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 2015; 47(06): 836-844
DOI: 10.1055/s-0034-1379952
DOI: 10.1055/s-0034-1379952
paper
Convergent Synthesis of the Pentasaccharide Repeating Unit of the O-Antigen of Escherichia coli O36
Further Information
Publication History
Received: 10 September 2014
Accepted after revision: 02 December 2014
Publication Date:
22 December 2014 (online)
Abstract
An efficient synthesis of the pentasaccharide repeating unit of the O-antigen of Escherichia coli O36 is reported. A stereoselective [2 + 3] block glycosylation method has been exploited to obtain the target pentasaccharide derivative using thioglycoside, trichloroacetimidate, and halide-exchange glycosylation procedures. The 2-azidoethyl group has been used as the anomeric protecting group to make the glycone moiety with a readily available linker for its conjugation to a protein without destroying the cyclic structure at the reducing end. Yields were high in all the intermediate steps.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379952. Included are copies of 1D and 2D NMR spectra of compounds 1, 4, 5, 7, 8, 9, 13, 15, 16, 17, 18, 20.
- Supporting Information
-
References
- 1 Johnson JR, Russo TA. J. Lab. Clin. Med. 2002; 139: 155
- 2 Johnson JR. Clin. Microbiol. Rev. 1991; 4: 80
- 3 Robbins JB, McCracken GH, Gotschlich EC, Orskov F, Orskov I, Hanson LA. N. Engl. J. Med. 1974; 290: 1216
- 4 Besser RE, Lett SM, Weber JT, Doyle MP, Barrett TJ, Wells JG, Griffin PM. JAMA J. Am. Med. Assoc. 1993; 269: 2217
- 5a Jann B, Jann K. Curr. Top. Microbiol. Immunol. 1990; 150: 19
- 5b Ørskov F, Ørskov I. Can. J. Microbiol. 1992; 38: 699
- 6 Johnson JR, Gajewski A, Lesse AJ, Russo TA. J. Clin. Microbiol. 2003; 41: 5798
- 7a Nataro JP, Kaper JB. Clin. Microbiol. Rev. 1998; 11: 142
- 7b Panchadhayee R, Misra AK. Tetrahedron: Asymmetry 2010; 21: 2142
- 8 Perepelov AV, Wang Q, Levina EA, Ovchinnikova OG, Qian Y, Shashkov AS, Wang L, Knirel YA. Carbohydr. Res. 2014; 390: 46
- 9a Cheville NF, Arp LH. J. Am. Vet. Med. Assoc. 1978; 173: 584
- 9b Monroy MA, Knobl T, Bottino JA, Ferreira CS, Ferreira AJ. Comp. Immunol. Microbiol. Infect. Dis. 2005; 28: 1
- 10a Edwards NJ, Monteiro MA, Faller G, Walsh EJ, Moran AP, Roberts IS, High N. J. Mol. Microbiol. 2000; 35: 1530
- 10b Kukkonen M, Suomalainen M, Kyllönen P, Lähteenmäki K, Lang H, Virkolka R, Helander IM, Holst O, Korhinen TK. Mol. Microbiol. 2004; 51: 215
- 11a Roy R. Drug Discovery Today: Technol. 2004; 1: 327
- 11b Astronomo RD, Burton DR. Nat. Rev. Drug Discovery 2010; 9: 308
- 11c Guo Z, Boons G.-J. Carbohydrate-Based Vaccines and Immunotherapies . 4th ed. John Wiley; Hoboken: 2009: 416
- 12a Mandal PK, Misra AK. Tetrahedron 2008; 64: 8685
- 12b Mandal PK, Branson TR, Hayes ED, Ross JF, Gavín JA, Daranas AH, Turnbull WB. Angew. Chem. Int. Ed. 2012; 51: 5143
- 12c Mandal PK, Dhara D, Misra AK. Beilstein J. Org. Chem. 2014; 10: 293
- 12d Mandal PK, Dhara D, Misra AK. Synthesis 2014; 46: 1947
- 13 Xue J, Zhu J, Marchant RE, Guo Z. Org. Lett. 2005; 7: 3753
- 14a Dejter-Juszynsakni M, Flowersc DH. M. Carbohydr. Res. 1971; 18: 219
- 14b Lemieux RU, Bundle DR, Baker DA. J. Am. Chem. Soc. 1975; 97: 4076
- 15 Vermeer HJ, vanDijk CM, Kamerling JP, Vliegenthart JF. G. Eur. J. Org. Chem. 2001; 193
- 16 Lemieux RU, Hendriks KB, Stick V, Jakes K. J. Am. Chem. Soc. 1975; 97: 4056
- 17a Douglas NL, Ley SV, Lücking U, Warriner SL. J. Chem. Soc., Perkin Trans. 1 1998; 51
- 17b Smid P, de Ruiter GA, van der Marel GA, Rombouts FM, vanBoons JH. J. Carbohydr. Chem. 1991; 10: 833
- 18a Veeneman GH, van Leeuwen SH, vanBoom JH. Tetrahedron Lett. 1990; 31: 1331
- 18b Konradsson P, Udodong UE, Fraser-Reid B. Tetrahedron Lett. 1990; 31: 4313
- 19 Zemplén G, Gerecs A, Hadácsy I. Ber. Dtsch. Chem. Ges. 1936; 69: 1827
- 20 Bouchra M, Calinaud P, Gelas J. Carbohydr. Res. 1995; 267: 227
- 21 Kihlberg JO, Leigh DA, Bundle DR. J. Org. Chem. 1990; 55: 2860
- 22 Sarkar S, Dutta S, Das G, Sen AK. Tetrahedron 2011; 67: 4118
- 23 Liptak A, Imre J, Nanasi P. Carbohydr. Res. 1981; 92: 154
- 24 Madhusudan SK, Agnihotri G, Negi DS, Misra AK. Carbohydr. Res. 2005; 340: 1373
- 25 Pearlman WM. Tetrahedron Lett. 1967; 8: 1663
- 26 Werz DB, Seeberger PH. Angew. Chem. Int. Ed. 2005; 44: 6315
- 27 Schmidt RR, Jung K.-H In Preparative Carbohydrate Chemistry . Hanessian S. Marcel Dekker; New York: 1997: 283-312
- 28a Sau A, Santra A, Misra AK. Synlett 2012; 23: 2341
- 28b Jana M, Sau A, Santra A, Misra AK. Tetrahedron: Asymmetry 2014; 25: 632
- 29 Chen L, Kong F. Tetrahedron Lett. 2003; 44: 3691
- 30 Kanie O, Crawley SC, Palcic MM, Hindsgaul O. Carbohydr. Res. 1993; 243: 139