Recent Advances in Protection-Free Glycosylations

doi:10.6023/cjoc202211024

Abstract

Carbohydrates play a key role in many life activities, such as cell wall composition, energy storage and biological recognition. Development of highly regio- and stereo-selective glycosylation reactions is a central topic of current carbohydrate chemistry. The traditional glycosylation protocol usually requires the orthogonal protecting chemistry to obtain the selectivity of glycosylation reactions. Recent progress in protecting-group free strategies can provide a simple and mild approach to the chemo-selective construction of glycosidic bonds in oligosaccharides or glycoconjugates in aqueous conditions. The latest advances in protection-free chemical glycosylations are summarized, including the direct anomeric activation strategy developed by our group.

Key words: chemical glycosylation, protection-free, direct anomeric activation, carbohydrate chemistry

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Gefei Li, Jie Jing, Zhenyang Luo, Juan Mo, Decai Xiong, Xinshan Ye. Recent Advances in Protection-Free Glycosylations[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1991-2001.

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Fig. & Tab. 11

Scheme 1. General glycosylation process with or without protecting chemistry

Figure 1. Glycosylation mechanism: (A) enzymatic process based on H-bonding interaction; (B) chemical process relied on metal ion binding

Scheme 2. Calcium ion mediated aqueous protecting-group free glycosylation using fluoroglycoside donors

Scheme 3. Regio- and stereo-selective glycosylation using a boronic acid catalyst

Scheme 4. Direct anomeric activation strategy for the synthesis of glycosyl donors used in the chemo-enzymatic glycosylation

Scheme 5. Development of DBT-glycosyl donors used for protecting-group free glycosylation

Scheme 6. Concept of dehydrative process in water

Scheme 7. Applications of Shoda’s reagent in direct anomeric activation

Scheme 8. Current progress in Fischer glycosylation

Scheme 9. Other protecting-group free glycosylation reactions

Figure 2. Production of bioactive carbohydrates based on the concept of “Glyco-chemistry Cycle System”

