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Química

Regioselective O- glikozilasyon nükleozitler üzerinden geçici 2', 3'-Diol koruması tarafından Boronic Ester Disaccharide nükleozitler sentezi için

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

Summary

Burada, bir geçici koruma ribonucleosides ile regioselective O– glikozilasyon tarafından iletişim kuralları disaccharide nükleozitler sentezi için mevcut onların 2′, döngüsel bir boronic ester kullanan 3′-diol moieties. Bu yöntem Adenozin, guanozin sitidin Üridin 5-methyluridine ve ilgili disaccharide nükleozitler vermek 5-fluorouridine gibi birkaç korumasız nükleozitler uygulanır.

Abstract

Moieties disaccharide ve nükleobazından oluşur, disaccharide nükleozitler doğal ürünler çok yönlü bioactivities sahip değerli bir grup olarak bilinmektedir. Kimyasal O– glikozilasyon disaccharide nükleozitler sentezlemek için yaygın olarak yararlı bir strateji olsa da, glikosil bağış ve alıcısı gibi yüzeylerde hazırlanması sıkıcı koruma grubu manipülasyonlar ve bir saflaştırma gerektirir Sentetik her adım. Bu arada, birkaç araştırma grubu bu boronic bildirdin ve borinic esterleri bir koruma veya aktive regio – ve/veya stereoselective asilasyonu, alkillenme, silylation ve glikozilasyon ulaşmak için karbonhidrat türevleri grup olarak hizmet vermektedir. Bu makalede, biz regioselective O– glikozilasyon, korumasız ribonucleosides boronic asit kullanan yordamı göstermek. Esterleşme, 2′ 3′-diol ribonucleosides boronic asit ile geçici koruma diol ve aşağıdaki O– glikozilasyon glikosil donör huzurunda p– toluenesulfenyl klorür ve gümüş triflate, izni yapar regioselective tepki disaccharide nükleozitler göze 5′-hidroksil grubunun. Bu yöntem guanozin, adenozin sitidin Üridin 5-metyluridine ve 5-fluorouridine gibi çeşitli nükleozitler için uygulanabilir. Bu makale ve beraberindeki video korumasız nükleozit, O– Glikozilasyon için yararlı (görsel) bilgi ve kendi analogları disaccharide nükleozitler, hem de biyolojik olarak ilgili çeşitli sentezi için temsil eder türevleri.

Introduction

Conjugates bir nükleozit ve karbonhidrat yan vardır disaccharide nükleozitler bağlı yolu ile bir O-glycosidic bağ, doğal olarak meydana gelen karbonhidrat türevleri1,2 değerli bir sınıf teşkil ,3,4,5,6,7. Örneğin, tRNA (transfer ribonükleik asit) ve poly(ADP-ribose) biyolojik oluştururlar içinde dahil edilmiştir (ADP adenozin nükleotittir =), yanı sıra bazı antibakteriyel ajanları ve diğer biyolojik olarak aktif maddeler (Örneğin, adenophostins, amicetins, ezomycin)5,6,8,9,10,11,12,13, 14,15,16,17,18,19. Bu nedenle, disaccharide nükleozitler ve onların türevleri ilaç bulma araştırma için kurşun bileşikleri olması bekleniyor. Metodolojisi disaccharide nükleozitler sentezi için üç kategoride sınıflandırılır; enzimatik O– glikozilasyon20,21, kimyasal N– glikozilasyon5,9,16,22,23, 24ve kimyasal O– glikozilasyon7,9,14,16,18,19,24, 25,26,27,28,29,30,31,32,33, 34,35,36,37. Özellikle, kimyasal O– glikozilasyon stereoselective sentezi ve disaccharide nükleozitler büyük ölçekli sentezi için verimli bir yöntem olacaktır. Önceki araştırma O– glikozilasyon 2′-deoxyribonucleoside 2 thioglycosyl donör 1 p– toluenesulfenyl klorür ve gümüş triflate, bileşimini kullanarak, affords göstermiştir istenen disaccharide nükleozit 3 (resim 1A; AR aril ve PG = koruma grubu =)38.

