Chemical Synthesis of Sialyl N-Glycans and Analysis of Their Recognition by Neuraminidase.
N-glycans
deuterium labeling
glycosylation
neuraminidase
sialic acids
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
08 11 2021
08 11 2021
Historique:
received:
16
08
2021
pubmed:
15
9
2021
medline:
15
12
2021
entrez:
14
9
2021
Statut:
ppublish
Résumé
The chemical synthesis of a fully sialylated tetraantennary N-glycan has been achieved for the first time by using the diacetyl strategy, in which NHAc is protected as NAc
Identifiants
pubmed: 34520098
doi: 10.1002/anie.202111035
doi:
Substances chimiques
Polysaccharides
0
Sialic Acids
0
Deuterium
AR09D82C7G
Neuraminidase
EC 3.2.1.18
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
24686-24693Subventions
Organisme : Japan Society for the Promotion of Science
ID : 15H05836
Organisme : Japan Society for the Promotion of Science
ID : 16H05924
Organisme : Japan Society for the Promotion of Science
ID : 20H00404
Organisme : Japan Society for the Promotion of Science
ID : 20H05675
Organisme : Japan Society for the Promotion of Science
ID : 20K05727
Organisme : Japan Society for the Promotion of Science
ID : 16H01885
Organisme : Japan Society for the Promotion of Science
ID : 20H04709
Organisme : Japan Society for the Promotion of Science
ID : 21H05074
Organisme : Core Research for Evolutional Science and Technology
ID : JPMJCR20R3
Organisme : Japan Agency for Medical Research and Development
ID : 20ek0109444h0001
Organisme : Japan Agency for Medical Research and Development
ID : 21ek0109444h0002
Organisme : Japan Agency for Medical Research and Development
ID : 20fk0210079h0001
Organisme : PRIN 2017
ID : 2017XZ2ZBK
Organisme : European Research Council (ERC)
ID : 851356
Informations de copyright
© 2021 Wiley-VCH GmbH.
Références
M. M. Fuster, J. D. Esko, Nat. Rev. Cancer 2005, 5, 526-542;
Y. van Kooyk, G. A. Rabinovich, Nat. Immunol. 2008, 9, 593-601;
R. G. Lichtenstein, G. A. Rabinovich, Cell Death Differ. 2013, 20, 976-986.
Y. Takeda, K. Totani, I. Matsuo, Y. Ito, Curr. Opin. Chem. Biol. 2009, 13, 582-591.
J. F. Cipollo, A. M. Awad, C. E. Costello, C. B. Hirschberg, J. Biol. Chem. 2005, 280, 26063-26072.
J. D. Marth, P. K. Grewal, Nat. Rev. Immunol. 2008, 8, 874-887;
E. Maverakis, K. Kim, M. Shimoda, M. E. Gershwin, F. Patel, R. Wilken, S. Raychaudhuri, L. R. Ruhaak, C. B. Lebrilla, J. Autoimmune 2015, 57, 1-13.
