Carbohydrate-based synthetic vaccines: Does the synthesis of longer chains of carbohydrates make this a step ever closer?

Future Medicinal Chemistry

Volumn 4, Issue 14, 2012, Pages 1767-1770

  Chu, Kuo Ching ^a   Wu, Chung Yi ^a  

^a GENOMICS RESEARCH CENTER   (Taiwan)

Author keywords

chemical synthesis; conjugate vaccine; oligosaccharide; polysaccharide vaccine; synthetic vaccine

Indexed keywords

BACTERIAL VACCINE; CANCER VACCINE; CARBOHYDRATE; OLIGOSACCHARIDE; POLYSACCHARIDE;

CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; DRUG SYNTHESIS; GLYCOSYLATION; IMMUNE RESPONSE; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; PRIORITY JOURNAL; REVIEW; STRUCTURE ACTIVITY RELATION; SYNTHETIC BIOLOGY; X RAY;

BACTERIA; BACTERIAL INFECTIONS; BACTERIAL VACCINES; CARBOHYDRATES; CHEMISTRY TECHNIQUES, SYNTHETIC; HUMANS; VACCINES, SYNTHETIC;

EID: 84867363591     PISSN: 17568919     EISSN: 17568927     Source Type: Journal    
DOI: 10.4155/fmc.12.102     Document Type: Review

References (22)

1. Astronomo RD, Burton DR. Carbohydrate vaccines. Developing sweet solutions to sticky situations? Nat. Rev. Drug Discov. 9(4), 308-324 (2010).
2. Hevey R, Ling CC. Recent advances in developing synthetic carbohydrate-based vaccines for cancer immunotherapies. Future Med. Chem. 4(4), 545-584 (2012).
3. Ling CC, Bundle DR. Eliciting carbohydrate-specific immune response against sialosides. Success and challenges. Future Med. Chem. 3(5), 519-534 (2011).
4. Brubaker JO, Li Q, Tzianabos AO, Kasper DL, Finberg RW. Mitogenic activity of purified capsular polysaccharide A from Bacteroides fragilis. Differential stimulatory effect on mouse and rat lymphocytes in vitro. J. Immunol. 162(4), 2235-2242 (1999). (Pubitemid 29288846)
5. Bundle DR. New Frontiers in the Chemistry of Glycoconjugate Vaccines. Caister Academic Press, Norfolk, UK 69-107 (2011).
6. Bardotti A, Averani G, Berti F et al. Physicochemical characterisation of glycoconjugate vaccines for prevention of meningococcal diseases. Vaccine 26(18), 2284-2296 (2008).
7. Michon F, Uitz C, Sarkar A et al. Group B streptococcal type II and III conjugate vaccines. Physicochemical properties that influence immunogenicity. Clin. Vaccine Immunol. 13(8), 936-943 (2006). (Pubitemid 44409634)
8. Benaissa-Trouw B, Lefeber DJ, Kamerling JP, Vliegenthart JFG, Kraaijeveld K, Snippe H. Synthetic polysaccharide type 3-related di-, tri-, and tetrasaccharide-CRM197 conjugates induce protection against Streptococcus pneumoniae type 3 in mice. Infect. Immun. 69(7), 4698-4701 (2001). (Pubitemid 32574477)
9. Verez-Bencomo V, Fernandez-Santana V, Hardy E et al. A synthetic conjugate polysaccharide vaccine against Haemophilus influenzae type b. Science 305, 522-525 (2004). (Pubitemid 38971343)
10. Wang CC, Lee JC, Luo SY et al. Regioselective one-pot protection of carbohydrates. Nature 446(7138), 896-899 (2007).
11. Zhang ZY, Ollmann IR, Ye XS, Wischnat R, Baasov T, Wong CH. Programmable one-pot oligosaccharide synthesis. J. Am. Chem. Soc. 121(4), 734-753 (1999).
12. Nicolaou KC, Watanabe N, Li J, Pastor J, Winssinger N. Solid-phase synthesis of oligosaccharides. Construction of a dodecasaccharide. Angew. Chem. Int. Ed. 37(11), 1559-1561 (1998). (Pubitemid 28309836)
13. Plante OJ, Palmacci ER, Seeberger PH. Automated solid-phase synthesis of oligosaccharides. Science 291(5508), 1523-1527 (2001). (Pubitemid 32179214)
14. Jaipuri FA, Pohl NL. Toward solution-phase automated iterative synthesis. fluorous-tag assisted solution-phase synthesis of linear and branched mannose oligomers. Org. Biomol. Chem. 6(15), 2686-2691 (2008). (Pubitemid 352027698)
15. Lin CC, Adak AK, Horng JC. Phosphite-based sialic acid donors in the synthesis of alpha(2-> 9) oligosialic acids. Tetrahedron 65(24), 4714-4725 (2009).
16. Tanaka H, Nishiura Y, Takahashi T. Stereoselective synthesis of alpha(2,9) Di-to tetrasialic acids, using a 5,4-N,O-carbonyl protected thiosialoside. J. Org. Chem. 74(11), 4383-4386 (2009).
17. Lin CC, Huang KT. N-trifluoroacetyl sialyl phosphite donors for the synthesis of alpha(2-> 9) oligosialic acids. Org. Lett. 7(19), 4169-4172 (2005).
18. Mulard LA, Guerreiro C. Total synthesis of a tetra-and two pentasaccharide fragments of the O-specific polysaccharide of Shigella flexneri serotype 2a. Tetrahedron 60(11), 2475-2488 (2004). (Pubitemid 38249563)
19. Chu KC, Ren CT, Lu CP et al. Efficient and stereoselective synthesis of alpha(2-> 9) oligosialic acids. From monomers to dodecamers. Angew. Chem. Int. Ed. 50(40), 9391-9395 (2011).
20. Hsu CH, Hung SC, Wu CY, Wong CH. Toward automated oligosaccharide synthesis. Angew. Chem. Int. Ed. 50(50), 11872-11923 (2011).
21. Schmaltz RM, Hanson SR, Wong CH. Enzymes in the synthesis of glycoconjugates. Chem. Rev. 111(7), 4259-4307 (2011).
22. Levengood MR, Splain RA, Kiessling LL. Monitoring processivity and length control of a carbohydrate polymerase. J. Am. Chem. Soc. 133(32), 12758-12766 (2011).