Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2023; 55(10): 1553-1560
DOI: 10.1055/s-0042-1751419
DOI: 10.1055/s-0042-1751419
paper
Concise Synthesis of the Hexasaccharide Repeating Unit of the Capsular Polysaccharide of Klebsiella K19 Strain
S.S. thanks the University Grants Commission (UGC-MANF), India and P.S. thanks the Bose Institute for financial support. This work was supported by the Science and Engineering Research Board (SERB), New Delhi (Project No. CRG/2019/000352 dated 23.01.2020) (A.K.M.).
Abstract
A convergent [4+2] stereoselective block glycosylation strategy has been developed for the synthesis of the hexasaccharide repeating unit of the capsular polysaccharide of Klebsiella K19 strain in very good yield. The p-methoxybenzyl (PMB) group was used as a temporary alkyl protecting group, which was removed by tuning the glycosylation conditions. A thioglycoside was used as a glycosyl acceptor in an orthogonal glycosylation reaction. A late-stage TEMPO-mediated selective oxidation of a primary hydroxyl group into carboxylic acid allowed incorporation of the d-glucuronic acid moiety in the hexasaccharide. A combination of N-iodosuccinimide (NIS) and perchloric acid supported over silica (HClO4–SiO2) was used as a thiophilic promoter for the activation of thioglycosides. HClO4–SiO2 was also used as a solid acid activator for a glycosyl trichloroacetimidate derivative.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751419. Included are copies of 1D and 2D NMR spectra of compounds 1 and 7–13.
- Supporting Information
Publication History
Received: 23 November 2022
Accepted after revision: 16 January 2023
Article published online:
15 February 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Podschun R, Ullmann U. Clin. Microbiol. Rev. 1998; 11: 589
- 2a Campos MA, Vargas MA, Regueiro V, Llompart CM, Alberti S, Bengoechea JA. Infect. Immun. 2004; 72: 7107
- 2b Casadevall A, Pirofski L.-a. J. Infect. Dis. 2001; 184: 337
- 3a Paczosa MK, Mecsas J. Microbiol. Mol. Biol. Rev. 2016; 80: 629
- 3b Feldman C, Anderson R. Pneumonia 2021; 13: 5
- 4 Ku Y.-H, Chuang Y.-C, Chen C.-C, Lee M.-F, Yang Y.-C, Tang H.-J, Yu W.-L. Sci. Rep. 2017; 7: 6634
- 5a Hawser SP, Bouchillon SK, Lascols C, Hackel M, Hoban DJ, Badal RE, Woodford N, Livermore DM. Antimicrob. Agents Chemother. 2011; 55: 3917
- 5b Di Carlo P, Pantuso G, Cusimano A, D’Arpa F, Giammanco A, Gulotta G, Latteri AM, Madonia S, Salamone G, Mammina C. BMC Gastroenterol. 2011; 11: 103
- 6a Petrosillo N, Taglietti F, Granata G. J. Clin. Med. 2019; 8: 934
- 6b Nirwati H, Sinanjung K, Fahrunissa F, Wijaya F, Napitupulu S, Hati VP, Hakim MS, Meliala A, Aman AT, Nuryastuti T. BMC Proc. 2019; 13: 20
- 7a Seco BM. S, Xu F.-F, Grafmüller A, Kottari N, Pereira CL, Seeberger PH. ACS Chem. Biol. 2020; 15: 2395
- 7b Perera SR, Sokaribo AS, White AP. Polysaccharides 2021; 2: 691
- 7c Opoku-Temeng C, Kobayashi SD, Deleo FR. Comput. Struct. Biotechnol. J. 2019; 17: 1360
- 7d Morais V, Dee V, Suárez N. Front. Bioeng. Biotechnol. 2018; 6: 145
- 7e Cress BF, Englaender JA, He W, Kasper D, Linhardt RJ, Koffas MA. G. FEMS Microbiol. Rev. 2014; 38: 660
- 8 Beurret M, Vignon M, Joseleau J.-P. Carbohydr. Res. 1986; 157: 13
- 9a Adamo R. Glycoconjugate J. 2021; 38: 397
- 9b Kay E, Cuccui J, Wren BW. npj Vaccines 2019; 4: 16
- 9c Adamo R. Acc. Chem. Res. 2017; 50: 1270
- 9d Colombo C, Pitirollo O, Lay L. Molecules 2018; 23: 1712
- 9e Mettu R, Chen C.-Y, Wu C.-Y. J. Biomed. Sci. 2020; 27: 9
- 9f Chen WH, Kotloff KL. Clin. Vaccine Immunol. 2016; 23: 904
- 9g Carbohydrates in Drug Discovery and Development. Tiwari VK. Elsevier; Amsterdam: 2020
- 10a Dhara D, Baliban SM, Huo CX, Rashidijahanabad Z, Sears KT, Nick ST, Misra AK, Tennant SM, Huang X. Chem. Eur. J. 2020; 26: 15953
- 10b Huo C.-X, Dhara D, Baliban SM, Nick ST, Tan Z, Simon S, Misra AK, Huang X. Chem. Commun. 2019; 55: 4519
- 10c Shit P, Guchhait A, Misra AK. Tetrahedron 2019; 75: 130697
- 11a Prestegard JH, Liu J, Widmalm G. Oligosaccharides and Polysaccharides . In Essentials of Glycobiology, 3rd ed. Varki A, Cummings RD, Esko JD, Stanley P, Hart GW, Aebi M, Darvill AG, Kinoshita T, Packer NH, Prestegard JH, Schnaar RL, Seeberger PH. Cold Spring Harbor Laboratory Press; Cold Spring Harbor: 2017
- 11b Foxman B. Nat. Rev. Urol. 2010; 7: 653
- 12 Tamborrini M, Werz DB, Frey J, Pluschke G, Seeberger PH. Angew. Chem. Int. Ed. 2006; 45: 6581
- 13 Ghosh S, Misra AK. Tetrahedron: Asymmetry 2010; 21: 725
- 14 Dhara D, Mandal PK, Misra AK. Tetrahedron: Asymmetry 2014; 25: 263
- 15 Guchhait G, Misra AK. Tetrahedron: Asymmetry 2009; 20: 1791
- 16 Lu X.-A, Chou C.-H, Wang C.-C, Hung S.-C. Synlett 2003; 1364
- 17 Jana M, Sau A, Misra AK. Tetrahedron: Asymmetry 2014; 25: 632
- 18 Bhattacharyya S, Magnusson BG, Wellmar U, Nilsson UJ. J. Chem. Soc., Perkin Trans. 1 2001; 886
- 19 Kanie O, Ito Y, Ogawa T. J. Am. Chem. Soc. 1994; 116: 12073
- 20 van den Bos LJ, Litjens R, van den Berg R, Overkleeft HS, van der Marel GA. Org. Lett. 2005; 7: 2007
- 21a Chakraborti AK, Gulhane R. Chem. Commun. 2003; 1896
- 21b Chakraborti AK, Chankeshwara SV. Org. Biomol. Chem. 2006; 4: 2769
- 22 Mukhopadhyay B, Maurer S, Rudolph N, van Well RM. J. Org. Chem. 2005; 70: 9059
- 24 Chen J, Feng L, Prestwich GD. J. Org. Chem. 1998; 63: 6511
- 25 Madhusudan SK, Agnihotri G, Negi DS, Misra AK. Carbohydr. Res. 2005; 340: 1373
- 26 Oikawa Y, Yoshioka T, Yonemitsu O. Tetrahedron Lett. 1982; 23: 885
- 27 Pearlman WM. Tetrahedron Lett. 1967; 8: 1663