary silicon-tethered radical coupling reaction as the key step. Tetrahedron Letters. 41, 2391-2394 (2000).
  24. Watanabe, K. A., et al. Nucleosides. 114. 5′-O-Glucuronides of 5-fluorouridine and 5-fluorocytidine. Masked precursors of anticancer nucleosides. Journal of Medicinal Chemistry. 24, 893-897 (1981).
  25. Khan, S. H., O’Neill, R. A. . Modern Methods in Carbohydrate Synthesis. , (1996).
  26. Lindhorst, T. K. . Essentials ofCarbohydrate Chemistry and Biochemistry. , (2007).
  27. Demchenko, A. V. . Handbook of Chemical Glycosylation. , (2008).
  28. Chen, X., Halcomb, R. L., Wang, P. G. Chemical Glycobiology (ACS Symposium Series 990). American Chemical Society. , (2008).
  29. Toshima, K., Tatsuta, K. Recent progress in O-glycosylation methods and its application to natural products synthesis. Chemical Reviews. 93, 1503-1531 (1993).
  30. Ito, Y. My stroll in the backyard of carbohydrate chemistry. Trends in Glycoscience and Glycotechnology. 22, 119-140 (2010).
  31. Yasomanee, J. P., Demchenko, A. V. From stereocontrolled glycosylation to expeditious oligosaccharide synthesis. Trends in Glycoscience and Glycotechnology. 25, 13-41 (2013).
  32. Nakamura, M., Fujita, S., Ogura, H. Synthesis of disaccharide nucleoside derivatives of 3-deoxy-ᴅ-glycero-ᴅ-galacto-2-nonulosonic acid (KDN). Chemical and Pharmaceutical Bulletin. 41, 21-25 (1993).
  33. Mikhailov, S. N., et al. Studies on disaccharide nucleoside synthesis. Mechanism of the formation of trisaccharide purine nucleosides. Nucleosides & Nucleotides. 18, 691-692 (1999).
  34. Lichtenthaler, F. W., Sanemitsu, Y., Nohara, T. Synthesis of 5′-O-glycosyl-ribo-nucleosides. Angewandte Chemie International Edition. 17, 772-774 (1978).
  35. Knapp, S., Gore, V. K. Synthesis of the shimofuridin nucleoside disaccharide. The Journal of Organic Chemistry. 61, 6744-6747 (1996).
  36. Zhang, Y., Knapp, S. Glycosylation of nucleosides. The Journal of Organic Chemistry. 81, 2228-2242 (2016).
  37. Xing, L., Niu, Q., Li, C. Practical glucosylations and mannosylations using anomeric benzoyloxy as a leaving group activated by sulfonium ion. ACS Omega. 2, 3698-3709 (2017).
  38. Aoki, S., et al. Synthesis of disaccharide nucleosides by the O-glycosylation of natural nucleosides with thioglycoside donors. Chemistry – An Asian Journal. 10, 740-751 (2015).
  39. Duggan, P. J., Tyndall, E. M. Boron acids as protective agents and catalysts in synthesis. Journal of the Chemical Society, Perkin Transactions 1. , 1325-1339 (2002).
  40. Yamada, K., Hayakawa, H., Wada, T. Method for preparation of 2′-O-alkylribonucleosides by regioselective alkylation of 2′,3′-O-(arylboronylidene) ribonucleosides. JPN. Patent. 5, (2009).
  41. Lee, D., Taylor, M. S. Borinic acid-catalyzed regioselective acylation of carbohydrate derivatives. Journal of the American Chemical Society. 133, 3724-3727 (2011).
  42. Gouliaras, C., Lee, D., Chan, L., Taylor, M. S. Regioselective activation of glycosyl acceptors by a diarylborinic acid-derived catalyst. Journal of the American Chemical Society. 133, 13926-13929 (2011).
  43. Satoh, H., Manabe, S. Design of chemical glycosyl donors: Does changing ring conformation influence selectivity/reactivity. Chemical Society Reviews. 42, 4297-4309 (2013).
  44. Liu, X., et al. 1,2-trans-1-Dihydroxyboryl benzyl S-glycoside as glycosyl donor. Carbohydrate Research. 398, 45-49 (2014).
