Abstract
Stereoselective synthesis of α-sialosides by the glycosylation reaction (sialylation) is an important task in carbohydrate chemistry. Using quantum chemical calculations, the conformations of the sialyl cation formed from the sialyl donor under conditions of sialylation reaction were studied. Although the "axial conformation" of sialyl cation itself is energetically unfavorable, it is possible to stabilize it through the participation of O- and N-acyl protective groups. The obtained results open the possibility to modulate the stereoselectivity of sialylation by directed variation of the nature of protective groups in the sialyl donor molecule. 2
Similar content being viewed by others
References
X. Chen, A. Varki, ACS Chem. Biol., 2010, 5, 163–176; DOI: 10.1021/cb900266r.
A. Varki, Nature, 2007, 446, 1023–1029; DOI: 10.1038/nature05816.
S. Sakarya, C. Göktürk, T. Öztürk, M. B. Ertugrul, FEMS Immunol. Med. Microbiol., 2010, 58, 330–335; DOI: 10.1111/j.1574-695X.2010.00650.x.
R. A. Medina, A. García-Sastre, Nat. Rev. Microbiol., 2011, 9, 590–603; DOI: 10.1038/nrmicro2613.
J. E. Stencel-Baerenwald, K. Reiss, D. M. Reiter, T. Stehle, T. S. Dermody, Nat. Rev. Microbiol., 2014, 12, 739–749; DOI: 10.1038/nrmicro3346.
C. Bull, M. A. Stoel, M. H. den Brok, G. J. Adema, Cancer Res., 2014, 74, 3199–3204; DOI: 10.1158/0008-5472.Can-14-0728.
O. M. T. Pearce, H. Läubli, Glycobiology, 2016, 26, 111–128; DOI: 10.1093/glycob/cwv097.
H. Ando, Biosci. Biotechnol. Biochem., 2015, 79, 343–346; DOI: 10.1080/0 9168451.2014.990228.
C. Navuluri, D. Crich, in Glycochemical Synthesis: Strategies and App lications, Eds S.-C. Hung, M. M. L. Zulueta, John Wiley and Sons, Inc., Hoboken, 2016, p. 131–154.
B. Sun, Curr. Org. Chem., 2016, 20, 1465–1476; DOI: 10.2174/138527282014160419234226.
L. O. Kononov, N. N. Malysheva, E. G. Kononova, O. G. Garkusha, Russ. Chem. Bull., 2006, 55, 1311–1313; DOI: 10.1007/s11172-006-0419-4.
L. O. Kononov, N. N. Malysheva, E. G. Kononova, A. V. Orlova, Eur. J. Org. Chem., 2008, 3251–3255; DOI: 10.1002/ejoc.200800324.
L. O. Kononov, N. N. Malysheva, A. V. Orlova, Eur. J. Org. Chem., 2009, 611–616; DOI: 10.1002/ejoc.200801017.
L. O. Kononov, N. N. Malysheva, A. V. Orlova, A. I. Zinin, T. V. Laptinskaya, E. G. Kononova, N. G. Kolotyrkina, Eur. J. Org. Chem., 2012, 1926–1934; DOI: 10.1002/ej oc.201101613.
L. O. Kononov, in Advances in Chemistry Research, Ed. J. C. Taylor, Nova Science Publishers, Inc., Hauppauge, NY, 2013, p. 143–178; https://www.novapublishers.com/catalog/product_info.php?products_id=41681.
H. M. Christensen, S. Oscarson, H. H. Jensen, Carbohydr. Res., 2015, 408, 51–95; DOI: 10.1016/j.carres.2015.02.007.
D. K. Ress, R. J. Linhardt, Curr. Org. Synth., 2004, 1, 31–46; DOI: 10.2174/1570179043485448.
L. K. Mydock, A. V. Demchenko, Org. Biomol. Chem., 2010, 8, 497–510; DOI: 10.1039/b916088d.
H. Satoh, T. Nukada, Trends Glycosci. Glycotechnol., 2014, 26, 11–27; DOI: 10.4052/tigg.26.11.
L. Bohé, D. Crich, Carbohydr. Res., 2015, 403, 48–59; DOI: 10.101 6/j.carres.2014.06.020.
L. Bohé, D. Crich, Nat. Chem., 2016, 8, 99–100; DOI: 10.1038/nchem.2436.
B. Hagen, S. van der Vorm, T. Hansen, G. A. van der Marel, J. D. C. Codée, in Selective Glycosylations: Synthetic Methods and Catalysts, Ed. C. S. Bennett, Wiley-VCH V erlag GmbH and Co. KGaA, Weinheim, 2017, p. 3–28.