J. W. Dennis, M. Granovsky, C. E. Warren, Biochim. Biophys. Acta Gen. Subj. 1999, 1473, 21-34.
J. J. Skehel, D. C. Wiley, Annu. Rev. Biochem. 2000, 69, 531-569;
M. N. Matrosovich, T. Y. Matrosovich, T. Gray, N. A. Roberts, H.-D. Klenk, J. Virol. 2004, 78, 12665-12667.
P. R. Crocker, J. C. Paulson, A. Varki, Nat. Rev. Immunol. 2007, 7, 255-266;
M. S. Macauley, P. R. Crocker, J. C. Paulson, Nat. Rev. Immunol. 2014, 14, 653-666.
J. C. Paulson, O. Blixt, B. E. Collins, Nat. Chem. Biol. 2006, 2, 238-248;
A. Shirakawa, Y. Manabe, K. Fukase, Molecules 2021, 26, 1040.
Y. Kajihara, Y. Suzuki, N. Yamamoto, K. Sasaki, T. Sakakibara, L. R. Juneja, Chem. Eur. J. 2004, 10, 971-985.
B. Wu, Z. Hua, J. D. Warren, K. Ranganathan, Q. Wan, G. Chen, Z. Tan, J. Chen, A. Endo, S. J. Danishefsky, Tetrahedron Lett. 2006, 47, 5577-5579;
P. Wang, J. Zhu, Y. Yuan, S. J. Danishefsky, J. Am. Chem. Soc. 2009, 131, 16669-16671;
M. A. Walczak, S. J. Danishefsky, J. Am. Chem. Soc. 2012, 134, 16430-16433;
M. A. Walczak, J. Hayashida, S. J. Danishefsky, J. Am. Chem. Soc. 2013, 135, 4700-4703.
R. Schuberth, C. Unverzagt, Tetrahedron Lett. 2005, 46, 4201-4204;
S. Eller, R. Schuberth, G. Gundel, J. Seifert, C. Unverzagt, Angew. Chem. Int. Ed. 2007, 46, 4173-4175;
Angew. Chem. 2007, 119, 4251-4253;
D. Ott, J. Seifert, I. Prahl, M. Niemietz, J. Hoffman, J. Guder, M. Mönnich, C. Unverzagt, Eur. J. Org. Chem. 2012, 5054-5068;
M. Mönnich, S. Eller, T. Karagiannis, L. Perkams, T. Luber, D. Ott, M. Niemietz, J. Hoffman, J. Walcher, L. Berger, M. Pischl, M. Weishaupt, C. Wirkner, R. G. Lichtenstein, C. Unverzagt, Angew. Chem. Int. Ed. 2016, 55, 10487-10492;
Angew. Chem. 2016, 128, 10643-10648;
T. Luber, M. Niemietz, T. Karagiannis, M. Mönnich, D. Ott, L. Perkams, J. Walcher, L. Berger, M. Pischl, M. Weishaupt, S. Eller, J. Hoffman, C. Unverzagt, Angew. Chem. Int. Ed. 2018, 57, 14543-14549;
Angew. Chem. 2018, 130, 14751-14757.
M. Hagiwara, M. Dohi, Y. Nakahara, K. Komatsu, Y. Asahina, A. Ueki, H. Hojo, Y. Nakahara, Y. Ito, J. Org. Chem. 2011, 76, 5229-5239;
S. Hanashima, S. Manabe, Y. Ito, Angew. Chem. Int. Ed. 2005, 44, 4218-4224;
Angew. Chem. 2005, 117, 4290-4296;
I. Matsuo, M. Wada, S. Manabe, Y. Yamaguchi, K. Otake, K. Kato, Y. Ito, J. Am. Chem. Soc. 2003, 125, 3402-3403;
J. Seifert, M. Lergenmüller, Y. Ito, Angew. Chem. Int. Ed. 2000, 39, 531-534;
Angew. Chem. 2000, 112, 541-544.
M. V. Chiesa, R. R. Schmidt, Eur. J. Org. Chem. 2000, 3541-3554.
M. Nagasaki, Y. Manabe, N. Minamoto, K. Tanaka, A. Silipo, A. Molinaro, K. Fukase, J. Org. Chem. 2016, 81, 10600-10616;
Y. Manabe, H. Shomura, N. Minamoto, M. Nagasaki, Y. Takakura, K. Tanaka, A. Silipo, A. Molinaro, K. Fukase, Chem. Asian J. 2018, 13, 1544-1551.
N. Komura, K. Kato, T. Udagawa, S. Asano, H.-N. Tanaka, A. Imamura, H. Ishida, M. Kiso, H. Ando, Science 2019, 364, 677-680.
R. Schauer, Angew. Chem. Int. Ed. Engl. 1973, 12, 127-138;
Angew. Chem. 1973, 85, 128-140.
