Synthesis of 1,2,3-Triazole-Linked Glycoconjugates of N-(2-Aminoethyl)glycine: Building Blocks for the Construction of Combinatorial Glycopeptide Libraries

Abstract

Twenty-nine glycoconjugate building blocks based on the N-(2-aminoethyl)glycine (AEG) backbone and sugars linked to the backbone by a 1,2,3-triazole moiety were prepared via copper-catalyzed 1,3-dipolar cycloaddition of monosaccharides bearing an azide group and N-4-pentynoyl-AEG. The initial glycoconjugates were converted to the corresponding acids and pentafluorophenyl esters, respectively, which are useful building blocks for the construction of combinatorial glycopeptide libraries.

Key words

carbohydrates - glycopeptides - glycoconjugates - amino acids - azides

• References

• 1a Benett HS. Histochem. Cytochem. 1963; 11: 14
• 1b Lee YC, Lee RT. Acc. Chem. Res. 1995; 28: 321
• 1c Dwek RA. Chem. Rev. 1996; 96: 683
• 1d Solis D, Romero A, Menendez M, Jimenez-Barbero J In The Sugar Code . Gabius H.-J. Wiley-Blackwell; Weinheim: 2009
• 2a Bertozzi CR, Kiessling LL. Science 2001; 291: 2357
• 2b Audette GF, Delbaere LT. J, Xiang J. Curr. Protein Peptide Sci. 2003; 4: 11
• 2c Kiessling LL, Splain RA. Annu. Rev. Biochem. 2010; 79: 619
• 2d Kamiya Y, Yagi-Utsumi M, Yagi H, Kato K. Curr. Pharm. Design 2011; 17: 1672
• 3 Progress in the Synthesis of Complex Carbohydrate Chains of Plant and Microbial Polysaccharides. Nifantiev NE. Research Signpost; Trivandrum, India: 2009
• 4a Narla SN, Nie H, Li Y, Sun X.-L. J. Carbohydr. Chem. 2012; 31: 67
• 4b Sebestik J, Niederhafner JJ. Amino Acids 2011; 40: 301
• 4c Gamblin DP, Scanlan EM, Davis BG. Chem. Rev. 2009; 109: 131
• 4d Lundquist JJ, Toone EJ. Chem. Rev. 2002; 102: 555
• 5a Ziegler T, Röseling D, Subramanian LR. Tetrahedron: Asymmetry 2002; 13: 911
• 5b Schips C, Ziegler T. J. Carbohydr. Chem. 2005; 24: 773
• 5c Ziegler T, Schips C. Nat. Protoc. 2006; 1: 1987
• 5d Pietrzik N, Schips C, Ziegler T. Synthesis 2008; 519
• 5e Günther K, Schips C, Ziegler T. J. Carbohydr. Chem. 2008; 27: 446
• 5f Daiber R, Ziegler T. ARKIVOC 2013; (ii): 408
• 6a Beckmann HS. G, Niederwieser A, Wiessler M, Wittmann V. Chem. Eur. J. 2012; 18: 6548
• 6b Wittmann V, Pieters RJ. Chem. Soc. Rev. 2013; 42: 4492
• 6c Wehner JW, Hartmann M, Lindhorst TK. Carbohydr. Res. 2013; 371: 22
• 6d Sato K, Hada N, Takeda T. Tetrahedron Lett. 2003; 44: 9331
• 7a Nishida Y, Takamori Y, Matsuda K, Ohrui H, Yamada T, Kobayashi K. J. Carbohydr. Chem. 1999; 18: 985
• 7b Dohi H, Nishida Y, Mizuno M, Shinkai M, Kobayashi T, Takeda T, Uzawa H, Kobayashi K. Bioorg. Med. Chem. 1999; 7: 2035
• 7c Su L, Zhao Y, Chen G, Jiang M. Polymer Chem. 2012; 3: 1560
• 7d Grabosch C, Kolbe K, Lindhorst TK. ChemBiochem. 2012; 13: 1874
• 8 Nielsen PE, Egholm M, Berg RH, Buchardt O. Science 1991; 254: 1497
• 9a Tornoe CW, Christensen C, Meldal M. J. Org. Chem. 2002; 67: 3057
• 9b Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
• 9c Dedola S, Nepogodiev SA, Field RA. Org. Biomol. Chem. 2007; 5: 1006