C. De Meo, C. E. Wallace, S. A. Geringer, Org. Lett., 2014, 16, 2676–2679; DOI: 10.1021/ol500917k.
H. D. Premathilake, C. P. Gobble, P. Pornsuriyasak, T. Hardimon, A. V. Demchenko, C. De Meo, Org. Lett., 2012, 14, 1126–1129; DOI: 10.1021/ol3000475.
S. Escopy, S. A. Geringer, C. De Meo, Org. Lett., 2017, 19, 2638–2641; DOI: 10.1021/acs.orglett.7b00976.
M. T. Yang, K. A. Woerpel, J. Org. Chem., 2009, 74, 545–553; DOI: 10.1021/jo8017846.
M. T. C. Walvoort, J. Dinkelaar, L. J. van den Bos, G. Lodder, H. S. Overkleeft, J. D. C. Codée, G. A. van der Marel, Carbohydr. Res., 2010, 345, 1252–1263; DOI: 10.1016/j. carres.2010.02.027.
A. Imamura, N. Matsuzawa, S. Sakai, T. Udagawa, S. Nakashima, H. Ando, H. Ishida, M. Kiso, J. Org. Chem., 2016, 81, 9086–9104; DOI: 10.1021/acs.joc.6b01685.
K. Furuhata, H. Ogura, Chem. Pharm. Bull., 1992, 40, 3197–3200; DOI: 10.1248/cpb.40.3197.
K. H. Asressu, C. C. Wang, Carbohydr. Res., 2017, 453–454, 44–53; DOI: 10. 1016/j.carres.2017.10.007.
S. Sato, K. Furuhata, H. Ogura, Chem. Pharm. Bull., 1988, 36, 4678–4688; DOI: 10.1248/cpb.36.4678.
N. Sugiyama, K. Sugai, N. Yamada, M. Goto, C. Ban, K. Furuhata, H. Takayanagi, H. Ogura, Chem. Pharm. Bull., 1988, 36, 1147–1152; DOI: 10.1248/cpb.36.1147.
R. Colombo, M. Anastasia, P. Rota, P. Allevi, Chem. Commun., 2008, 5517–5519; DOI: 10.1039/b810447f.
P. Allevi, P. Rota, R. Scaringi, R. Colombo, M. Anastasia, J. Org. Chem., 2010, 75, 5542–5548; DOI: 10.1021/jo100732j.
K. S. Kim, D.-H. Suk, Top. Curr. Chem., 2011, 301, 109–140; DOI: 10.1007/128_2010_107.
J. Kalikanda, Z. Li, J. Org. Chem., 2011, 76, 5207–5218; DOI: 10.1021/jo1025157.
B. S. Komarova, N. E. Ustyuzhanina, Y. E. Tsvetkov, N. E. Nifantiev, in Modern Synt hetic Methods in Carbohydrate Chemistry: From Monosaccharides to Complex Glycoconjugates, Eds D. B. Werz, S. Vidal, Wil.
D. Yao, Y. Liu, S. Yan, Y. Li, C. Hu, N. Ding, Chem. Commun., 2017, 53, 2986–2989; DOI: 10.1039/c7cc00274b.
B. Yang, W. Z. Yang, S. Ramadan, X. F. Huang, Eur. J. Org. Chem., 2018, 1075–1096; DOI: 10.1002/ejoc. 201701579.
C. De Meo, M. N. Kamat, A. V. Demchenko, Eur. J. Org. Chem., 2005, 706–711; DOI: 10.1002/ejoc.200400616.
W. Huang, Y.-Y. Zhou, X.-L. Pan, X.-Y. Zhou, J.-C. Lei, D.-M. Liu, Y. Chu, J.-S. Yang, J. Am. Chem. Soc., 2018, 140, 3574–3582; DOI: 10.1021/jacs.7b09461.