S. S. Shivatare, S.-H. Chang, T.-I. Tsai, C.-T. Ren, H.-Y. Chuang, L. Hsu, C.-W. Lin, S.-T. Li, C.-Y. Wu, C.-H. Wong, J. Am. Chem. Soc. 2013, 135, 15382-15391;
C. Gao, M. S. Hanes, L. A. Byrd-Leotis, M. Wei, N. Jia, R. J. Kardish, T. R. McKitrick, D. A. Steinhauer, R. D. Cummings, Cell Chem. Biol. 2019, 26, 535-547.e534;
A. Koizumi, I. Matsuo, M. Takatani, A. Seko, M. Hachisu, Y. Takeda, Y. Ito, Angew. Chem. Int. Ed. 2013, 52, 7426-7431;
Angew. Chem. 2013, 125, 7574-7579;
Z. Wang, Z. S. Chinoy, S. G. Ambre, W. Peng, R. McBride, R. P. de Vries, J. Glushka, J. C. Paulson, G.-J. Boons, Science 2013, 341, 379-383;
L. Li, Y. Liu, C. Ma, J. Qu, A. D. Calderon, B. Wu, N. Wei, X. Wang, Y. Guo, Z. Xiao, J. Song, G. Sugiarto, Y. Li, H. Yu, X. Chen, P. G. Wang, Chem. Sci. 2015, 6, 5652-5661;
T. Li, M. Huang, L. Liu, S. Wang, K. W. Moremen, G.-J. Boons, Chem. Eur. J. 2016, 22, 18742-18746;
I. A. Gagarinov, T. Li, J. S. Toraño, T. Caval, A. D. Srivastava, J. A. W. Kruijtzer, A. J. R. Heck, G.-J. Boons, J. Am. Chem. Soc. 2017, 139, 1011-1018;
T. Li, L. Liu, N. Wei, J.-Y. Yang, D. G. Chapla, K. W. Moremen, G.-J. Boons, Nat. Chem. 2019, 11, 229-236;
L. Liu, A. R. Prudden, C. J. Capicciotti, G. P. Bosman, J.-Y. Yang, D. G. Chapla, K. W. Moremen, G.-J. Boons, Nat. Chem. 2019, 11, 161-169;
Q. Chao, Y. Ding, Z.-H. Chen, M.-H. Xiang, N. Wang, X.-D. Gao, Front. Chem. 2020, 8, 00513;
S. S. Shivatare, S.-H. Chang, T.-I. Tsai, S. Y. Tseng, V. S. Shivatare, Y.-S. Lin, Y.-Y. Cheng, C.-T. Ren, C.-C. D. Lee, S. Pawar, C.-S. Tsai, H.-W. Shih, Y.-F. Zeng, C.-H. Liang, P. D. Kwong, D. R. Burton, C.-Y. Wu, C.-H. Wong, Nat. Chem. 2016, 8, 338-346.
J. Y. Baek, B.-Y. Lee, M. G. Jo, K. S. Kim, J. Am. Chem. Soc. 2009, 131, 17705-17713.
J. Zhou, Y. Manabe, K. Tanaka, K. Fukase, Chem. Asian J. 2016, 11, 1436-1440;
M. Tsutsui, J. Sianturi, S. Masui, K. Tokunaga, Y. Manabe, K. Fukase, Eur. J. Org. Chem. 2020, 1802-1810.
S. T. Cohen-Anisfeld, P. T. Lansbury, J. Am. Chem. Soc. 1993, 115, 10531-10537;
T. Inazu, K. Kobayashi, Synlett 1993, 869-870;
K. J. Doores, Y. Mimura, R. A. Dwek, P. M. Rudd, T. Elliott, B. G. Davis, Chem. Commun. 2006, 1401-1403.
C. Unverzagt, H. Kunz, J. C. Paulson, J. Am. Chem. Soc. 1990, 112, 9308-9309;
N. Bézay, G. Dudziak, A. Liese, H. Kunz, Angew. Chem. Int. Ed. 2001, 40, 2292-2295;
Angew. Chem. 2001, 113, 2350-2353;
K. Baumann, D. Kowalczyk, H. Kunz, Angew. Chem. Int. Ed. 2008, 47, 3445-3449;
Angew. Chem. 2008, 120, 3494-3498.
