Synthetic strategies of phosphonodepsipeptides

• Jiaxi Xu

Beilstein J. Org. Chem. 2021, 17, 461–484, doi:10.3762/bjoc.17.41

• and phosphonate-linked analogues of naturally occurring peptides. They are more stable than phosphonopeptides and have been widely applied as enzyme inhibitors, haptens for the production of antibodies, biological agents, and prodrugs. The synthetic strategies towards phosphonodepsipeptides are

• than the corresponding phosphonopeptides because the phosphonate bond is more inert than a phopshonamidate bond. Phosphonodepsipeptides are widely used as enzyme inhibitors [6][7][8][9][10], haptens for inducing catalytic antibodies [11][12], and produgs [8][9][13]. They have potential applications as

• , haptens for the production of antibodies, biological agents, and prodrugs. Various synthetic methods of phosphonodepsipeptides have been developed, including the phosphonylation of hydroxy esters with phosphonochloridates or with phosphonic monoesters in the presence of coupling reagents, the alkylation

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

• . The current study examines an approach for combatting the dangers of fentanyl-laced heroin, by using a hapten with one epitope that has domains for both fentanyl and heroin. Results: We evaluated a series of nine vaccines developed from chemically contiguous haptens composed of both heroin- and

• competent antibody–drug response and memory generation. To test this notion, we envisioned two drug haptens chemically joined to produce a colocalized epitope by chemical design. While success of such an approach would have undeniable challenges, all data gathered would at the very least provide insight

• 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

Synthesis and immunological evaluation of protein conjugates of Neisseria meningitidis X capsular polysaccharide fragments

• Laura Morelli,
• Damiano Cancogni,
• Marta Tontini,
• Alberto Nilo,
• Sara Filippini,
• Paolo Costantino,
• Maria Rosaria Romano,
• Francesco Berti,
• Roberto Adamo and
• Luigi Lay

Beilstein J. Org. Chem. 2014, 10, 2367–2376, doi:10.3762/bjoc.10.247

• fragments, based on the synthetic improvements and also the benefits of the continuous-flow microreactor technology herein described, is currently ongoing in our laboratory and it will be reported in due course. Besides the length of the carbohydrate haptens, the saccharide loading onto the protein is

Convergent synthesis of the tetrasaccharide repeating unit of the cell wall lipopolysaccharide of Escherichia coli O40

• Abhijit Sau and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2012, 8, 2053–2059, doi:10.3762/bjoc.8.230

• therapeutics against this organism. Since, bacterial cell-wall lipopolysaccharides play important roles in the pathogenicity of the virulent strains, it would be pertinent to develop glycoconjugate therapeutics based on the cell-wall oligosaccharide haptens to reduce the number of infections [9][10][11][12

Synthesis of glycoconjugate fragments of mycobacterial phosphatidylinositol mannosides and lipomannan

• Benjamin Cao,
• Jonathan M. White and
• Spencer J. Williams

Beilstein J. Org. Chem. 2011, 7, 369–377, doi:10.3762/bjoc.7.47

• elaboration to fluorescently-labelled glycoconjugates and haptens for the preparation of antigens. A readily prepared and crystalline 1,2-O-benzylidene acetal 18 has been used as a central precursor for the preparation of 2-O-acetyl mannosyl donors 16 and 17. The synthetic routes are compatible with the azido

An expedient synthesis of 5-n-alkylresorcinols and novel 5-n-alkylresorcinol haptens

• Kirsti Parikka and
• Kristiina Wähälä

Beilstein J. Org. Chem. 2009, 5, No. 22, doi:10.3762/bjoc.5.22

• analogues and haptens, which have not been previously prepared, were synthesised. Microwave-promoted reactions of a semi-stabilized ylid and alkanals in water gave good yields in both pressurized and open systems. An alternative microwave-promoted synthesis starting from non-stabilized

• way for the immunochemical detection techniques of alkylresorcinols. Keywords: 5-n-alkylresorcinols; haptens; microwave assisted synthesis; Wittig reaction; Introduction 5-Alk(en)ylresorcinols and related compounds are phenolic lipids present in several families of plants (e.g. Gramineae

• . We also report that the use of microwave (MW) irradiation brings major benefits as regards reaction times and yields in aqueous Wittig reactions. Both semi-stabilized and non-stabilized ylids provide an expedient entry to 5-(1-alkenyl)resorcinols, readily converted to AR and AR haptens. Results and