References 65

[1]	Clausen, T. M.; Sandoval, D. R.; Spliid, C. B.; Pihl, J.; Perrett, H. R.; Painter, C. D.; Narayanan, A.; Majowicz, S. A.; Kwong, E. M.; McVicar, R. N.; Thacker, B. E.; Glass, C. A.; Yang, Z.; Torres, J. L.; Golden, G. J.; Bartels, P. L.; Porell, R. N.; Garretson, A. F.; Laubach, L.; Feldman, J.; Yin, X.; Pu, Y.; Hauser, B. M.; Caradonna, T. M.; Kellman, B. P.; Martino, C.; Gordts, P.; Chanda, S. K.; Schmidt, A. G.; Godula, K.; Leibel, S. L.; Jose, J.; Corbett, K. D.; Ward, A. B.; Carlin, A. F.; Esko, J. D. Cell 2020, 183, 1043. doi: 10.1016/j.cell.2020.09.033 pmid: 32970989
[2]	Moradi, S. V.; Hussein, W. M.; Varamini, P.; Simerska, P.; Toth, I. Chem. Sci. 2016, 7, 2492. doi: 10.1039/C5SC04392A
[3]	Qin, X.; Ye, X.-S. Chin. J. Chem. 2021, 39, 531. doi: 10.1002/cjoc.v39.3
[4]	Yu, B. Acc. Chem. Res. 2018, 51, 507. doi: 10.1021/acs.accounts.7b00573
[5]	Guo, J.; Ye, X.-S. Molecules 2010, 15, 7235. doi: 10.3390/molecules15107235
[6]	Villadsen, K.; Martos-Maldonado, M. C.; Jensen, K. J.; Thygesen, M. B. ChemBioChem 2017, 18, 574. doi: 10.1002/cbic.201600582 pmid: 28067438
[7]	Bojarova, P.; Rosencrantz, R. R.; Elling, L.; Kren, V. Chem. Soc. Rev. 2013, 42, 4774. doi: 10.1039/c2cs35395d
[8]	Mukaiyama, T.; Murai, Y.; Shoda, S. Chem. Lett. 1981, 10, 431. doi: 10.1246/cl.1981.431
[9]	Nicolaou, K. C.; Dolle, R. E.; Papahatjis, D. P. J. Am. Chem. Soc. 1984, 106, 4189. doi: 10.1021/ja00327a021
[10]	Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693. doi: 10.1021/ja00165a084
[11]	Kobayashi, S.; Kashiwa, K.; Kawasaki, T.; Shoda, S. J. Am. Chem. Soc. 1991, 113, 3079. doi: 10.1021/ja00008a042
[12]	Banait, N. S.; Jencks, W. P. J. Am. Chem. Soc. 1991, 113, 7951. doi: 10.1021/ja00021a021
[13]	Banait, N. S.; Jencks, W. P. J. Am. Chem. Soc. 1991, 113, 7958. doi: 10.1021/ja00021a022
[14]	Pelletier, G.; Zwicker, A.; Allen, C. L.; Schepartz, A.; Miller, S. J. J. Am. Chem. Soc. 2016, 138, 3175. doi: 10.1021/jacs.5b13384
[15]	Wadzinski, T. J.; Steinauer, A.; Hie, L.; Pelletier, G.; Schepartz, A.; Miller, S. J. Nat. Chem. 2018, 10, 644. doi: 10.1038/s41557-018-0041-8 pmid: 29713033
[16]	Wen, P.; Jia, P.; Fan, Q.; McCarty, B. J.; Tang, W. ChemSusChem 2022, 15, e202102483.
[17]	Zhang, G. L.; Gadi, M. R.; Cui, X.; Liu, D.; Zhang, J.; Saikam, V.; Gibbons, C.; Wang, P. G.; Li, L. Green Chem. 2021, 23, 2907. doi: 10.1039/D1GC00098E
[18]	Takahashi, D.; Tanaka, M.; Toshima, K. Trends Glycosci. Glyc. 2018, 30, E55. doi: 10.4052/tigg.1817.2E
[19]	Oshima, K.; Kitazono, E.-i.; Aoyama, Y. Tetrahedron Lett. 1997, 38, 5001. doi: 10.1016/S0040-4039(97)01070-8
[20]	Oshima, K.; Aoyama, Y. J. Am. Chem. Soc. 1999, 121, 2315. doi: 10.1021/ja982395g
[21]	Gouliaras, C.; Lee, D.; Chan, L.; Taylor, M. S. J. Am. Chem. Soc. 2011, 133, 13926. doi: 10.1021/ja2062715
