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 2021; 53(19): 3613-3620
DOI: 10.1055/s-0037-1610777
DOI: 10.1055/s-0037-1610777
paper
Synthesis of Pentasaccharide Repeating Unit Corresponding to the Cell Wall O-Polysaccharide of Salmonella enterica O55 Strain Containing a Rare Sugar 3-Acetamido-3-deoxy-d-fucose
A.G. and M.K. thank Council of Scientific and Industrial Research, New Delhi, India (CSIR) for providing senior research fellowships. This work was supported by Science and Engineering Research Board (SERB), New Delhi (Project No. CRG/2019/000352 dated 23.01.2020) (A.K.M.).
Abstract
A pentasaccharide repeating unit corresponding to the cell wall O-antigen of Salmonella enterica O55 containing a rare sugar, 3-acetamido-3-deoxy-d-fucose has been synthesized as its p-methoxyphenyl glycoside using a sequential stereoselective glycosylation strategy. A suitably functionalized 3-azido-3-deoxy-d-fucose thioglycoside derivative was prepared in very good yield and used in the stereoselective glycosylation reaction. Functionalized monosaccharide intermediates were prepared judiciously and stereoselectively assembled to get the desired pentasaccharide derivative in excellent yield.
Key words
pentasaccharide - glycosylation - 3-acetamido-3-deoxy-d-fucose - Salmonella enterica - stereoselectiveSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610777. Copies of 1D and 2D NMR spectra of compounds 1 and 8–17 are provided.
- Supporting Information
Publication History
Received: 24 April 2021
Accepted after revision: 31 May 2021
Article published online:
24 June 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Mandeville KL, Krabshuis J, Ladep NG, Mulder CJ. J, Quigley EM. M, Khan SA. World J. Gastroenterol. 2009; 15: 2839
- 1b Milivojevic V, Milosavljevic T. Curr. Treat. Options Gastroenterol. 2020; 18: 148
- 1c Dumic I, Nordin T, Jecmenica M, Lalosevic MS, Milosavljevic T, Milovanovic T. Can. J. Gastroenterol. Hepatol. 2019; 2019: 6757524 , DOI: 10.1155/2019/6757524
- 2a Fletcher SM, Mclaws M.-L, Ellis JT. J. Public Health Res. 2013; 2: 42
- 2b Williams J, Roberts S, Ali F, Cheung W, Cohen D, Demery G, Edwards A, Greer M, Hellier M, Hutchings H, Ip B, Longo M, Russell I, Snooks H, Williams J. Gut 2007; 56 (Suppl. 01) : 1
- 2c Guerrant RL, Hughes JM, Lima NL, Crane J. Rev. Infect. Dis. 1990; 12: S41
- 3a Oloruntoba EO, Folarin TB, Idowu-Ayede A. Afr. Health Sci. 2014; 14: 1001
- 3b Huttly SR, Morris SS, Pisani V. Bull. W. H. O. 1997; 75: 163
- 3c Florez ID, Niño-Serna LF, Beltrá-Arroyave CP. Curr. Infect. Dis. Rep. 2020; 22: 4
- 4a Casburnn-Jones AC, Farthing MJ. G. Gut 2004; 53: 296
- 4b Lima AA, Guerrant RL. Epidemiol. Rev. 1992; 14: 222
- 4c Niyogi SK, Saha MR, De SP. Indian J. Public Health 1994; 38: 29
- 4d Shankar P, Mishra J, Bharti V, Parashar D, Singh S. J. Lab. Physicians 2019; 11: 275