  45. Kaji, E., et al. Thermodynamically controlled regioselective glycosylation of fully unprotected sugars through bis(boronate) intermediates. European Journal of Organic Chemistry. , 3536-3539 (2014).
  46. Nakagawa, A., Tanaka, M., Hanamura, S., Takahashi, D., Toshima, K. Regioselective and 1,2-cis-α-stereoselective glycosylation utilizing glycosyl-acceptor-derived boronic ester catalyst. Angewandte Chemie International Edition. 127, 11085-11089 (2015).
  47. Tanaka, M., Nashida, J., Takahashi, D., Toshima, K. Glycosyl-acceptor-derived borinic ester-promoted direct and β-stereoselective mannosylation with a 1,2-anhydromannose donor. Organic Letters. 18, 2288-2291 (2016).
  48. Nishi, N., Nashida, J., Kaji, E., Takahashi, D., Toshima, K. Regio- and stereoselective β-mannosylation using a boronic acid catalyst and its application in the synthesis of a tetrasaccharide repeating unit of lipopolysaccharide derived from E. Coli O75. Chemical Communications. 53, 3018-3021 (2017).
  49. Mancini, R. S., Leea, J. B., Taylor, M. S. Boronic esters as protective groups in carbohydrate chemistry: Processes for acylation, silylation and alkylation of glycoside-derived boronates. Organic & Biomolecular Chemistry. 15, 132-143 (2017).
  50. Mancini, R. S., Lee, J. B., Taylor, M. S. Sequential functionalizations of carbohydrates enabled by boronic esters as switchable protective/activating groups. The Journal of Organic Chemistry. 82, 8777-8791 (2017).
  51. Someya, H., Itoh, T., Aoki, S. Synthesis of disaccharide nucleosides utilizing the temporary protection of the 2′,3′-cis-diol of ribonucleosides by a boronic ester. Molecules. 22, 1650 (2017).
  52. Lemanski, G., Ziegler, T. Synthesis of 4-O-ᴅ-mannopyranosyl-α-ᴅ-glucopyranosides by intramolecular glycosylation of 6-O-tethered mannosyl donors. Tetrahedron. 56, 563-579 (2000).
  53. Liu, G., Zhang, X., Xing, G. A general method for N-glycosylation of nucleobases promoted by (p-Tol)2SO/Tf2O with thioglycoside as donor. Chemical Communications. 51, 12803-12806 (2015).
  54. Zhu, X. -. F., Williams, H. J., Scott, A. I. An improved transient method for the synthesis of N-benzoylated nucleosides. Synthetic Communications. 33, 1233-1243 (2003).
  55. Eisenführ, A., et al. A ribozyme with michaelase activity: Synthesis of the substrate precursors. Bioorganic & Medicinal Chemistry. 11, 235-249 (2003).
  56. Samuels, E. R., McNary, J., Aguilar, M., Awad, A. M. Effective synthesis of 3′-deoxy-3′-azido nucleosides for antiviral and antisense ribonucleic guanidine (RNG) applications. Nucleosides, Nucleotides and Nucleic Acids. 32, 109-123 (2013).
  57. France, R. R., Rees, N. V., Wadhawan, J. D., Fairbanks, A. J., Compton, R. G. Selective activation of glycosyl donors utilising electrochemical techniques: a study of the thermodynamic oxidation potentials of a range of chalcoglycosides. Organic & Biomolecular Chemistry. 2, 2188-2194 (2004).
  58. Wunderlich, C. H., et al. Synthesis of (6-13C)pyrimidine nucleotides as spin-labels for RNA dynamics. Journal of the American Chemical Society. 134, 7558-7569 (2012).
  59. Abraham, R. C., et al. Conjugates of COL-1 monoclonal antibody and β-ᴅ-galactosidase can specifically kill tumor cells by generation of 5-fluorouridine from the prodrug β-ᴅ-galactosyl-5-fluorouridine. Cellular Biophysics. 24, 127-133 (1994).