[22]	Nakagawa, A.; Tanaka, M.; Hanamura, S.; Takahashi, D.; Toshima, K. Angew. Chem., Int. Ed. 2015, 54, 10935. doi: 10.1002/anie.201504182
[23]	Tanaka, M.; Nakagawa, A.; Nishi, N.; Iijima, K.; Sawa, R.; Takahashi, D.; Toshima, K. J. Am. Chem. Soc. 2018, 140, 3644. doi: 10.1021/jacs.7b12108
[24]	Tanaka, M.; Nashida, J.; Takahashi, D.; Toshima, K. Org. Lett. 2016, 18, 2288. doi: 10.1021/acs.orglett.6b00926
[25]	Shoda, S.; Uyama, H.; Kadokawa, J.; Kimura, S.; Kobayashi, S. Chem. Rev. 2016, 116, 2307. doi: 10.1021/acs.chemrev.5b00472
[26]	Shoda, S. Proc. Jpn. Acad. Ser. B 2017, 93, 125. doi: 10.2183/pjab.93.008
[27]	Tanaka, T.; Noguchi, M.; Kobayashi, A.; Shoda, S. Chem. Comm. 2008, 17, 2016.
[28]	Kobayashi, A.; Tanaka, T.; Watanabe, K.; Ishihara, M.; Noguchi, M.; Okada, H.; Morikawa, Y.; Shoda, S. Bioorg. Med. Chem. Lett. 2010, 20, 3588. doi: 10.1016/j.bmcl.2010.04.122 pmid: 20529686
[29]	Tanaka, T.; Noguchi, M.; Watanabe, K.; Misawa, T.; Ishihara, M.; Kobayashi, A.; Shoda, S. Org. Biomol. Chem. 2010, 8, 5126. doi: 10.1039/c0ob00190b
[30]	Noguchi, M.; Nakamura, M.; Ohno, A.; Tanaka, T.; Kobayashi, A.; Ishihara, M.; Fujita, M.; Tsuchida, A.; Mizuno, M.; Shoda, S. Chem. Commun. 2012, 48, 5560. doi: 10.1039/c2cc30946g
[31]	Tanaka, T.; Matsuura, A.; Aso, Y.; Ohara, H. J. Appl. Glycosci. 2020, 67, 119. doi: 10.5458/jag.jag.JAG-2020_0010
[32]	Fujimoto, Y.; Mitsunobe, K.; Fujiwara, S.; Mori, M.; Hashimoto, M.; Suda, Y.; Kusumoto, S.; Fukase, K. Org. Biomol. Chem. 2013, 11, 5034. doi: 10.1039/c3ob40899j pmid: 23804153
[33]	Tanaka, T.; Kikuta, N.; Kimura, Y.; Shoda, S. Chem. Lett. 2015, 44, 846. doi: 10.1246/cl.150201
[34]	Ishihara, M.; Takagi, Y.; Li, G.; Noguchi, M.; Shoda, S. Chem. Lett. 2013, 42, 1235. doi: 10.1246/cl.130646
[35]	Li, G.; Luo, Y.; Mo, J.; Noguchi, M.; Jing, J.; Luo, Z.; Shoda, S.; Ye, X.-S. Chin. Chem. Lett. 2023, 34, 107754. doi: 10.1016/j.cclet.2022.107754
[36]	Noguchi, M.; Tanaka, T.; Gyakushi, H.; Kobayashi, A.; Shoda, S. J. Org. Chem. 2009, 74, 2210. doi: 10.1021/jo8024708 pmid: 19203234
[37]	Li, G.; Noguchi, M.; Serizawa, K.; Shoda, S. Chimia 2018, 72, 874. doi: 10.2533/chimia.2018.874
[38]	Fairbanks, A. J. Carbohydr. Res. 2021, 499, 108197. doi: 10.1016/j.carres.2020.108197
[39]	Li, C.; Wang, L.-X. Chem. Rev. 2018, 118, 8359. doi: 10.1021/acs.chemrev.8b00238
[40]	Huang, W.; Giddens, J.; Fan, S. Q.; Toonstra, C.; Wang, L.-X. J. Am. Chem. Soc. 2012, 134, 12308. doi: 10.1021/ja3051266 pmid: 22747414
[41]	Tanaka, T.; Nagai, H.; Noguchi, M.; Kobayashi, A.; Shoda, S. Chem. Commun. 2009, 45, 3378.
[42]	Li, G.; Ma, W.; Mo, J.; Cheng, B.; Shoda, S.; Zhou, D.; Ye, X.-S. ACS Appl. Mater. Interfaces 2021, 13, 46260. doi: 10.1021/acsami.1c11561
[43]	Meguro, Y.; Noguchi, M.; Li, G.; Shoda, S. Org. Lett. 2018, 20, 76. doi: 10.1021/acs.orglett.7b03400
