Download PDF
Synlett 2018; 29(20): 2701-2706
DOI: 10.1055/s-0037-1611311
letter
© Georg Thieme Verlag Stuttgart · New York

Effect of Anomeric Configuration on Stereocontrolled α-Glycosylation of l-Fucose

Lihao Wang ◊
a   Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China   Email: caic@ouc.edu.cn
c   Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Fei Fan ◊
a   Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China   Email: caic@ouc.edu.cn
c   Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Haotian Wu
a   Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China   Email: caic@ouc.edu.cn
c   Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Lei Gao
a   Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China   Email: caic@ouc.edu.cn
c   Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Ping Zhang
a   Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China   Email: caic@ouc.edu.cn
c   Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Tiantian Sun
a   Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China   Email: caic@ouc.edu.cn
c   Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Chendong Yang
a   Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China   Email: caic@ouc.edu.cn
c   Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Guangli Yu
a   Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China   Email: caic@ouc.edu.cn
b   Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266003, P. R. of China
c   Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
,
Chao Cai*
a   Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China   Email: caic@ouc.edu.cn
b   Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266003, P. R. of China
c   Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
› Author AffiliationsThis work was financially supported by Fundamental Research Funds for the Central Universities (201762002), Natural Science Foundation of Shandong Province (ZR2016BB02), Primary Research and Development Plan of Shandong Province (2017GSF221002), Basic Research Funds for Application of Qingdao (17-1-1-63-jch), National Natural Science Foundation of China and NSFC-Shandong Joint Fund for Marine Science Research Centers (21602212, 31670811, U1606403), Major Science and Technology Projects in Shandong Province (2015ZDJS04002), China Postdoctoral Science Foundation (2016M590664, 2017T100519), Shandong Provincial Key Laboratory of Glycoscience Industry Alliance, Taishan Scholar Project Special Funds, as well as Qingdao Scientific and Technological Innovation Center for Marine Biomedicine Development Grant.
Further Information

Publication History

Received: 25 August 2018

Accepted after revision: 08 October 2018

Publication Date:
23 November 2018 (online)

    Permissions and Reprints All articles of this category


◊ These authors contributed equally to this work

Abstract

In this letter, we report an approach to the stereoselective α-glycosylation of l-fucose that is exemplified by effect of anomeric configuration. The neighboring group participation is not compatible with α-glycosylation of l-fucose, therefore the remote participation by 4-O-Bz was employed to control the formation of 1,2-cis-glycosidic bond. Furthermore, we found the anomeric configuration of fucose donor is crucial to stereoselectivity of the glycosylated products. The α/β-mixed products were generated by using β-anomeric donor while the glycosyl donor in α configuration yielded products in high α-selectivity possibly due to the distinct pathway to forming the key intermediates. This phenomenon supplies the basis for the synthesis of complicated natural carbohydrates containing fucose α-glycoside, such as fucoidans, fucosylated N-glycans, and fucosylated chondroitin sulfates, etc.

Key words

α-l-fucoside - stereoglycosylation - thioglycoside donor - anomeric configuration - remote participation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611311.
  • Supporting Information
 

