Orthogonal Glycosylation with Phosphate Acceptors for Expeditious Synthesis of Bacterial Inner Core Oligosaccharides.

Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 101294643 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1861-471X (Electronic) Linking ISSN: 1861471X NLM ISO Abbreviation: Chem Asian J Subsets: MEDLINE

Original Publication: Weinheim, Germany : Wiley-VCH, c2006-

Phosphates* ; Oligosaccharides*/chemistry; Glycosylation ; Lipopolysaccharides/chemistry ; Disaccharides

We report a practical one-pot glycosylation strategy for synthesis of bacterial inner core oligosaccharides that composed of unavailable L-glycero-D-manno and D-glycero-D-manno-heptopyranose components. The glycosylation method features a new orthogonal glycosylation procedure; whereby a phosphate acceptor is coupled with a thioglycosyl donor producing a disaccharide phosphate, which can be engaged in another orthogonal glycosylation procedure to couple with a thioglycosyl acceptor. The phosphate acceptors used in above one-pot procedure are directly prepared from thioglycosyl acceptors via the in-situ phosphorylation. Such phosphate acceptor preparation protocol eliminates the traditional protection and deprotection procedures. Based on the new one-pot glycosylation strategy, two partial inner core structures of Yersinia pestis lipopolysaccharide and Haemophilus ducreyi lipooligosaccharide were acquired.
(© 2023 Wiley-VCH GmbH.)