• 9d Angell YL, Burgess K. Chem. Soc. Rev. 2007; 36: 1674
• 9e Moses JE, Moorhouse AD. Chem. Soc. Rev. 2007; 36: 1249
• 9f Singhamahapatra A, Sahoo L, Loganathan D. J. Org. Chem. 2013; 78: 10329
• 9g Woicik F, Lel S, O’Brien AG, Seeberger PH, Hartmann L. Beilstein J. Org. Chem. 2013; 9: 2395
• 9h Chang T.-C, Lai C.-H, Chien C.-W, Liang C.-F, Adak AK, Chuang Y.-J, Chen Y.-J, Lin C.-C. Bioconjugate Chem. 2013; 24: 1895
• 10 Cng H, Cao X, Xian M, Fang L, Cai TB, Ji JJ, Tunac JB, Sun D, Wang PG. J. Med. Chem. 2005; 48: 645
• 11 Nakabayashi A, Yamauchi H, Hasegawa A. Jpn. Kokai Tokkyo Koho JP05222085 A 19930831, 1993 ; Chem. Abstr. 1994, 66, 107634.
• 12 Mehta S, Meldal M, Ferro V, Duus JO, Bock K. J. Chem. Soc., Perkin Trans. 1 1997; 1365
• 13 Murphy PV, O’Brien JL, Gorey-Feret LJ, Smith AB. Tetrahedron 2003; 59: 2259
• 14 Dorner S, Westermann B. Chem. Commun. 2005; 2852
• 15 Maunier V, Boullanger P, Lafont D, Chevalier Y. Carbohydr. Res. 1997; 299: 49
• 16 Joseph R, Dyer FD, Garner P. Org. Lett. 2013; 15: 732
• 17 Joosten JA. F, Evers B, van Kamerling JP, Vliegenthart JF. G. Eur. J. Org. Chem. 2003; 3569
• 18 Ikeda K, Kimura F, Sano K, Suzuki Y, Achiwa K. Carbohydr. Res. 1998; 312: 183
• 19 Driowya M, Bougrin K, Banhida R. Synth. Commun. 2013; 43: 1808
• 20 Neumann J, Thiem J. Eur. J. Org. Chem. 2010; 900
• 21 Orth R, Pitscheider M, Sieber SA. Synthesis 2010; 2201
• 22 Lee DJ, Mandal K, Harris PW. R, Brimble MA, Kent SB. H. Org. Lett. 2009; 11: 5270
• 23 Goddard-Borger ED, Stick RV. Org. Lett. 2007; 9: 3797
• 24a Lemieux RU, Ratcliffe RM. Can. J. Chem. 1979; 57: 1244
• 24b Lemieux RU, Huber G. Ger. Offen DE 2816340 A1 19781019, 1978 ; Chem. Abstr. 1979, 51, 87846.
• 25 Hainrichson M, Pokrovskaya V, Shallom-Shezifi D, Fridman M, Belakhov V, Shachar D, Yaron S, Baasov T. Bioorg. Med. Chem. 2005; 13: 5797
• 26 Todd LL, Hindsgaul O. Carbohydr. Res. 1994; 251: 33
• 27 Elchert B, Li J, Wang J, Hui Y, Rai R, Ptak R, Ward P, Takemoto JY, Bensaci M, Chang C.-WT. J. Org. Chem. 2004; 69: 1513
• 28 Lemieux RU, Huber G. Can. J. Chem. 1953; 31: 1040
• 29 Chittenden GJ. F. Carbohydr. Res. 1988; 183: 140
• 30 Hollfelder F, Golicnik M, Olguin LF, Feng GQ, Baxter NJ, Waltho JP, Williams NH. J. Am. Chem. Soc. 2009; 131: 1575
• 31 Danac R, Ball L, Gurr SJ, Fairbanks AJ. Carbohydr. Res. 2008; 343: 1012
• 32 Batey JF, Bullock C, O’Brien E, Williams JM. Carbohydr. Res. 1975; 43: 43
• 33 Griffith BR, Krepel C, Fu X, Blanchard SA, Edmiston CE, Thorson JS. J. Am. Chem. Soc. 2007; 129: 8150
• 34 Vourloumis D, Winters GC, Simonsen KB, Takahashi M, Ayida BK, Shandrick S, Zhao Q, Han Q, Hermann T. ChemBioChem 2005; 6: 58
• 35 Carboni B, Vaultier M, Carrié R. Tetrahedron 1987; 43: 1799
• 36 Gasser G, Hüsken N, Köster SD, Metzler-Nolte N. Chem. Commun. 2008; 3675
• 37a Chen S.-M, Mohan V, Kieley JS, Griffith MC, Griffey RH. Tetrahedron Lett. 1994; 35: 5105
• 37b Oleszczuck M, Rodziewicz-Motowidlo S, Falkiewicz B. Nucleosides Nucleotides 2001; 20: 1399