Scope and limitations of pseudoprolines as individual amino acids in peptide synthesis

Senko, Dmitry A.; Timofeev, Nikita D.; Kasheverov, Igor E.; Ivanov, Igor A.

doi:10.1007/s00726-021-02973-1

Cited by 10 publications

(19 citation statements)

References 15 publications

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“…For acylation with Fmoc-Arg(Pbf)-OH, a coupling without preactivation was also attempted to minimize the δ-lactam formation. 25 …”

Section: Resultsmentioning

confidence: 99%

“…Furthermore, acylation on tetrapeptide was studied with different Fmoc-AA-OH [(Gly, Phe, Ile, Thr( t Bu), and Arg(Pbf)] using DIC-OxymaPure (5 equiv each, single coupling for 2 h, with 2 min of preactivation) as the coupling method. For acylation with Fmoc-Arg(Pbf)-OH, a coupling without preactivation was also attempted to minimize the δ-lactam formation …”

Section: Resultsmentioning

confidence: 99%

“…Herein, we complemented the study of Senko et al 25 regarding the use of monomeric Fmoc-Ser(ψ Me,Me pro)-OH and applied it to the synthesis of a so far “inaccessible” peptide, according to the term used by Mutter and co-workers for difficult-to-synthesize peptides. 18…”

Section: Introductionmentioning

confidence: 99%

“…With the concourse of Fmoc-AA-Ser/Thr[ψ Me,Me pro]-OH being commercially available, a large number of difficult peptides have been synthesized in moderate to excellent yields. − In a practical manner, the use of this excellent synthetic tool was limited to the presence of Ser or Thr in the sequence and to the commercial availability of the required ψPro dipeptide. Recently, Senko et al have published the synthesis of the Fmoc monomers (Fmoc-Ser/Thr(ψ Me,Me pro)-OH) (Figure ) and the scope and limitations of their use in peptide elongation, allowing a much broader use of this technique.…”

Section: Introductionmentioning

confidence: 99%

“…21−24 In a practical manner, the use of this excellent synthetic tool was limited to the presence of Ser or Thr in the sequence and to the commercial availability of the required ψPro dipeptide. Recently, Senko et al 25 have published the synthesis of the Fmoc monomers (Fmoc-Ser/ Thr(ψ Me,Me pro)-OH) (Figure 1) and the scope and limitations of their use in peptide elongation, allowing a much broader use of this technique. Herein, we complemented the study of Senko et al 25 regarding the use of monomeric Fmoc-Ser(ψ Me,Me pro)-OH and applied it to the synthesis of a so far "inaccessible" peptide, according to the term used by Mutter and co-workers for difficult-to-synthesize peptides.…”

Section: ■ Introductionmentioning

confidence: 99%

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Solid-Phase Synthesis of an “Inaccessible” hGH-Derived Peptide Using a Pseudoproline Monomer and SIT-Protection for Cysteine

Manne

Chakraborty

Rustler³

et al. 2022

ACS Omega

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The solid-phase peptide synthesis (SPPS) of the C-terminal sequence of hGH with one extra Tyr attached to its N-terminus (total of 16 residues with a disulfide bridge) has been accomplished for the first time by optimizing several synthetic parameters. First of all, the two Ser residues (positions 9 and 13 of the molecule) have been introduced as a single amino acid, Fmoc-Ser(ψ Me,Me pro)-OH, demonstrating that the acylation of these hindered moieties is possible. This allows us to avoid the use of the corresponding dipeptides, Fmoc-AA-Ser(ψ Me,Me pro)-OH, which are very often not commercially available or very costly. The second part of the sequence has been elongated via a double coupling approach using two of the most effective coupling methods (DIC-OxymaPure and HATU-DIEA). Finally, the disulfide bridging has been carried out very smoothly by a chemoselective thiol-disulfide interchange reaction between a SIT ( sec -isoamyl mercaptan)-protected Cys residue and the free thiol of the second Cys. The synthesis of this short peptide has evidenced that SPPS is a multifactorial process which should be optimized in each case.

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“…For acylation with Fmoc-Arg(Pbf)-OH, a coupling without preactivation was also attempted to minimize the δ-lactam formation. 25 …”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%