B. Yu, Acc. Chem. Res. 2018, 51, 507-516 and references cited therein.
J. Ling, C. S. Bennett, Asian J. Org. Chem. 2019, 8, 802-813 and references cited therein.
A. J. Fairbanks, S. L. Flitsch, M. C. Galan, Org. Biomol. Chem. 2020, 18, 6979-6982 and references cited therein.
G. A. Bradshaw, A. C. Colgan, N. P. Allen, I. Pongener, M. B. Boland, Y. Ortin, E. M. McGarrigle, Chem. Sci. 2019, 10, 508.
P. Li, H. He, Y. Zhang, R. Yang, L. Xu, Z. Chen, Y. Huang, L. Bao, G. Xiao, Nat. Commun. 2020, 11, 405.
F. Yu, J. Li, P. M. DeMent, Y.-J. Tu, H. B. Schlegel, H. M. Nguyen, Angew. Chem. Int. Ed. 2019, 58, 6957-6961.
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.
Review in oligosaccharide synthesis: S. S. Kulkarni, C.-C. Wang, N. M. Sabbavarapu, A. R. Podilapu, P.-H. Liao, S.-C. Hung, Chem. Rev. 2018, 118, 8025-8104.
Review in oligosaccharide synthesis: M. Panza, S. G. Pistorio, K. J. Stine, A. V. Demchenko, Chem. Rev. 2018, 118, 8105-8150.
Review in oligosaccharide synthesis: M. M. Nielsen, C. M. Pedersen, Chem. Rev. 2018, 118, 8285-8358.
Review in oligosaccharides: L. Wen, G. Edmunds, C. Gibbons, J. Zhang, M. R. Gadi, H. Zhu, J. Fang, X. Liu, Y. Kong, P. Wang, Chem. Rev. 2018, 118, 8151-8187.
Y. Zhang, G. Xiang, S. He, Y. Hu, Y. Liu, L. Xu, G. Xiao, Org. Lett. 2019, 21, 2335-2339.
S. Dey, H.-J. Lo, C.-H. Wong, J. Am. Chem. Soc. 2019, 141, 10309-10314.
F. Yoshida, H. Yoshinaka, H. Tanaka, S. Hanashima, Y. Yamaguchi, M. Ishihara, M. Saburomaru, Y. Kato, R. Saito, H. Ando, M. Kiso, A. Imamura, H. Ishida, Chem. Eur. J. 2019, 25, 796-805.
K. N. Baryal, S. Ramadan, G. Su, C. Huo, Y. Zhao, J. Liu, L. C. Hsieh-Wilson, X. Huang, Angew. Chem. Int. Ed. 2023, 62, e202211985.
G. Tian, J. Hu, C. Qin, L. Li, X. Zou, J. Cai, P. H. Seeberger, J. Yin, Angew. Chem. Int. Ed. 2020, 59, 13362-13370.
X.-Y. Zhou, L.-X. Li, Z. Zhang, S.-C. Duan, Y.-W. Huang, Y.-Y. Luo, X.-D. Mu, Z.-W. Chen, Y. Qin, J. Hu, J. Yin, J.-S. Yang, Angew. Chem. Int. Ed. 2022, 61, e202204420.
 .
Y. Wu, D.-C. Xiong, S.-C. Chen, Y.-S. Wang, X.-S. Ye, Nat. Commun. 2017, 8, 14851;.
W. Yao, D.-C. Xiong, Y. Yang, C. Geng, Z. Cong, F. Li, B.-H. Li, X. Qin, L.-N. Wang, W.-Y. Xue, N. Yu, H. Zhang, X. Wu, M. Liu, X.-S. Ye, Nat. Synth. 2022, 1, 854-863.
A. A. Joseph, A. Pardo-Vargas, P. H. Seeberger, J. Am. Chem. Soc. 2020, 142, 8561-8564.
E. Segerstedt, K. Mannerstedt, M. Johansson, S. Oscarson, J. Carbohydr. Chem. 2004, 23, 443-452.
T. Ohara, A. Adibekian, D. Esposito, P. Stallforth, P. H. Seeberger, Chem. Commun. 2010, 46, 4106-4108.
K. Mannerstedt, E. Segerstedt, J. Olsson, S. Oscarson, Org. Biomol. Chem. 2008, 6, 1087-1091.
Y. Yang, C. E. Martinab, P. H. Seeberger, Chem. Sci. 2012, 3, 896.
Y. Yang, S. Oishi, C. E. Martin, P. H. Seeberger, J. Am. Chem. Soc. 2013, 135, 6262-6271.
C. Stanetty, M. Walter, P. Kosma, J. Org. Chem. 2014, 79, 582-598.
P. Kosma, Curr. Org. Chem. 2008, 12, 1021-1039.
S. K. Mulani, K.-C. Cheng, K.-K. T. Mong, Org. Lett. 2015, 17, 5536-5539.
M. Durka, K. Buffet, T. Li, A. Tikad, B. Hagen, S. P. Vincent, Carbohydr. Chem.: Proven Synthetic Methods 2014, 2, 77-83.
T. K. Pradhan, C.-C. Lin, K.-K. T. Mong, Synlett 2013, 24, 219-222.
Reference for compound 1: K.-K. T. Mong, K.-C. Cheng, I-. Lu, C.-W. Pan, Y.-F. Wang, L−C. Shen, J. Org. Chem. 2020, 85(24), 16060-16071.
O. J. Plante, E. R. Palmacci, R. B. Andrade, P. H. Seeberger, J. Am. Chem. Soc. 2001, 123, 9545-9554.
R. D. Perry, J. D. Fetherston, Clin. Microbiol. Rev. 1997, 10, 35-66. (Plague).
D. A. Lewis, O. Mitjà, Curr. Opin. Infect. Dis. 2016, 29, 52-57.
E. K. Schweda, J. A. Jonasson, P. E. Jansson, J. Bacteriol. 1995, 177, 5316-5321.
C. Bernlind, S. Bennett, S. Oscarson, Tetrahedron: Asymmetry 2000, 11, 481-492.
S. Luo, Y. Liu, T. Hao, W. Ma, Y. Luo, S. Wang, Z. Xu, C. Hu, L. Wen, T. Li, Org. Lett. 2023, 25, 2312-2317.
Reference for s1 in SI, 3, 4, and 21: Y. H. Lin, B. Ghosh, K.-K. T. Mong, Chem. Commun. 2012, 48, 10910-10912.
A. J. Mancuso, D. S. Brownfain, D. Swern, J. Org. Chem. 1979, 44, 4148-4150.
Reference for N−O cleavage: D. B. Ramachary, C. F. Barbas, Org. Lett. 2005, 7, 1577-15780.
D. Lloyd, M. Bylsma, D. K. Bright, X. Chen, C. S. Bennett, J. Org. Chem. 2017, 82, 3926-3934.
Reference for 22: H. D. Premathilake, L. K. Mydock, A. V. Demchenko, J. Org. Chem. 2010, 75, 1095-1100.
Reference for thiogalactoside 23: C. Wang, H. Wang, X. Huang, L.-H. Zhang, X.-S. Ye, Synlett 2006, 2846-2850.
Reference for compounds s6 in SI and 27: H. B. Boren, K. Eklind, P. J. Garegg, B. Lindberg, A. Pilotti, Acta Chem. Scand. 1972, 26, 4143-4146.
Y. A. Knirel, A. P. Anisimov, Acta. Naturae 2012, 4, 46-58.
A. A. Hettikankanamalage, R. Lassfolk, F. S. Ekholm, R. Leino, D. Crich, Chem. Rev. 2020, 120, 7104-7151 and references cited therein.
Reference for compound 35 and reductive etherification: C.-W. Chen, C.-C. Wang, X.-R. Li, H. Witek, K.-K. T. Mong, Org. Biomol. Chem. 2020, 18, 3135-3141.
Reference for compound 36: C.-C. Wang, S. S. Kulkarni, J.-C. Lee, S.-Y. Luo, S.-C. Hung, Nat. Protoc. 2008, 3, 97-113.
Preparation of compound 38 was given in scheme s2 on the supporting information.
Reference for compound s2 in SI: R. Kowalczyk, P. W. R. Harris, M. A. Brimble, R. P. Dunbar, Synthesi 2009, 13, 2210-2222.
Reference for compound s8 in SI: S. Traboni, E. Bedini, M. Giordano, A Iadonisi, Tetrahedron Lett. 2019, 60, 1777-1780.

111-2113-M-A49-029 National Science and Technology council (Taiwan)

Keywords: Inner core oligosaccharides; Orthogonal glycosylation; Phosphate acceptors; Phosphorylation; one-pot glycosylation

0 (Phosphates)
0 (Oligosaccharides)
0 (Lipopolysaccharides)
0 (Disaccharides)

Date Created: 20230620 Date Completed: 20231023 Latest Revision: 20231023

20231215

10.1002/asia.202300424

37339944