  • References and Notes

    • 1a Perez C, Gerber S, Boilevin J, Bucher M, Darbre T, Aebi M, Reymond JL, Locher KP. Nature 2015; 524: 433
    • 1b Wang W, Wu J, Zhang X, Hao C, Zhao X, Jiao G, Shan X, Tai W, Yu G. Sci. Rep. 2017; 7: 40760
      CrossrefPubMed
    • 1c Hsu CH, Park S, Mortenson DE, Foley BL, Wang X, Woods RJ, Case DA, Powers ET, Wong CH, Dyson HJ, Kelly JW. J. Am. Chem. Soc. 2016; 138: 7636
      CrossrefPubMed
    • 2a Capila I, Linhardt RJ. Angew. Chem. Int. Ed. 2002; 41: 391
      PubMed
    • 2b Wen L, Zheng Y, Jiang K, Zhang M, Kondengaden SM, Li S, Huang K, Li J, Song J, Wang PG. J. Am. Chem. Soc. 2016; 138: 11473
      CrossrefPubMed
    • 2c Wen L, Liu D, Zheng Y, Huang K, Cao X, Song J, Wang PG. ACS Cent. Sci. 2018; 4: 451
      CrossrefPubMed
  • 3 Liu X, Liu Y, Hao J, Zhao X, Lang Y, Fan F, Cai C, Li G, Zhang L, Yu G. Molecules 2016; 21: 625
    CrossrefPubMed
  • 4 Li Q, Guo Z. Org. Lett. 2017; 19: 6558
    CrossrefPubMed
  • 5 Usvalampi A, Maaheimo H, Tossavainen O, Frey AD. Glycoconjugate J. 2018; 35: 31
    CrossrefPubMed
  • 6 Wen L, Edmunds G, Gibbons C, Zhang J, Gadi MR, Zhu H, Fang J, Liu X, Kong Y, Wang PG. Chem. Rev. 2018; 118: 8151
    CrossrefPubMed
  • 7 Pellissier H. Tetrahedron 2005; 61: 2947
    Crossref
  • 8 Solera C, Macchione G, Maza S, Kayser MM, Corzana F, de Paz JL, Nieto PM. Chem. Eur. J. 2016; 22: 2356
    CrossrefPubMed
  • 9 Schmidt RR, Behrendt M, Toepfer A. Synlett 1990; 694
    Article in Thieme Connect
  • 10 Nigudkar SS, Demchenko AV. Chem. Sci. 2015; 6: 2687
    CrossrefPubMed
  • 11 Nielsen MM, Pedersen CM. Chem. Rev. 2018; 118: 8285
    CrossrefPubMed
  • 12 Frihed TG, Bols M, Pedersen CM. Chem. Rev. 2015; 115: 3615
    CrossrefPubMed
    • 13a Sawant RC, Liao YJ, Lin YJ, Badsara SS, Luo SY. RSC Adv. 2015; 5: 19027
      Crossref
    • 13b Oh YI, Sheng GJ, Chang SK, Hsieh-Wilson LC. Angew. Chem. 2013; 125: 12012
      Crossref
    • 13c Zong C, Venot A, Li X, Lu W, Xiao W, Wilkes JS. L, Salanga CL, Handel TM, Wang L, Wolfert MA, Boons GJ. J. Am. Chem. Soc. 2017; 139: 9534
      CrossrefPubMed
    • 13d Guedes N, Kopitzki S, Echeverria B, Pazos R, Elosegui E, Calvo J, Reichardt NC. RSC Adv. 2015; 5: 9325
      Crossref
    • 14a Abronina PI, Zinin AI, Romashin DA, Malysheva NN, Chizhov AO, Kononov LO. Synlett 2015; 26: 2267
      Article in Thieme Connect
    • 14b Vermeer HJ, van Dijk CM, Kamerling JP, Vliegenthart JF. G. Eur. J. Org. Chem. 2001; 193
  • 15 Shan X, Liu X, Hao J, Cai C, Fan F, Dun Y, Zhao X, Liu X, Li C, Yu G. Int. J. Boil. Macromol. 2016; 82: 249
  • 16 De Castro C, Speciale I, Duncan G, Dunigan DD, Agarkova I, Lanzetta R, Sturiale L, Palmigiano A, Garozzo D, Molinaro A, Tonetti M, Etten JL. V. Angew.Chem. Int. Ed. 2016; 55: 654
  • 17 Zhao L, Wu M, Xiao C, Yang L, Zhou L, Gao N, Li Z, Chen J, Chen J, Liu J, Qin H, Zhao J. Proc. Natl. Acad. Sci. U.S.A. 2015; 112: 8284
    CrossrefPubMed
    • 18a Vinnitskiy DZ, Krylov VB, Ustyuzhanina NE, Dmitrenok AS, Nifantiev NE. Org. Biomol. Chem. 2016; 14: 598
      CrossrefPubMed
    • 18b Krylov VB, Kaskova ZM, Vinnitskiy DZ, Ustyuzhanina NE, Grachev AA, Chizhov AO, Nifantiev NE. Carbohyd. Res. 2011; 346: 540
      CrossrefPubMed
    • 18c Zlotina NS, Ustyuzhanina NE, Grachev AA, Gerbst AG, Nifantiev NE. J. Carbohyd. Chem. 2008; 27: 429
    • 19a Arafuka S, Koshiba N, Takahashi D, Toshima K. Chem. Commun. 2014; 50: 9831
      CrossrefPubMed
    • 19b Kasai A, Arafuka S, Koshiba N, Takahashi D, Toshima K. Org. Biomol. Chem. 2015; 13: 10556
