Abstract
The polysaccharide mannan is the main surface antigen of the cell wall of Candida fungi, playing an important role in the pathogenesis of diseases caused by these mycopathogens. Mannan has a complex, comb-like structure and includes a variety of structural units, with their combination varying depending on the Candida species and strain. Glucomannan, a polysaccharide from Candida utilis, contains terminal α-d-glucose residues attached to oligomannoside side chains. This paper describes the first synthesis of a pentasaccharide structurally related to C. utilis glucomannan fragment, which is an α-(1→2)-linked tetramannoside terminated at the non-reducing end by an α-d-glucopyranosyl residue. The pentasaccharide was obtained as a 3-aminopropyl glycoside, which made it possible to synthesize also its biotinylated derivative, suitable for various glycobiological studies. The most complicated step in the pentasaccharide synthesis was stereoselective 1,2-cis-glycosylation to attach the α-d-glucopyranosyl residue. This was accomplished using a glucosyl donor specially developed in our laboratory, the protecting groups of which provide the necessary α-stereoselectivity. The target biotinylated pentasaccharide thus obtained will be used in the future as a model antigen for the detection of immunodeterminant epitopes of Candida mannans.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
P. G. Pappas, C. A. Kauffman, D. R. Andes, C. J. Clancy, K. A. Marr, L. Ostrosky-Zeichner, A. C. Reboli, M. G. Schuster, J. A. Vazquez, T. J. Walsh, T. E. Zaoutis, J. D. Sobel, Clin. Infect. Dis., 2016, 62, e1.
K. Z. Vardakas, A. Michalopoulos, K. G. Kiriakidou, E. P. Siampli, G. Samonis, M. E. Falagas, Clin. Microbiol. Infect., 2009, 15, 289.
F. Bongomin, S. Gago, R. O. Oladele, D. W. Denning, J. Fungi, 2017, 3, 57.
N. Klimko, Y. Kozlova, S. Khostelidi, O. Shadrivova, Y. Borzova, E. Burygina, N. Vasilieva, D. W. Denning, Mycoses, 2015, 58, 58.
A. Arastehfar, A. Carvalho, M. H. Nguyen, M. T. Hedayati, M. G. Netea, D. S. Perlin, M. Hoenigl, J. Fungi, 2020, 6, 211.
A. Skiada, I. Pavleas, M. Drogari-Apiranthitou, F1000Research, 2017, 6, 1917.
M. F. Mushi, A. Mmole, S. E. Mshana, BMC Res. Notes, 2019, 12, 775.
N. Shibata, H. Kobayashi, S. Suzuki, Proc. Jpn. Acad., Ser. B, 2012, 88, 250.
L. Paulovičová, E. Paulovičová, P. Farkaš, A. Čížová, P. Bystrický, V. Jančinová, J. Turánek, E. Pericolini, E. Gabrielli, A. Vecchiarelli, M. Hrubiško, FEMS Yeast Res., 2019, 19, foz009.
L. P. Erwig, N. A. Gow, Nat. Rev. Microbiol., 2016, 14, 163.
R. A. Hall, N. A. R. Gow, Mol. Microbiol., 2013, 90, 1147.
C. J. Clancy, M. H. Nguyen, J. Clin. Microbiol., 2018, 56, e01909.
W. Duettmann, C. Koidl, R. Krause, G. Lackner, A. Woelfler, M. Hoenigl, Mycoses, 2016, 59, 374.
V. B. Krylov, A. S. Solovev, I. A. Puchkin, D. V. Yashunsky, A. V. Antonets, O. Y. Kutsevalova, N. E. Nifantiev, J. Fungi, 2021, 7, 504.
N. Shibata, A. Suzuki, H. Kobayashi, Y. Okawa, Biochem. J., 2007, 404, 365.
G. Kogan, J. Sandula, V. Simkovicová, Folia Microbiol. (Praha), 1993, 38, 219.
A. Kudoh, Y. Okawa, N. Shibata, Glycobiology, 2015, 25, 74.
A. A. Karelin, Y. E. Tsvetkov, N. E. Nifantiev, Russ. Chem. Rev., 2017, 86, 1073.
V. B. Krylov, N. E. Nifantiev, Curr. Top. Microbiol. Immunol., 2020, 425, 1.
V. B. Krylov, N. E. Nifantiev, Drug Discov. Today Technol., 2020, 35–36, 35.
V. B. Krylov, A. S. Solovev, D. A. Argunov, J.-P. Latgé, N. E. Nifantiev, Heliyon, 2019, 5, e01173.
S. S. W. Wong, V. B. Krylov, D. A. Argunov, A. A. Karelin, J.-P. Bouchara, T. Fontaine, J.-P. Latgé, N. E. Nifantiev, mSphere, 2020, 5, e00688; DOI: https://doi.org/10.1128/mSphere.00688-19.
