The Journal of Organic Chemistry
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(c = 0.94, MeOH). 1H NMR (400 MHz, MeOD): δ 7.21-7.16 (m,
6.
Arbués, A.; Malaga, W.; Constant, P.; Guilhot, C.;
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Prandi, J.; Astarie-Dequeker, C., Trisaccharides of Phenolic
Glycolipids Confer Advantages to Pathogenic Mycobacteria
through Manipulation of Host-Cell Pattern-Recognition
Receptors. ACS Chem. Biol. 2016, 11 (10), 2865-2875.
2H), 7.03-6.98 (m, 2H), 5.54 (d, 1H, J = 1.5 Hz), 5.12 (d, 1H, J =
1.5 Hz), 4.57 (d, 1H, J = 7.8 Hz), 4.54-4.49 (m, 1H), 4.34-4.29 (m,
1H), 4.25 (dd, 1H, J = 2.5 Hz, J = 2.0 Hz), 3.65 (s, 3H), 3.82-3.59
(m, 9H), 3.58 (s, 3H), 3.50 (s, 3H), 3.49 (s, 3H), 3.54-3.47 (m, 1H),
3.45-3.36 (m, 3H), 3.40 (s, 3H), 3.26-3.18 (m, 2H), 3.10 (d, 1H, J
= 8.5 Hz, J = 8.5 Hz), 2.99-2.93 (m, 1H), 2.78 (t, 2H, J = 7.0 Hz),
2.76-2.70 (m, 1H), 2.18 (t, 2H, J = 7.2 Hz), 1.79-1.54 (m, 4H), 1.46-
1.38 (m, 2H), 1.27 (d, 3H, J = 6.0 Hz), 1.24 (d, 3H, J = 6.0 Hz).
13C{1H} NMR (100 MHz, MeOD): δ 174.6, 154.9, 133.2, 129.6,
116.2, 103.5, 99.0, 97.4, 80.7, 80.5, 77.8, 76.3, 75.3, 74.6, 74.0,
71.9, 71.6, 69.8, 69.3, 67.8, 61.9, 60.2, 59.5, 58.4, 57.7, 57.1, 56.1,
55.6, 40.5, 39.7, 35.4, 34.2, 28.3, 28.1, 25.5, 16.9, 16.7. HRMS
(ESI) m/z: [M + H]+ Calcd for C41H66N3O16S 888.4164; Found
888.4167.
7.
Tabouret, G.; Astarie-Dequeker, C.; Demangel, C.;
Malaga, W.; Constant, P.; Ray, A.; Honoré, N.; Bello, N. F.;
Perez, E.; Daffé, M.; Guilhot, C., Mycobacterium leprae
Phenolglycolipid-1 Expressed by Engineered M. bovis BCG
Modulates Early Interaction with Human Phagocytes. PLoS
Pathog. 2010, 6 (10), e1001159.
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Yu, B.; Sun, J.; Yang, X., Assembly of Naturally
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Occurring Glycosides, Evolved Tactics, and Glycosylation
Methods. Accounts Chem. Res. 2012, 45 (8), 1227-1236.
9.
Liptak, A.; Borbas, A.; Bajza, I., Synthesis of
Carbohydrate-Containing Surface Antigens of Mycobacteria.
Med. Res. Rev. 1994, 14 (3), 307-352.
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Fujiwara, T.; Hunter, S. W.; Cho, S. N.; Aspinall, G. O.;
Brennan, P. J., Chemical synthesis and serology of disaccharides
and trisaccharides of phenolic glycolipid antigens from the
leprosy bacillus and preparation of a disaccharide protein
conjugate for serodiagnosis of leprosy. Infect.Immun. 1984, 43
(1), 245-252.
11.
Fujiwara, T.; Aspinall, G. O.; Hunter, S. W.; Brennan,
AUTHOR INFORMATION
Corresponding Author
Dr. Jin Wang, wangj01@yctu.edu.cn
ORCID
P. J., Chemical synthesis of the trisaccharide unit of the species-
specific phenolic glycolipid from Mycobacterium leprae.
Carbohyd. Res. 1987, 163 (1), 41-52.
12.
Borbás, A.; Lipták, A., A new approach to the chemical
synthesis of the trisaccharide, and the terminal di- and mono-
saccharide units of the major, serologically active glycoplipid
from Mycobacterium leprae. Carbohyd. Res. 1993, 241 (0), 99-
116.
Jin Wang : 0000-0002-2929-6381
ACKNOWLEDGMENT
13.
Elsaidi, H. R. H.; Barreda, D. R.; Cairo, C. W.; Lowary,
We thank the National Natural Science Foundation of China
(No.81903427), the Jiangsu key Research and Development plan
(Social Development No.BE2020672) project, the Natural Science
Foundation of Jiangsu Province (BK20160443), the Six Talent
Peaks Project in Jiangsu Province (SWYY-094) for financial
support. We also thank Dr. David Huang (Yale University) for
proofreading this manuscript.
T. L., Mycobacterial Phenolic Glycolipids with a Simplified Lipid
Aglycone Modulate Cytokine Levels through Toll-Like Receptor
2. ChemBioChem 2013, 14 (16), 2153-2159.
14.
Lowary, T. L., Twenty Years of Mycobacterial Glycans:
Furanosides and Beyond. Accounts Chem. Res. 2016, 49 (7),
1379-1388.
15.
Porcelli, L.; Gilardi, F.; Laghezza, A.; Piemontese, L.;
Mitro, N.; Azzariti, A.; Altieri, F.; Cervoni, L.; Fracchiolla, G.;
Giudici, M.; Guerrini, U.; Lavecchia, A.; Montanari, R.; Di
Giovanni, C.; Paradiso, A.; Pochetti, G.; Simone, G. M.;
Tortorella, P.; Crestani, M.; Loiodice, F., Synthesis,
Characterization and Biological Evaluation of Ureidofibrate-Like
Derivatives Endowed with Peroxisome Proliferator-Activated
Receptor Activity. J.Med. Chem. 2011, 55 (1), 37-54.
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