Bu sonuçlar O– glikozilasyon ribonucleosides p– toluenesulfenyl klorür/gümüş triflate organizatörü sistemi uygulayarak, geliştirmeye karar verdi. Ise O– glikozilasyon kısmen korunmuş ribonucleosides, çeşitli örnekler gösterdi7,9,14,16,18,olabilirdi19 ,24,32,33,34,35,36,37, korumasız veya geçici olarak korunan kullanımı ribonucleosides O– Glikozilasyon için glikosil alıcısı olarak negligibly bildirilmiştir. Bu nedenle, regioselective O– glikozilasyon, korumasız veya geçici olarak korunan ribonucleosides gelişimi ribonucleosides grubu işlemler koruma olmadan daha faydalı bir sentetik yöntemi sağlar. Regioselective O– glikozilasyon ribonucleosides, elde etmek için biz üzerinde bor bileşikleri, çünkü odaklı regio – ve/veya stereoselective asilasyonu, alkillenme, silylation ve karbonhidrat glikozilasyon çeşitli örnekler türevleri destekli tarafından boronic veya borinic asit-si olmak be39,40,41,42,43,44,45 bildirdi ,46,47,48,49,50. Bu makalede, biz regioselective O– glikozilasyon ribonucleosides yolu ile boronic ester ara 5′-hidroksil grubu, kullanan disaccharide nükleozitler sentezi için yordamı göstermek. Burada sunulan stratejisinde boronic ester ara 6 ribonucleoside 4 , regioselective O– glikozilasyon sağlayan boronic asit ile 5, esterleşme tarafından tanınan disaccharide nükleozit 8 (Şekil 1B)51vermek 5′-hidroksil grubuyla thioglycosyl donör 7 . Ayrıca boronic ester oluşumu gözlemlemek için nükleer manyetik rezonans (NMR) spektroskopisi tarafından ribonucleoside ve boronic asit etkileşimi okudu. Boronic ester ve glikozilasyon tepki yapmak esterleşme boronic ester ve glikosil donör hidroliz önlemek için susuz koşulları gerektirir. Bu makalede, araştırmacılar ve öğrenciler Kimya hem de diğer araştırma alanlarında başarılı glikozilasyon reaksiyonlar için susuz koşulları elde etmek için tipik yordamlar gösterir.

Protocol

Not: Bir önceki kağıt51de tüm deneysel veriler [NMR, kızılötesi spectroscopies (IR), kitle spectroscopies (MS), optik rotasyonlar ve elemental analizler veri] sentezlenen bileşiklerin bildirildi. 1. O- glikozilasyon reaksiyonlar için yordamı Bileşik α/β-12 (Tablo 1’deki giriş 12) senteziNot: Tablo 1 1-13 girişlerinde benzer bir yordam kullanılarak yapılmıştır. 2′, 3′-diol ribon…

Representative Results

O- glikozilasyon Üridin 10 thiomannoside α -9 ile sonuçları Tablo 160,61′ özetlenir. 1. giriş, O- glikozilasyon 10 α -9 yokluğunda boronic asit türevleri, karmaşık bir karışımı oluşumunda sonuçlandı. Giriş 2’de, 10 phenylboronic asit 11a karışık ve pyridine ve 1,4-dioxane il…

Discussion

Bu yazının amacı sıkıcı koruma grubunun manipülasyon olmadan korunmasız ribonucleosides kullanarak disaccharide nükleozitler hazırlamak için uygun bir sentetik Yöntem göstermektir. Biz burada regioselective O– glycosylations, nükleozit ile geçici 2′, 3′-diol koruma çevrimsel boronic ester (Şekil 1B)51tarafından rapor.

Çevrimsel boronic ester ara hazırlanması önemli adımlardan biridir…

Declarações

The authors have nothing to disclose.

Acknowledgements

Bu araştırma grants-in-aid Milli Eğitim Bakanlığı, kültür, spor, bilim ve teknoloji (MEXT) Japonya dan tarafından finanse edildi (NOS 15K 00408, 24659011, 24640156, 245900425 ve 22390005 Shin Aoki için), Tokyo biyokimyasal araştırma hibe tarafından Vakfı, Tokyo, Japonya ve Stratejik Araştırma alanları için TUS (Tokyo Üniversitesi bilim) Fonu tarafından. Noriko Sawabe (Eczacılık Bilimleri Fakültesi, Tokyo Üniversitesi bilim) NMR spectra, Fukiko Hasegawa (Eczacılık Bilimleri Fakültesi, Tokyo Üniversitesi bilim) ölçümleri için kütle ölçüleri için teşekkür etmek istiyorum Spectra ve elemental analizler ölçümleri için Tomoko Matsuo (Fen ve teknoloji, Tokyo Üniversitesi Bilim Araştırma Enstitüsü).

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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Referências

  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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Keywords: 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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