      CrossrefPubMed
  • 20 Fan F, Cai C, Wang W, Gao L, Li J, Li J, Gu F, Sun T, Li J, Li C, Yu G. ACS Macro Lett. 2018; 7: 330
    CrossrefPubMed
  • 21 Ustyuzhanina N, Krylov V, Grachev A, Gerbst A, Nifantiev N. Synthesis 2006; 4017
    Article in Thieme Connect
  • 22 Lian G, Zhang X, Yu B. Carbohydr. Res. 2015; 403: 13
    CrossrefPubMed
  • 23 Fan F, Cai C, Gao L, Li J, Zhang P, Li G, Li C, Yu G. Polym. Chem. 2017; 8: 6709
  • 24 Fujiwara R, Horito S. Carbohydr. Res. 2011; 346: 2098
    CrossrefPubMed
  • 25 General Procedure for Fucosylation of 4α with AcceptorsTo a solution of compound 4α (10 mg, 0.0225 mmol, 1 equiv) and acceptor (0.0248–0.225 mmol, 1.1–10 equiv) in 500 μL anhyd Et2O with argon protection was added 4 Å MS. The mixture was stirred at room temperature for 0.5 h and then cooled to 0 °C, then NIS (10.1 mg, 0.045 mmol, 2 equiv) and TMSOTf (0.4 μL, 0.00225 mmol, 0.1 equiv) were added. The mixture was stirred for 0.5 h after which TLC indicated full conversion and quenched with Et3N. The mixture was filtered, evaporated, and purified by column chromatography to afford product.
  • 26 Analytical Data for Product 20 1H NMR (500 MHz, CDCl3): δ = 8.03 (d, J = 8.1 Hz, 2 H), 7.60 (t, J = 7.4 Hz, 1 H), 7.47 (t, J = 7.7 Hz, 2 H), 7.33–7.27 (m, 5 H), 6.23 (s, 2 H), 5.50 (d, J = 3.0 Hz, 1 H), 5.35 (dd, J = 10.5, 3.2 Hz, 1 H), 4.93 (d, J = 3.4 Hz, 1 H), 4.60 (dd, J = 27.2, 12.1 Hz, 2 H), 4.26 (q, J = 6.5 Hz, 1 H), 3.91 (dd, J = 10.5, 3.5 Hz, 1 H), 3.85–3.80 (m, 1 H), 3.78–3.70 (m, 3 H), 3.26 (s, 1 H), 3.19 (s, 1 H), 2.60 (dd, J = 23.4, 7.0 Hz, 2 H), 1.91 (s, 3 H), 1.42 (d, J = 10.0 Hz, 1 H), 1.36 (d, J = 10.1 Hz, 1 H), 1.16 (d, J = 6.5 Hz, 3 H). 13C NMR (126 MHz, CDCl3): δ = 177.98, 177.95, 170.01, 165.98, 138.13, 137.82, 137.68, 133.22, 129.77, 129.67, 128.48, 128.34, 127.75, 127.69, 97.27, 73.49, 72.98, 72.15, 70.02, 65.02, 63.58, 47.83, 45.19, 42.89, 37.81, 20.83, 16.03. HRMS: m/z calcd for [C33H35NNaO9]+: 612.2204; found: 612.2201.
  • 27 Nomura K, Abdellatif MM. Polymer 2010; 51: 1861
    Crossref
  • 28 Analytical Data for Product 23 1H NMR (500 MHz, CDCl3): δ = 8.08 (d, J = 7.3 Hz, 2 H), 7.64 (t, J = 7.4 Hz, 1 H), 7.51 (t, J = 7.7 Hz, 2 H), 7.37–7.30 (m, 5 H), 5.82 (d, J = 3.6 Hz, 1 H), 5.53 (d, J = 2.6 Hz, 1 H), 5.37 (dd, J = 10.6, 3.2 Hz, 1 H), 5.01 (d, J = 3.5 Hz, 1 H), 4.75 (d, J = 12.1 Hz, 1 H), 4.60 (d, J = 5.6 Hz, 1 H), 4.56 (d, J = 12.2 Hz, 1 H), 4.41–4.36 (m, 1 H), 4.34 (d, J = 3.6 Hz, 1 H), 4.31 (d, J = 3.1 Hz, 1 H), 4.17 (dd, J = 8.6, 6.2 Hz, 1 H), 4.11 (dd, J = 9.1, 3.1 Hz, 1 H), 4.03–3.99 (m, 2 H), 1.96 (s, 3 H), 1.50 (s, 3 H), 1.42 (s, 3 H), 1.37 (s, 3 H), 1.29 (s, 3 H), 1.14 (d, J = 6.5 Hz, 3 H).13C NMR (126 MHz, CDCl3): δ = 170.12, 166.05, 138.16, 133.28, 129.80, 129.72, 128.53, 128.49, 127.97, 127.68, 111.93, 109.22, 105.38, 96.00, 82.31, 81.08, 78.34, 73.80, 73.53, 72.20, 72.09, 70.43, 67.97, 65.27, 26.95, 26.87, 26.24, 25.36, 20.87, 15.88. HRMS: m/z calcd for [C34H42NaO12]+: 665.2568; found: 665.2565.
    • 29a Zhou J, Yang L, Hu W. J. Org. Chem. 2014; 79: 4718
      CrossrefPubMed
    • 29b Li CY, Liu GJ, Du W, Zhang Y, Xing GW. Tetrahedron Lett. 2017; 58: 2109
      Crossref
    • 29c Zong C, Li Z, Sun T, Wang P, Ding N, Li Y. Carbohydr. Res. 2010; 345: 1522
      CrossrefPubMed
    • 29d Zhang X, Yao W, Xu X, Sun H, Zhao J, Meng X, Wu M, Li Z. Chem. Eur. J. 2018; 24: 1694
      CrossrefPubMed
    • 29e Hua Y, Gu G, Du Y. Carbohydr. Res. 2004; 339: 867
      CrossrefPubMed