K. Tanaka, T. Miyagawa, K. Fukase, Synlett 2009, 2009, 1571-1574;
H. Tanaka, Y. Iwata, D. Takahashi, M. Adachi, T. Takahashi, J. Am. Chem. Soc. 2005, 127, 1630-1631.
C.-S. Yu, K. Niikura, C.-C. Lin, C.-H. Wong, Angew. Chem. Int. Ed. 2001, 40, 2900-2903;
Angew. Chem. 2001, 113, 2984-2987;
K. Tanaka, Y. Fujii, H. Tokimoto, Y. Mori, S.-i. Tanaka, G.-m. Bao, E. R. O. Siwu, A. Nakayabu, K. Fukase, Chem. Asian J. 2009, 4, 574-580;
Y. Uchinashi, K. Tanaka, Y. Manabe, Y. Fujimoto, K. Fukase, J. Carbohydr. Chem. 2014, 33, 55-67.
D. Crich, S. Sun, J. Org. Chem. 1996, 61, 4506-4507;
D. Crich, S. Sun, J. Org. Chem. 1997, 62, 1198-1199;
D. Crich, S. Sun, J. Am. Chem. Soc. 1998, 120, 435-436;
S.-i. Tanaka, M. Takashina, H. Tokimoto, Y. Fujimoto, K. Tanaka, K. Fukase, Synlett 2005, 2325-2328;
K. Tanaka, Y. Mori, K. Fukase, J. Carbohydr. Chem. 2009, 28, 1-11.
M. Imoto, H. Yoshimura, N. Sakaguchi, S. Kusumoto, T. Shiba, Tetrahedron Lett. 1985, 26, 1545-1548;
M. Imoto, H. Yoshimura, T. Shimamoto, N. Sakaguchi, S. Kusumoto, T. Shiba, Bull. Chem. Soc. Jpn. 1987, 60, 2205-2214;
M. Schultz, H. Kunz, Tetrahedron Lett. 1992, 33, 5319-5322.
B. Yu, H. Tao, Tetrahedron Lett. 2001, 42, 2405-2407;
B. Yu, J. Sun, Chem. Commun. 2010, 46, 4668-4679.
M. Bartra, P. Romea, F. Urpí, J. Vilarrasa, Tetrahedron 1990, 46, 587-594.
P. D. Jeffrey, S. W. McCombie, J. Org. Chem. 1982, 47, 587-590;
H. Kunz, H. Waldmann, Angew. Chem. Int. Ed. Engl. 1984, 23, 71-72;
Angew. Chem. 1984, 96, 49-50.
S. Re, N. Miyashita, Y. Yamaguchi, Y. Sugita, Biophys. J. 2011, 101, L44-L46;
W. Nishima, N. Miyashita, Y. Yamaguchi, Y. Sugita, S. Re, J. Phys. Chem. B 2012, 116, 8504-8512.
W. Huang, D. Wang, M. Yamada, L.-X. Wang, J. Am. Chem. Soc. 2009, 131, 17963-17971;
W. Peng, R. P. de Vries, O. C. Grant, A. J. Thompson, R. McBride, B. Tsogtbaatar, P. S. Lee, N. Razi, I. A. Wilson, R. J. Woods, J. C. Paulson, Cell Host Microbe 2017, 21, 23-34;
Z. Wu, Y. Liu, L. Li, X.-F. Wan, H. Zhu, Y. Guo, M. Wei, W. Guan, P. G. Wang, Org. Biomol. Chem. 2017, 15, 8946-8951;
L. Li, W. Guan, G. Zhang, Z. Wu, H. Yu, X. Chen, P. G. Wang, Glycobiology 2020, 30, 334-345.
H.-L. Yen, C.-H. Liang, C.-Y. Wu, H. L. Forrest, A. Ferguson, K.-T. Choy, J. Jones, D. D.-Y. Wong, P. P.-H. Cheung, C.-H. Hsu, O. T. Li, K. M. Yuen, R. W. Y. Chan, L. L. M. Poon, M. C. W. Chan, J. M. Nicholls, S. Krauss, C.-H. Wong, Y. Guan, R. G. Webster, R. J. Webby, M. Peiris, Proc. Natl. Acad. Sci. USA 2011, 108, 14264-14269;
N. Tewawong, B. M. Marathe, Y. Poovorawan, S. Vongpunsawad, R. J. Webby, E. A. Govorkova, PLoS One 2018, 13, e0190877.