[44]	Meguro, Y.; Noguchi, M.; Li, G.; Shoda, S. Tetrahedron Lett. 2020, 61, 152198. doi: 10.1016/j.tetlet.2020.152198
[45]	Li, G.; Dao, Y.; Mo, J.; Dong, S.; Shoda, S.; Ye, X.-S. CCS Chem. 2022, 4, 1930. doi: 10.31635/ccschem.021.202101115
[46]	Li, G.; Noguchi, M.; Kashiwagura, H.; Tanaka, Y.; Serizawa, K.; Shoda, S. Tetrahedron Lett. 2016, 57, 3529.
[47]	Li, G.; Noguchi, M.; Nakamura, K.; Hayasaka, R.; Tanaka, Y.; Shoda, S. Tetrahedron Lett. 2018, 59, 3428. doi: 10.1016/j.tetlet.2018.08.005
[48]	Li, G.; Noguchi, M.; Arisaka, G.; Tanaka, Y.; Shoda, S. Org. Biomol. Chem. 2021, 19, 3134. doi: 10.1039/D1OB00311A
[49]	Sinnott, M. L. Chem. Rev. 1990, 90, 1171. doi: 10.1021/cr00105a006
[50]	Qiu, X.; Fairbanks, A. J. Org. Biomol. Chem. 2020, 18, 7355. doi: 10.1039/D0OB01727B
[51]	Guchhait, G.; Misra, A. K. Catal. Comm. 2011, 14, 52. doi: 10.1016/j.catcom.2011.07.016
[52]	Gorityala, B. K.; Ma, J.; Pasunooti, K. K.; Cai, S.; Liu, X. Green Chem. 2011, 13, 573. doi: 10.1039/c0gc00883d
[53]	Javier Muñoz, F.; André, S.; Gabius, H.-J.; Sinisterra, J. V.; Hernáiz, M. J.; Linhardt, R. J. Green Chem. 2009, 11, 373. doi: 10.1039/B814171A
[54]	Schmanlisch, S.; Mahrwald, R. Org. Lett. 2013, 15, 5854. doi: 10.1021/ol402914v
[55]	Izumi, M.; Fukase, K.; Kusumoto, S. Biosci. Biotechnol. Biochem. 2002, 66, 211. doi: 10.1271/bbb.66.211
[56]	Shaikh, N.; Russo, L.; Cipolla, L.; Nicotra, F. Mol. Diversity 2011, 15, 341. doi: 10.1007/s11030-010-9281-2
[57]	Mamidyala, S. K.; Finn, M. G. J. Org. Chem. 2009, 74, 8417. doi: 10.1021/jo901857x pmid: 19827757
[58]	Meng, B.; Zhu, Z.; Baker, D. C. Org. Biomol. Chem. 2014, 12, 5182. doi: 10.1039/c4ob00626g pmid: 24915049
[59]	Gudmundsdottir, A. V.; Nitz, M. Org. Lett. 2008, 10, 3461. doi: 10.1021/ol801232f pmid: 18616337
[60]	Williams, R. J.; Paul, C. E.; Nitz, M. Carbohydr. Res. 2014, 386, 73. doi: 10.1016/j.carres.2013.08.019
[61]	Edgar, L. J. G.; Dasgupta, S.; Nitz M. Org. Lett. 2012, 14, 4226. doi: 10.1021/ol3019083
[62]	Alexander, S. R.; Fairbanks, A. J. Org. Biomol. Chem. 2016, 14, 6679. doi: 10.1039/c6ob01069e pmid: 27327112
[63]	Wan, L.; Zhang, X.; Zou, Y.; Shi, R.; Cao, J.; Xu, S.; Deng, L.; Zhou, L.; Gong, Y.; Shu, X.; Lee, G.-Y.; Ren, H.; Dai, L.; Qi, S.; Houk, K.-N.; Niu, D. J. Am. Chem. Soc. 2021, 143, 11919. doi: 10.1021/jacs.1c05156
[64]	Takeuchi, H.; Fujimori, Y.; Uedda, Y.; Shibayama, H.; Nagaishi, M.; Yoshimura, T.; Sasamori, T.; Tokitoh, N.; Furuta, T.; Kawabata, T. Org. Lett. 2020, 22, 4754. doi: 10.1021/acs.orglett.0c01549
[65]	Yao, W.; Xiong, D.-C.; Yang, Y.; Geng, C.; Cong, Z.; Li, F.; Li, B.-H.; Qin, X.; Wang, L-N.; Xue, W.-Y.; Yu, N.; Zhang, H.; Wu, X.; Liu, M.; Ye, X.-S. Nat. Synth. 2020, 854.

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