- 5a Beatty ME, Adcock PM, Smith SW, Quinlan K, Kamimoto LA, Rowe SY, Scott K, Conover C, Varchmin T, Bopp CA, Greene KD, Bibb B, Slutsker L, Mintz ED. Clin. Infect. Dis. 2006; 42: 329
- 5b Gomes TA. T, Elias WP, Scaletsky IC. A, Guth BE. C, Rodrigues JF, Piazza RM. F, Ferreira LC. S, Martinez MB. Braz. J. Microbiol. 2016; 47: 3
- 6 Baker S, The HC. Curr. Opin. Infect. Dis. 2018; 31: 449
- 7 Davies HG, Bowman C, Luby SP. J. Infect. 2017; 74 (Suppl. 01) : S66
- 8 Hamilton AL, Kamm MA, Ng SC, Morrison M. Clin. Microbiol. Rev. 2018; 31: e00085
- 9a Aljoudi AS, Al-Mazam A, Choudhry AJ. J. Family Community Med. 2010; 17: 29
- 9b Lu X, Zeng M, Xu J, Zhou H, Gu B, Li Z, Jin H, Wang X, Zhang W, Hu Y, Xiao W, Zhu B, Xu X, Kan B. EbioMedicine 2019; 42: 133
- 10a Crum-Cianflone NF. Curr. Gastroenterol. Rep. 2008; 10: 424
- 10b Zha L, Garrett S, Sun J. Diseases 2019; 7: 28
- 11a Stoycheva MV, Murdjeva MA. Folia Med. (Sofia, Bulg.) 2006; 48: 5
- 11b Ray KA, Warnick LD, Mitchell RM, Kaneene JB, Ruegg PL, Wells SJ, Fossler CP, Halberd LW, May K. J. Dairy Sci. 2006; 89: 2038
- 11c Mu H, Bai H, Sun F, Liu Y, Lu C, Qiu Y, Chen P, Yang Y, Kong L, Duan J. Nat. Commun. 2019; 10: 4039
- 11d Hirose K, Tamura K, Sagara H, Watanabe H. Antimicrob. Agents Chemother. 2001; 45: 956
- 12a Jajere SM. Vet. World 2019; 12: 504
- 12b Eng S.-K, Pusparajah P, Ab Mutalib N.-S, Ser H.-L, Chan K.-G, Lee L.-H. Front. Life Sci. 2015; 8: 284
- 13a Fair RJ, Tor Y. Perspect. Med. Chem. 2014; 6: 25
- 13b Appelbaum PC. J. Antimicrob. Chemother. 2012; 67: 2062
- 13c Sipahi OR. Expert Rev. Anti-Infect. Ther. 2008; 6: 523
- 14a Moxon ER, Kroll JS. Curr. Top. Microbiol. Immunol. 1990; 150: 65
- 14b Taylor CM, Roberts IS. Contrib. Microbiol. 2005; 12: 55
- 15 Liu B, Perepelov AV, Svensson MV, Shevelev SD, Guo D, Senchenkova SN, Shashkov AS, Weintraub A, Feng L, Widmalm G, Knirel YA, Wang L. Glycobiology 2010; 20: 679
- 16 Gilchrist SA. N, Nanni A, Levine O. Am. J. Public Health 2012; 102: 596
- 17a Thindwa D, Quesada MG, Liu Y, Bennett J, Cohen C, Knoll MD, von Gottberg A, Hayford K, Flasche S. Vaccine 2020; 38: 5398
- 17b Nichol KL. Vaccine 1999; 17: S91
- 18a Pace D, Pollard AJ. Arch. Dis. Child. 2007; 92: 909
- 18b Poland GA. Clin. Infect. Dis. 2010; 50: S45
- 19a Gucchait A, Shit P, Misra AK. Tetrahedron 2020; 76: 131412
- 19b Dhara D, Baliban SM, Huo CX, Rashidijahanabad Z, Sears KT, Nick ST, Misra AK, Tennant SM, Huang X. Chem. Eur. J. 2020; 26: 15953
- 19c Huo C.-X, Dhara D, Baliban SM, Nick ST, Tan Z, Simon S, Misra AK, Huang X. Chem. Commun. 2019; 55: 4519
- 19d Bhaumik I, Misra AK. ChemistrySelect 2017; 2: 3065
- 19e Bhaumik I, Misra AK. ChemistrySelect 2017; 2: 937
- 19f Dhara D, Misra AK. ChemistryOpen 2015; 4: 768
- 19g Dhara D, Mandal PK, Misra AK. Tetrahedron: Asymmetry 2014; 25: 263
- 19h Ghosh T, Santra A, Misra AK. Tetrahedron: Asymmetry 2013; 24: 606