D. Crich, W. Li, Org. Lett., 2006, 8, 959–962; DOI: 10.1021/ol060030s.
C. Adamo, V. Barone, J. Chem. Phys., 1999, 110, 6158–6170; DOI: 10.1063/1.478522.
S. Grimme, J. Antony, S. Ehrlich, H. Krieg, J. Chem. Phys., 2010, 132, 154104; DOI: 10.1063/1.3382344.
T. H. Dunning, Jr., K. A. Peterso n, A. K. Wilson, J. Chem. Phys., 2001, 114, 9244–9253; DOI: 10.1063/1.1367373.
A. V. Marenich, C. J. Cramer, D. G. Truhlar, J. Phys. Chem. B, 2009, 113, 6378–6396; DOI: 10.1021/jp810292n.
M. S. Gordon, M. W. Schmidt, in Theory and Applications of Computational Chemistry: The First Forty Years, Eds C. E. Dykstra, G. Frenking, K. S. Kim, G. E. Scuseria, Elsevier, Amsterdam, 2005, p. 1167–1189.
M. Marianski, A. Supady, T. Ingram, M. Schneider, C. Baldauf, J. Chem. Theory Comput., 2016, 12, 6157–6168; DOI: 10.1021/acs.jctc.6b00876.
M. G. Medvedev, I. S. Bushmarinov, J. W. Sun, J. P. Perdew, K. A. Lyssenko, Science, 2017, 355, 49–52; DOI: 10.1126/science.aah5975.
A. Bérces, D. M. Whitfield, T. Nukada, Tetrahedron, 2001, 57, 477–491; DOI: 10.1016/S0040-4020(00)01019-X.
S. Komba, C. Galustian, H. Ishida, T. Feizi, R. Kannagi, M. Kiso, Angew. Chem., Int. Ed. Engl., 1999, 38, 1131–1133; DOI: 10.1002/(SICI)1521-3773(19990419)38:8<1131::AIDANIE1131>3.0.CO;2-B.
C. De Meo, A. V. Demchenko, G.-J. Boons, J. Org. Chem., 2001, 66, 5490–5497; DOI: 10.1021/jo010345f.
C. De Meo, A. V. Demchenko, G.-J. Boons, Austr. J. Chem., 2002, 55, 131–134; DOI: 10.1071/ch02018.
Y. Pan, P. Chefalo, N. Nagy, C. Harding, Z. Guo, J. Med. Chem., 2005, 48, 875–883; DOI: 10.1021/jm0494422.
C.-C. Lin, K.-T. Huang, C.-C. Lin, Org. Lett., 2005, 7, 4169–4172; DOI: 10.1021/ol0515210.
N. M. Podvalnyy, N. N. Malysheva, M. V. Panova, A. I. Zinin, A. O. Chizhov, A. V. Orlova, L. O. Kononov, Carbohydr. Res., 2017, 451, 12–28; DOI: 10.1016/j.carres. 2017.09.002.
A. R. Ionescu, D. M. Whitfield, M. Z. Zgierski, T. Nukada, Carbohydr. Res., 2006, 341, 2912–2920; DOI: 10.1016/j. carres.2006.09.027.
T. Hosoya, T. Takano, P. Kosma, T. Rosenau, J. Org. Chem., 2014, 79, 7889–7894; DOI: 10.1021/jo501012s.
F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1987, S1–S19; DOI: 10.1039/p298700000s1.
T. Aoyagi, S. Ohira, S. Fuse, J. Uzawa, Y. Yamaguchi, H. Tanaka, Chem. Eur. J., 2016, 22, 6968–6973; DOI: 10.1002/chem.201601031.
P. K. Kancharla, D. Crich, J. Am. Chem. Soc., 2013, 135, 18999–19007; DOI: 10.1021/ja410683y.
S. Dharuman, D. Crich, Chem. Eur. J., 2016, 22, 4535–4542; DOI: 10.1002/chem.201505019.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1573–1579, September, 2018.
Rights and permissions
About this article
Cite this article
Panova, M.V., Orlova, A.V. & Kononov, L.O. Stabilization of sialyl cation in axial conformation assisted by remote acyl groups. Russ Chem Bull 67, 1573–1579 (2018). https://doi.org/10.1007/s11172-018-2260-y
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-018-2260-y