A chemically contiguous hapten approach for a heroin–fentanyl vaccine

• Yoshihiro Natori,
• Candy S. Hwang,
• Lucy Lin,
• Lauren C. Smith,
• Bin Zhou and
• Kim D. Janda

Beilstein J. Org. Chem. 2019, 15, 1020–1031, doi:10.3762/bjoc.15.100

• respiratory depression. Indeed, anti-drug vaccines for individual conjugate vaccines of fentanyl and heroin have already exhibited protection in several animal models [3][4][5][6][7][8]. Antidrug vaccines targeting multiple, structurally distinct species are not common and have utilized two tactics: 1) mixing

• individual heroin and fentanyl conjugate vaccines against challenges of 10–20% fentanyl in heroin [13][14]. Gratifyingly, we found these admixture vaccines were able to produce antibodies with excellent affinity toward both drugs, as well as six other analogues of fentanyl. Moreover, the heroin–fentanyl

• the synthesis of nine unique chemically contiguous heroin–fentanyl haptens and their evaluation as conjugate vaccines to induce a polyclonal antibody response, as measured by ELISA, surface plasmon resonance (SPR), and in a behavioral assay (Figure 1). Results As a starting point for our exploration

Total synthesis of a Streptococcus pneumoniae serotype 12F CPS repeating unit hexasaccharide

• Peter H. Seeberger,
• Claney L. Pereira and
• Subramanian Govindan

Beilstein J. Org. Chem. 2017, 13, 164–173, doi:10.3762/bjoc.13.19

• polysaccharides (CPS) that surround them, are responsible for about 90% of infections worldwide [7]. The licensed polysaccharide vaccine Pneumovax 23 contains serotype 12F but is not efficacious in young children or elderly people, those at highest risk. The carbohydrate conjugate vaccines Prevanar13™ and

Automated glycan assembly of a S. pneumoniae serotype 3 CPS antigen

• Markus W. Weishaupt,
• Stefan Matthies,
• Mattan Hurevich,
• Claney L. Pereira,
• Heung Sik Hahm and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2016, 12, 1440–1446, doi:10.3762/bjoc.12.139

• conclusion, we have developed an efficient method for the synthesis of S. pneumoniae serotype 3 CPS structures. The products of these syntheses are currently used in the development of synthetic carbohydrate conjugate vaccines. Disaccharide repeating unit of the S. pneumoniae serotype 3 CPS. Building blocks

Synthesis and biological evaluation of a novel MUC1 glycopeptide conjugate vaccine candidate comprising a 4’-deoxy-4’-fluoro-Thomsen–Friedenreich epitope

• Manuel Johannes,
• Maximilian Reindl,
• Bastian Gerlitzki,
• Edgar Schmitt and
• Anja Hoffmann-Röder

Beilstein J. Org. Chem. 2015, 11, 155–161, doi:10.3762/bjoc.11.15

• to rapid in vivo degradation. To overcome these drawbacks, novel fluorinated MUC1 glycopeptide-BSA/TTox conjugate vaccines have been prepared. Immunization of mice with the 4’F-TF-MUC1-TTox conjugate resulted in strong immune responses overriding the natural tolerance against MUC1 and producing

• , which becomes accessible to the immune system and can be used as an additional immunogenic determinant for carbohydrate-based cancer vaccines [13]. Despite encouraging results with two- and three-component MUC1 conjugate vaccines in mice models [14][15][16][17][18][19][20][21][22][23][24][25], immune

Synthetic glycopeptides and glycoproteins with applications in biological research

• Ulrika Westerlind

Beilstein J. Org. Chem. 2012, 8, 804–818, doi:10.3762/bjoc.8.90

• furthermore been evaluated [31][32][33]. Synthetic MUC1-tetanus toxoid conjugate vaccines have proven to be particularly interesting. Tetanus toxoid vaccines conjugated to other antigens have been administered to humans. During immunization in mice, highly specific and strong immune responses were induced in

• containing a Toll-like receptor-2 (TLR2) ligand have, moreover, been synthesized and evaluated [35][36][37][38]. These self-adjuvanting vaccines avoid invoking an immune response to the immune carrier, a problem commonly seen upon employing protein conjugate vaccines. The synthesis of two-component vaccines

• offer multivalent presentation and fine-tuning in studies of specific protein-binding events. Tumor-associated glycosylation on MUC1 tandem repeat peptides. Di- and trivalent glycopeptide dendrimers evaluated for FimH inhibition. Synthesis of MUC1 tetanus toxoid protein conjugate vaccines. TN, T and

Synthesis of 6-PEtN-α-D-GalpNAc-(1–>6)-β-D-Galp-(1–>4)-β-D-GlcpNAc-(1–>3)-β-D-Galp-(1–>4)-β-D-Glcp, a Haemophilus influenzae lipopolysacharide structure, and biotin and protein conjugates thereof

• Andreas Sundgren,
• Martina Lahmann and
• Stefan Oscarson

Beilstein J. Org. Chem. 2010, 6, 704–708, doi:10.3762/bjoc.6.80

• the title compound have been constructed to allow further use in biological experiments. Keywords: conjugate vaccines; glycoconjugates; Haemophilus influenzae; lacto-N-neotetraose; oligosaccharide synthesis; thioglycosides; Introduction Haemophilus influenzae are Gram-negative bacteria divided into