- 19i Sau A, Panchadhayee R, Ghosh D, Misra AK. Carbohydr. Res. 2012; 352: 18
- 20 Nicolaou KC, Bockovich NJ, Carcanague DR, Hummel CW, Even LF. J. Am. Chem. Soc. 1992; 114: 8701
- 21 Kalikanda J, Li Z. J. Org. Chem. 2011; 76: 5207
- 22 Hsu Y, Lu X.-A, Zulueta ML, Tsai C.-M, Lin K.-I, Hung S.-C, Wong C.-H. J. Am. Chem. Soc. 2012; 134: 4549
- 23 Huang T.-Y, Zulueta MM. L, Hung S.-C. Org. Biomol. Chem. 2014; 12: 376
- 24a Mukherjee C, Misra AK. Synthesis 2007; 683
- 24b Manna T, Gucchait A, Misra AK. Beilstein J. Org. Chem. 2020; 16: 106
- 24c Shit P, Misra AK. Glycoconjugate J. 2020; 37: 647
- 24d Kundu M, Gucchait A, Misra AK. Tetrahedron 2020; 76: 130952
- 24e Manna T, Misra AK. Carbohydr. Res. 2021; 502: 108294
- 24f Kundu M, Misra AK. Carbohydr. Res. 2019; 486: 107830
- 24g Shit P, Gucchait A, Misra AK. Tetrahedron 2019; 75: 130697
- 25 Chakraborti AK, Gulhane R. Chem. Commun. 2003; 1896
- 26a Khatik GL, Sharma G, Kumar R, Chakraborti AK. Tetrahedron 2007; 63: 1200
- 26b Kumar D, Kommi DN, Chebolu R, Garg SK, Kumar R, Chakraborti AK. RSC Adv. 2013; 3: 91
- 26c Kumar D, Sonawane M, Pujala B, Jain VK, Bhagat S, Chakraborti AK. Green Chem. 2013; 15: 2872
- 26d Rudrawar S, Besra RC, Chakraborti AK. Synthesis 2006; 2767
- 26e Kumar R, Kumar D, Chakraborti AK. Synthesis 2007; 299
- 26f Chakraborti AK, Sunay V, Chankeshwara SV. Org. Biomol. Chem. 2006; 4: 2769
- 26g Agarwal A, Rani S, Vankar YD. J. Org. Chem. 2004; 69: 6137
- 26h Misra AK, Tiwari P, Madhusudan SK. Carbohydr. Res. 2005; 340: 325
- 26i Misra AK, Tiwari P, Agnihotri G. Synthesis 2005; 260
- 26j Khan AT, Choudhury LH, Ghosh S. J. Mol. Catal. A: Chem. 2006; 255: 230
- 26k Ansari MI, Hussain MK, Yadav N, Gupta PK, Hajela K. Tetrahedron Lett. 2012; 53: 2063
- 27a Das R, Mukhopadhyay B. ChemistryOpen 2016; 5: 401
- 27b Lian G, Zhang X, Yu B. Carbohydr. Res. 2015; 403: 13
- 27c Codée JD. C, Litjens RE. J. N, van den Bos LJ, Overkleeft HS, van der Marel GA. Chem. Soc. Rev. 2005; 34: 769
- 28 Adak A, Mukhopadhyay B. Carbohydr. Res. 2019; 476: 1
- 29 Kiyoi T, Nakai Y, Kondo H, Ishida H, Kiso M, Hasegawa A. Bioorg. Med. Chem. 1996; 4: 1167
- 30 Brimacombe JS. Methods Carbohydr. Chem. 1972; 6: 376
- 31 Wuts PG. M. In Handbook of Reagents for Organic Synthesis: Reagents for Glycoside, Nucleotide, and Peptide Synthesis. Crich D. Wiley; Chichester: 2005: 425
- 32 Dong H, Rahm M, Thota N, Deng L, Brinck T, Ramström O. Org. Biomol. Chem. 2013; 11: 648
- 33 Augé C, David S, Veyrières A. J. Chem. Soc., Chem. Commun. 1976; 375
- 34 Dhakal B, Bohé L, Crich D. J. Org. Chem. 2017; 82: 9263
- 35 Lloyd D, Bylsma M, Bright DK, Chen X, Bennett CS. J. Org. Chem. 2017; 82: 3926
- 36 Lee H.-H, Schwartz DA, Harris JF, Carver JP, Krepinsky JJ. Can. J. Chem. 1986; 64: 1912
- 37 Shangguan N, Katukojvala S, Greenberg R, Williams LJ. J. Am. Chem. Soc. 2003; 125: 7754
- 38 Pearlman WM. Tetrahedron Lett. 1967; 8: 1663