The application of anisole in greener solid-phase peptide synthesis protocols – Compatibility with green bases in Fmoc removal and new green binary mixture for coupling

Přibylka, Adam; Pastorek, Milan; Grepl, Martin; Schütznerová, Eva

doi:10.1016/j.tet.2021.132452

Cited by 22 publications

(15 citation statements)

References 71 publications

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“…Next, using the CTC resin and Trt as the protecting group for Cys and the peptide Boc-Leu-Ala-Cys(Trt)-O-CT-resin as a model, several secondary cyclic amines, namely, piperidine (PP), 4-methylpiperidine (4 MP), , piperazine (PZ), pyrrolidine (PY), and morpholine (MOP), , were studied (Figure ). Furthermore, in some cases, an acid rectifier, OxymaPure, was added to achieve a buffer impact, which has been demonstrated to reduce the formation of other side products such as aspartimides and δ-lactams. − …”

Section: Resultsmentioning

confidence: 99%

Solid-Phase Synthesis of C-Terminus Cysteine Peptide Acids

Mthembu

Chakraborty

Schönleber

et al. 2022

Org. Process Res. Dev.

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Cysteine (Cys) is a key amino acid in many therapeutic peptides. For research and industrial purposes, solid-phase peptide synthesis is the method of choice for the preparation of most peptides. The solid-phase synthesis of C-terminal Cys peptide acids is problematic because it is accompanied by a side reaction, namely, the abstraction of α-H from the Cys residue, which leads to the formation of three side products: the epimer and two N-piperidinyl-Ala epimer peptides. Here, we used a chlorotrityl chloride resin to conduct a rational and in-depth study of this side reaction. The following variables were examined: removal of the fluorenylmethoxycarbonyl (Fmoc) group by different bases, the presence or absence of an acid rectifier for buffering the base, and thiol side-chain protection. In conclusion, the use of Fmoc-Cys protected with tetrahydropyran (Thp) and 4-methoxytrityl (Mmt) along with 30% 4-methylpiperidine in 0.5 M OxymaPure-DMF for Fmoc removal assures minimization of the side reaction, as demonstrated in a model peptide and confirmed for the elongation of somatostatin.

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Section: Resultsmentioning

confidence: 99%

Solid-Phase Synthesis of C-Terminus Cysteine Peptide Acids

Mthembu

Chakraborty

Schönleber

et al. 2022

Org. Process Res. Dev.

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“…Thus, a high concentration of anisole was produced from benzene (Figure 6.a). This substance is used as a precursor for perfumes and in the pharmaceutical and chemical industries and it is also considered as one of the greenest solvents [51,52] and can replace some hazardous ones, such as piperidine [53,54]. From toluene solutions, 2-methylanisole and 4-methylanisole are generated and, as can be seen both in the Figure 6.b.…”

Section: Changing the View: From Destruction To Conversionmentioning

confidence: 97%

Production of value-added substances from the electrochemical oxidation of volatile organic compounds in methanol medium

Mello

Arias

Motheo

et al. 2022

Chemical Engineering Journal

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“…In fact, due to the necessity to replace piperidine with bases displaying a better environmental, health and safety (EHS) profile, other bases are usually combined with green solvents and applied in some cases at lower concentrations to ensure efficient deprotections. In particular, 10% piperazine in DMF/EtOH, 49 50% morpholine in 2-MeTHF 47 or An, 43 Please do not adjust margins Please do not adjust margins…”

Section: Main Deprotectionmentioning

confidence: 99%