Saccharide Recognition by a Three-Arm-Shaped Host Having Preorganized Three-Dimensional Hydrogen-Bonding Sites.
glycosides
host-guest systems
hydrogen bonds
molecular recognition
solid-liquid extraction
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
07 Jan 2021
07 Jan 2021
Historique:
received:
11
09
2020
pubmed:
1
10
2020
medline:
1
10
2020
entrez:
30
9
2020
Statut:
ppublish
Résumé
Generally, cage-shaped hosts for saccharides can bind strongly to guest molecules because of the three-dimensional preorganized hydrogen-bonding sites. However, the preparation of cage molecules is often difficult because of the low yield of the macrocyclization step. Here, we report a three-arm-shaped molecule possessing pyridine-acetylene-phenol units as a new kind of host having a preorganized three-dimensional hydrogen-bonding site. This three-arm-shaped host was readily prepared compared to a cage-shaped analogue. This host associated with lipophilic glycosides to form chiral complexes, and the association constants were sufficiently high as to be comparable to those of the cage-shaped analogue. Furthermore, this host extracted native monosaccharides into a lipophilic solvent.
Identifiants
pubmed: 32996641
doi: 10.1002/chem.202004147
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
785-793Subventions
Organisme : Core Research for Evolutional Science and Technology
ID : JPMJCR1522
Organisme : Japan Society for the Promotion of Science
ID : JP18H04243
Organisme : Mukai Science and Technology Foundation
Organisme : Japan Science Society
Informations de copyright
© 2020 Wiley-VCH GmbH.
Références
For recent examples of selective recognition for non-sugar guests by monomolecular cage-shaped hosts, see:
Y. Liu, W. Zhao, C.-H. Chen, A. H. Flood, Science 2019, 365, 159-161;
D.-H. Tuo, Y.-F. Ao, Q.-Q. Wang, D.-X. Wang, Org. Lett. 2019, 21, 7158-7162;
J. H. Oh, J. H. Kim, D. S. Kim, H. J. Han, V. M. Lynch, J. L. Sessler, S. K. Kim, Org. Lett. 2019, 21, 4336-4339;
Y. Shi, K. Cai, H. Xiao, Z. Liu, J. Zhou, D. Shen, Y. Qiu, Q.-H. Guo, C. Stern, M. R. Wasielewsiki, F. Diederich, W. A. Goddard III, J. F. Stoddart, J. Am. Chem. Soc. 2018, 140, 13835-13842.
For recent examples of selective recognition for native saccharides by artificial host, see:
O. Francesconi, M. Martinucci, L. Badii, C. Nativi, S. Roelens, Chem. Eur. J. 2018, 24, 6828-6836;
J. Y. Hwang, H.-G. Jeon, Y. R. Choi, J. Kim, P. Kang, S. Lee, K.-S. Jeong, Org. Lett. 2017, 19, 5625-5628;
M. Yamashina, M. Akita, T. Hasegawa, S. Hayashi, M. Yoshizawa, Sci. Adv. 2017, 3, e1701126;
N. Chandramouli, Y. Ferrand, G. Lautrette, B. Kauffmann, C. D. Mackereth, M. Laguerre, D. Dubreuil, I. Huc, Nat. Chem. 2015, 7, 334-341;
Y. Jang, R. Natarajan, Y. H. Ko, K. Kim, Angew. Chem. Int. Ed. 2014, 53, 1003-1007;
Angew. Chem. 2014, 126, 1021-1025.
For examples of glucose selective recognition by cage-shaped hosts, see:
R. A. Tromans, T. S. Carter, L. Chabanne, M. P. Crump, H. Li, J. V. Matlock, M. G. Orchard, A. P. Davis, Nat. Chem. 2019, 11, 52-56;
C. Ke, H. Destecroix, M. P. Crump, A. P. Davis, Nat. Chem. 2012, 4, 718-723.
For recent reviews of artificial hosts for saccharides, see:
A. P. Davis, Chem. Soc. Rev. 2020, 49, 2531-2545;
O. Francesconi, S. Roelens, ChemBioChem 2019, 20, 1329-1346;
C. E. Miron, A. Petitjean, ChemBioChem 2015, 16, 365-379;
M. Mazik, RSC Adv. 2012, 2, 2630-2642;
S. Jin, Y. Cheng, S. Reid, M. Li, B. Wang, Med. Res. Rev. 2010, 30, 171-257.
For recent examples of saccharide recognition by cage hosts, see:
J. Lippe, M. Mazik, J. Org. Chem. 2015, 80, 1427-1439;
A. Schmitt, O. Perraud, E. Payet, B. Chatelet, B. Bousquet, M. Valls, D. Padula, L. D. Bari, J.-P. Dutasta, A. Martinez, Org. Biomol. Chem. 2014, 12, 4211-4217;
O. Francesconi, M. Gentili, C. Nativi, A. Ardá, K. F. Cañada, J. Jiménez-Barbero, S. Roelens, Chem. Eur. J. 2014, 20, 6081-6091.
