Synthesis of medium and large phostams, phostones, and phostines

• Jiaxi Xu

Beilstein J. Org. Chem. 2023, 19, 687–699, doi:10.3762/bjoc.19.50

• phostine derivatives, less attention has been paid to the synthesis of medium and large phostam, phostone, and phostine derivatives. They are also biologically active compounds, such as inhibitors of the human farnesyl pyrophosphate synthase [21][22], antitumor agents [23], and hapten for the production of

• (71b) and 2-ethoxy-3-methyl-5-methylene-5,6,7-trihydro-1,2-oxaphosphepine 2-oxide (72b) in 85:15 in a total yield of 64% (Scheme 15) [36][37]. To prepare a hapten for the production of the catalytic antibody for the catalytic formation of a 14-membered lactone, because it is very difficult for the

• chemical synthesis of macrocyclic lactones which are the key structural motifs in some biologically active compounds, 14-methyl-2-phenoxy-1-oxa-2-phosphacyclotetradecane 2-oxide (74) was synthesized as the hapten from phenyl hydrogen (12-hydroxytridecyl)phosphonate (73) via Mitsunobu reaction. The

Synthetic strategies of phosphonodepsipeptides

• Jiaxi Xu

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

• chlorination. After the treatment of compound 39 with piperidine, the N-terminal free dipeptide was obtained and acylated with hexanedioic anhydride to afford the designed hapten 40 (Scheme 7) [11]. Phosphonodepsioctapeptide 41 was prepared as a variation of the partial sequence of a gene product of erb B-2

• depsidipeptide ᴅ-Ala-ᴅ-Lac was a new antibiotic strategy. In this regard, the phosphonodepsipeptide hapten 127 was designed to induce the antibody. First, N-Boc-(S)-1-aminoethylphosphinic acid (122) was coupled with benzyl alcohol in the presence of DCC as the coupling reagent, affording the benzyl N-Boc-1

• the protected phosphonodepsidipeptide 126 (Scheme 21) [12], that was further converted to the designed hapten 127. The new muramyl dipeptide (MDP) phosphorus analogue 131 related to LK 423 as potential immunomodulator was prepared by the coupling of methyl 1-(N-benzyloxycarbonyl)aminoethylphosphonate

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

• report of such a strategy in the opioid–drug–vaccine field. Keywords: antinociception; fentanyl; hapten; heroin; vaccine; Introduction In 2016, the Centers for Disease Control (CDC) estimated that approximately 20.4% of the U.S. population (e.g., 50 million people) was suffering from chronic pain [1

• two individual vaccines together (admixture vaccine) [9][10]; or 2) successive conjugation steps of one hapten and then the second to a carrier protein [11][12]. To specifically address the escalating incidence of fentanyl-contamination in heroin, we investigated the efficacy of an admixture of

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

• tolerance to carbohydrate antigens remains a major obstacle in initiating an effective and long-lasting immune protection against malignancies. One strategy to enhance the immunogenicity of carbohydrate antigens relies upon modification of the glycan hapten [26][27], which renders it more foreign to the

Catalysis: transition-state molecular recognition?

• Ian H. Williams

Beilstein J. Org. Chem. 2010, 6, 1026–1034, doi:10.3762/bjoc.6.117

• decrease in the energy of activation” [4]. A corollary to this insight was provided by W. P. (Bill) Jencks, who noted that a catalyst might be synthesised by raising an antibody to a hapten resembling the TS of the reaction to be catalysed: “the combining sites of such antibodies should be complementary to

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

• alkyltriphenylphosphonium salts and 3,5-dimethoxybenzaldehyde worked as well. Aqueous media were suitable for the reactions even if the starting materials were not soluble in water. The 5-n-alkylresorcinols are potential biomarkers of whole grain intake, and the new hapten derivatives of 5-n-alkylresorcinols will open the

• ) and odd carbon chain ylids, but its use is limited because of the poor availability of odd carbon chain alkyl bromides [28]. The synthesis of hapten derivatives of alkylresorcinols 2, potential compounds in the development of immunochemical analysis techniques, has not been reported previously. Only

• describes the synthesis of two 1-phenylalkenes in 20–30% yield using benzaldehyde and a CH2Cl2/H2O solvent [31]. We report here a fast and efficient synthesis of the long chain 5-n-alkylresorcinols 1 and the new potential hapten derivatives of 5-n-alkylresorcinols 2, ready for the development of antibodies