Abstract
Of the three classes of biopolymers—nucleic acids, proteins and glycoconjugates, nucleic acids and proteins have seen the most breakthroughs in understanding their biological role, in part due to their ready availability. The automation of oligonucleotide and peptide synthesis has been fruitful in providing biologists and biochemists with pure, well-defined structures. This work reviews the recent developments in the automated synthesis of oligosaccharides, the third class of biopolymers. Both glycosyl phosphates and glycosyl trichloroacetimidates have been used successfully in the automated assembly of oligosaccharides employing an octenediol-functionalized polystyrene resin. The product was cleaved either by methanolysis of an ester bond or by olefin cross metathesis. Several biologically important carbohydrates have been synthesized by automation, in a fraction of the time needed to synthesize them by traditional methods. For example, the tumor associated antigens Lewis Y, Ley-Lex, were synthesized by automation. A Leishmania cap tetrasaccharide and a malaria toxin vaccine candidate were also assembled.
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Varki A, Cummins R, Esko J, Freeze H, Hart G, Marth J (1999) Essentials of Glycobiology. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY
Rudd PM, Guile GR, Küster B, Harvey DG, Oppendaker G, Dwek RA (1997) Nature 388:205
Caruthers MH (1985) Science 230:281
Merrifield RB (1985) Angew Chem Int Ed Engl 24:799
Khan SH, O'Neill RA (1996) Modern Methods in Carbohydrate Synthesis. Harwood Academic, Amsterdam
Tanaka H, Matoba N, Tsukamoto H, Takimoto H, Yamada H, Takahashi T (2005) Synlett 2005:824
Zhang Z, Ollmann IR, Ye XS, Wischnat R, Baasov T, Wong CH (1999) J Am Chem Soc 121:734
Sears P, Wong CH (2001) Science 291:2344
Miura T, Goto K, Hosaka D, Inazu T (2003) Angew Chem Int Ed 42:2047
Ko KS, Jaipuri FA, Pohl NL (2005) J Am Chem Soc 127:13162
Mazoni L, Castelli R (2004) Org Lett 6:4195
Fumoto M, Hinou H, Ohta T, Ito T, Yamada K, Takimoto A, Kondo H, Shimizu H, Inazu T, Nakahara Y, Nishimura SI (2005) J Am Chem Soc 127:11804
Seeberger PH, Haase WC (2000) Chem Rev 100:4349
Fréchet JMJ, Schuerch C (1971) J Am Chem Soc 93:492
Plante OJ, Palmacci ER, Seeberger PH (2001) Science 291:1523
Bayer E (1991) Angew Chem, Int Ed Engl 30:113
Seneci P (2002) Solid-Phase Synthesis and Combinatorial Technologies. Wiley, New York
Andrade RB, Plante OJ, Melean LG, Seeberger PH (1999) Org Lett 1:1811
Love KR, Seeberger PH (2004) Angew Chem Int Ed 43:602
Fraser-Reid B, Udodong UE, Wu Z, Ottosson H, Merritt JR, Rao CS, Roberts C, Madsen R (1992) Synlett 1992:927
Buskas T, Soderberg E, Konradsson P, Fraser-Reid B (2000) J Org Chem 65:958
Pon RT (1993) Preparation od Solid Phase Supports. In: Agrawal S (ed) Methods in Molecular Biology 20: Protocols for Oligonucleotides and Analogues. Humana Press, Totowa, p 467
Werz DB, Castagner B, Seeberger PH (2007) J Am Chem Soc 129:2770–2771
Nicolaou KC, Pastor J, Winssinger N, Murphy F (1998) J Am Chem Soc 120:5132
Lütteke T, Bohne-Lang A, Loss A, Goetz T, Frank M, von der Lieth CW (2006) Glycobiol 16:71R
Hashimoto S, Honda T, Ikegami S (1989) J Chem Soc Chem Comm 685
Boger DL, Honda T (1994) J Am Chem Soc 116:5647
Duynstee HI, Wijsam ER, van deer Marel GA, van Boom JH (1996) Synlett 1996:313
Bohm G, Waldmann H (1996) Liebigs Ann Chem 1996:613
Plante OJ, Andrade RB, Seeberger PH (1999) Org Lett 1:211
Plante OJ, Palmacci ER, Andrade RB, Seeberger PH (1999) J Am Chem Soc 123:9545
Melean LG, Love KR, Seeberger PH (2002) Carbohydr Res 337:1893
Halcomb RL, Danishefsky SJ (1989) J Am Chem Soc 111:6661
Ravidà A, Liu X, Kovacs L, Seeberger PH (2006) Org Lett 8:1815
Schmidt RR, Michel J (1980) Angew Chem Int Ed Eng 19:731
Yu B, Tao H (2001) Tet Lett 42:2405
Yu B, Tao H (2002) J Org Chem 67:9099
Hewitt MC, Seeberger PH (2001) Org Lett 3:3699
McKenney D, Pouliot KL, Wang Y, Murthy V, Ulrich M, Döring G, Lee JC, Goldmann DA, Pier GB (1999) Science 284:1523
McKenney D, Pouliot KL, Wang Y, Murthy V, Ulrich M, Döring G, Lee JC, Goldmann DA, Pier GB (2000) J Biotechnol 83:37
Schofield L, Hewitt MC, Evans K, Siomos MA, Seeberger PH (2002) Nature 418:785
Hewitt MC, Snyder DA, Seeberger PH (2002) J Am Chem Soc 124:13434
Feizi T (2000) Glycobiology of AIDS. In: Ernst B, Hart GW, Sinaÿ P (ed) Carbohydrates in Chemistry and Biology, chap 52. Wiley-VCH, New York, pp 851–863
Lin G, Simmons G, Pohlmann S, Baribaud F, Ni HP, Leslie GJ, Haggarty B, Bates P, Weissman D, Hoxie JA, Doms RW (2003) J Virol 77:1337
Delmas B, Laude H (1991) Virus Res 20:107
Wu X, Grathwohl M, Schmidt RR (2002) Angew Chem Int Ed 41:4489
Jonke S, Liu KG, Schmidt RR (2006) Chem Eur J 12:1274
Ratner DM, Swanson ER, Seeberger PH (2003) Org Lett 5:4717
Ragupathi G, Deshpande PP, Coltart DM, Kim HM, Williams LJ, Danishefsky SJ, Livingston PO (2002) Int J Cancer 99:207
Zheng CS, Seeberger PH, Danishefsky SJ (1998) Angew Chem Int Ed Engl 37:786
Zhu T, Boons GJ (2001) Chem Eur J 7:2382
Love KR, Seeberger PH (2005) J Org Chem 70:3168
Carpino LA, Han GY (1972) J Org Chem 37:3404
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Castagner, B., Seeberger, P.H. (2007). Automated Solid Phase Oligosaccharide Synthesis. In: Bräse, S. (eds) Combinatorial Chemistry on Solid Supports. Topics in Current Chemistry, vol 278. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2007_124
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DOI: https://doi.org/10.1007/128_2007_124
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