R. Ning, H. Zhou, S.-X. Nie, Y.-F. Ao, D.-X. Wang, Q.-Q. Wang, Angew. Chem. Int. Ed. 2020, 59, 10894-10898;
Angew. Chem. 2020, 132, 10986-10990;
R. Ning, Y.-F. Ao, D.-X. Wang, Q.-Q. Wang, Chem. Eur. J. 2018, 24, 4268-4272.
H. Abe, D. Hashikawa, T. Minami, K. Ohtani, K. Masuda, S. Matsumoto, M. Inouye, J. Org. Chem. 2018, 83, 3132-3141;
E. V. Beletskiy, J. Schmidt, X.-B. Wang, S. R. Kass, J. Am. Chem. Soc. 2012, 134, 18534-18537;
H. Abe, Y. Aoyagi, M. Inouye, Org. Lett. 2005, 7, 59-61.
Y. Ohishi, M. Murase, H. Abe, M. Inouye, Org. Lett. 2019, 21, 6202-6207;
Y. Ohishi, N. Yamamoto, H. Abe, M. Inouye, J. Org. Chem. 2018, 83, 5766-5770;
H. Abe, C. Sato, Y. Ohishi, M. Inouye, Eur. J. Org. Chem. 2018, 3131-3138;
Y. Ohishi, H. Abe, M. Inouye, Eur. J. Org. Chem. 2017, 6975-6979;
H. Abe, T. Yoneda, Y. Ohishi, M. Inouye, Chem. Eur. J. 2016, 22, 18944-18952;
Y. Ohishi, H. Abe, M. Inouye, Chem. Eur. J. 2015, 21, 16504-16511.
For recent examples of cage molecules constructed of sp and sp2-hybridized carbons, see:
S. Cui, G. Zhuang, D. Lu, Q. Huang, H. Jia, T. Wang, S. Yang, P. Du, Angew. Chem. Int. Ed. 2018, 57, 9330-9335;
Angew. Chem. 2018, 130, 9474-9479;
J. Cremers, R. Haver, M. Rickhaus, J. O. Gong, L. Favereau, M. D. Peeks, T. D. W. Claridge, L. M. Herz, H. L. Anderson, J. Am. Chem. Soc. 2018, 140, 5352-5355;
T. Matsushima, S. Kikkawa, I. Azumaya, S. Watanabe, ChemistryOpen 2018, 7, 278-281;
X. Gu, T. Y. Gopalakrishna, H. Phan, Y. Ni, T. S. Herng, J. Sing, J. Wu, Angew. Chem. Int. Ed. 2017, 56, 15383-15387;
Angew. Chem. 2017, 129, 15585-15589;
K. Matsui, Y. Segawa, K. Itami, J. Am. Chem. Soc. 2014, 136, 16452-16458.
For reviews of shape-persistent organic cage molecules, see:
M. Mastalerz, Acc. Chem. Res. 2018, 51, 2411-2422;
G. Zhang, M. Mastalerz, Chem. Soc. Rev. 2014, 43, 1934-1947;
M. Mastalerz, Angew. Chem. Int. Ed. 2010, 49, 5042-5053;
Angew. Chem. 2010, 122, 5164-5175.
For self-association of glycosides in apolar solvents, see;
H. Abe, Y. Chida, H. Kurokawa, M. Inouye, J. Org. Chem. 2011, 76, 3366-3371;
R. P. Bonar-Law, J. K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 259-271.
For examples of solid-liquid extraction of saccharides, see:
T. Hayashi, Y. Ohishi, H. Abe, M. Inouye, J. Org. Chem. 2020, 85, 1927-1934;
M. Mazik, H. Cavga, P. G. Jones, J. Am. Chem. Soc. 2005, 127, 9045-9052;
Y.-H. Kim, J.-I. Hong, Angew. Chem. Int. Ed. 2002, 41, 2947-2950;
Angew. Chem. 2002, 114, 3071-3074;
M. Inouye, K. Takahashi, H. Nakazumi, J. Am. Chem. Soc. 1999, 121, 341-345;
A. P. Davis, R. S. Wareham, Angew. Chem. Int. Ed. 1998, 37, 2270-2273;
Angew. Chem. 1998, 110, 2397-2401.
H. Abe, H. Machiguchi, S. Matsumoto, M. Inouye, J. Org. Chem. 2008, 73, 4650-4661.
V. Ferriéres, J.-N. Bertho, D. Plusellec, Tetrahedron Lett. 1995, 36, 2749-2752.