Y. E. Tsvetkov, E. A. Khatuntseva, D. V. Yashunsky, N. E. Nifantiev, Russ. Chem. Bull., 2015, 64, 990.
B. S. Komarova, S. S. W. Wong, M. V. Orekhova, Y. E. Tsvetkov, V. B. Krylov, A. Beauvais, J.-P. Bouchara, J. F. Kearney, V. Aimanianda, J.-P. Latgé, N. E. Nifantiev, J. Org. Chem., 2018, 83, 12965.
E. D. Kazakova, D. V. Yashunsky, V. B. Krylov, J.-P. Bouchara, M. Cornet, I. Valsecchi, T. Fontaine, J.-P. Latge, N. E. Nifantiev, J. Am. Chem. Soc., 2020, 142, 1175.
A. A. Karelin, Y. E. Tsvetkov, L. Paulovičová, S. Bystrick, E. Paulovičová, N. E. Nifantiev, Carbohydr. Res., 2009, 344, 29.
A. A. Karelin, Y. E. Tsvetkov, L. Paulovičová, S. Bystrick, E. Paulovičová, N. E. Nifantiev, Carbohydr. Res., 2010, 345, 1283.
D. A. Argunov, V. B. Krylov, N. E. Nifantiev, Org. Biomol. Chem., 2015, 13, 3255.
V. B. Krylov, D. A. Argunov, A. S. Solovev, M. I. Petruk, A. G. Gerbst, A. S. Dmitrenok, A. S. Shashkov, J.-P. Latgé, N. E. Nifantiev, Org. Biomol. Chem., 2018, 16, 1188.
B. S. Komarova, Y. E. Tsvetkov, N. E. Nifantiev, Chem. Rec., 2016, 16, 488.
A. I. Tokatly, D. Z. Vinnitskiy, N. E. Ustuzhanina, N. E. Nifantiev, Russ. J. Bioorg. Chem., 2021, 47, 53.
A. G. Gerbst, V. B. Krylov, N. E. Nifantiev, Carbohydrate Chemistry: Chemical and Biological Approaches, Vol. 44, Eds. A. P. Rauter, Th. K. Lindhorst, Y. Queneau, Royal Society of Chemistry, London, 2021, pp. 151–169; DOI: https://doi.org/10.1039/9781788013864-00151.
A. A. Karelin, Y. E. Tsvetkov, G. Kogan, S. Bystricky, N. E. Nifantiev, Russ. J. Bioorg. Chem., 2007, 33, 110.
F. Yamazaki, S. Sato, T. Nukada, Y. Ito, T. Ogawa, Carbohydr. Res., 1990, 201, 31.
B. S. Komarova, V. S. Dorokhova, Y. E. Tsvetkov, N. E. Nifantiev, Org. Chem. Front., 2018, 5, 909.
Y. E. Tsvetkov, M. Burg-Roderfeld, G. Loers, A. Ardá, E. V. Sukhova, E. A. Khatuntseva, A. A. Grachev, A. O. Chizhov, H.-C. Siebert, M. Schachner, N. E. Nifantiev, J. Am. Chem. Soc., 2011, 134, 426.
Y. E. Tsvetkov, O. N. Yudina, N. E. Nifantiev, Russ. Chem. Rev., 2021, 90, 171.
G. M. Lipkind, A. S. Shashkov, N. E. Nifant’ev, N. K. Kochetkov, Carbohydr. Res., 1992, 237, 11.
W. L. Armarego, Purification of Laboratory Chemicals, Butterworth-Heinemann, Amsterdam—Boston—Heidelberg—London, 2017, 8th ed., 1198 pp.
Funding
This work was financially supported by the Russian Science Foundation (Project No. 19-73-30017).
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 90th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2208–2213, November, 2021.
This paper does not contain descriptions of studies on animals or humans.
The authors declare no competing interests.
Rights and permissions
About this article
Cite this article
Yashunsky, D.V., Dorokhova, V.S., Komarova, B.S. et al. Synthesis of biotinylated pentasaccharide structurally related to a fragment of glucomannan from Candida utilis. Russ Chem Bull 70, 2208–2213 (2021). https://doi.org/10.1007/s11172-021-3334-9
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-021-3334-9