  60. Huang, X., Huang, L., Wang, H., Ye, X. -. S. Iterative one-pot synthesis of oligosaccharides. Angewandte Chemie International Edition. 43, 5221-5224 (2004).
  61. Verma, V. P., Wang, C. -. C. Highly stereoselective glycosyl-chloride-mediated synthesis of 2-deoxyglucosides. Chemistry – A European Journal. 19, 846-851 (2013).
  62. Martínez-Aguirre, M. A., Villamil-Ramos, R., Guerrero-Alvarez, J. A., Yatsimirsky, A. K. Substituent effects and pH profiles for stability constants of arylboronic acid diol esters. The Journal of Organic Chemistry. 78, 4674-4684 (2013).
  63. Wulff, G., Röhle, G. Results and problems of O-glycoside synthesis. Angewandte Chemie International Edition. 13, 157-170 (1974).
  64. Demchenko, A., Stauch, T., Boons, G. -. J. Solvent and other effects on the stereoselectivity of thioglycoside glycosidations. Synlett. , 818-820 (1997).
  65. Welch, C. J., Bazin, H., Heikkilä, J., Chattopadhyaya, J. Synthesis of C-5 and N-3 arenesulfenyl uridines. Preparation and properties of a new class of uracil protecting group. Acta Chemica Scandinavica. 39, 203-212 (1985).
  66. Tam, P. -. H., Lowary, T. L. Synthesis of deoxy and methoxy analogs of octyl α-ᴅ-mannopyranosyl-(1→6)-α-ᴅ-mannopyranoside as probes for mycobacterial lipoarabinomannan biosynthesis. Carbohydrate Research. 342, 1741-1772 (2007).
  67. Yalpani, M., Boeseb, R. The structure of amine adducts of triorganylboroxines. Chemische Berichte. 116, 3347-3358 (1983).
  68. McKinley, N. F., O’Shea, D. F. Efficient synthesis of aryl vinyl ethers exploiting 2,4,6-trivinylcyclotriboroxane as a vinylboronic acid equivalent. The Journal of Organic Chemistry. 69, 5087-5092 (2004).
  69. Iovine, P. M., Fletcher, M. N., Lin, S. Condensation of arylboroxine structures on Lewis basic copolymers as a noncovalent strategy toward polymer functionalization. Macromolecules. 39, 6324-6326 (2006).
  70. Chen, T. -. B., Huzak, M., Macura, S., Vuk-Pavlović, S. Somatostatin analogue octreotide modulates metabolism and effects of 5-fluorouracil and 5-fluorouridine in human colon cancer spheroids. Cancer Letters. 86, 41-51 (1994).
  71. Agudo, R., et al. Molecular characterization of a dual inhibitory and mutagenic activity of 5-fluorouridine triphosphate on viral RNA synthesis. Implications for lethal mutagenesis. Journal of Molecular Biology. 382, 652-666 (2008).
  72. Kirienko, D. R., Revtovich, A. V., Kirienko, N. V. A high-content, phenotypic screen identifies fluorouridine as an inhibitor of pyoverdine biosynthesis and Pseudomonas aeruginosa virulence. mSphere. 1, 00217 (2016).
  73. Wu, Q., Xia, A., Lin, X. Synthesis of monosaccharide derivatives and polymeric prodrugs of 5-fluorouridine via two-step enzymatic or chemo-enzymatic highly regioselective strategy. Journal of Molecular Catalysis B: Enzymatic. 54, 76-82 (2008).
  74. Brusa, P., et al. In vitro and in vivo antitumor activity of immunoconjugates prepared by linking 5-fluorouridine to antiadenocarcinoma monoclonal antibody. Il Farmaco. 52, 71-81 (1997).
  75. Ozaki, S., et al. 5-Fluorouracil derivatives XX.: Synthesis and antitumor activity of 5′-O.-unsaturated acyl-5-fluorouridines. Chemical and Pharmaceutical Bulletin. 38, 3164-3166 (1990).
  76. Martino, M. M., Jolimaitre, P., Martino, R. The prodrugs of 5-fluorouracil. Current Medicinal Chemistry. Anti-Cancer Agents. 2, 267-310 (2002).

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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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