Chemical Processes Involving 18‐Crown‐6‐Ether in Activated Noncovalent Complexes with Protonated Peptides

Abdelmouleh, Marwa; Lalande, Mathieu; Nicol, Édith; Frison, Gilles; Rest, Guillaume van der; Poully, Jean‐Christophe

doi:10.1002/cphc.202100075

Cited by 1 publication

(2 citation statements)

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“…It is known that non-covalent complex reactions between 18C6 and peptide facilitated peptide sequencing after complex activation by collisions in argon or electron capture/ transfer. [29] Since covalently bound 4fb18C6 should produce the same effect after collisions with argon, our first goal was to select a group of peptides to test this hypothesis. A total of 23 peptides from six proteins with different amino acid compositions were selected according to their length and polarity.…”

Section: Resultsmentioning

confidence: 99%

“…Furthermore, these studies have shown that CEs are able to change their binding site after electron transfer. [29] Based on these results, we performed a series of CID-MS experiments in positive ion mode with intact and derivatized peptides using ESI to investigate the effects of labelling the N-terminus of peptides with 4fb18C6 as a potential reagent for de novo sequencing. The derivatization reaction takes place between the formyl group of 4fb18C6 and the amino group of the peptide under slightly acidic conditions (pH 6).…”

Section: Introductionmentioning

confidence: 99%

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N-Terminal Derivatization of Peptides with 4'-Formylbenzo-18-crown-6-ether for Protein and Species Identification

Ozdanovac,

Biba,

Erk

et al. 2024

Croat. Chem. Acta

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Our research objective was to investigate the use of 4 '-formylbenzo-18-crown-6-ether (4fb18C6) for the covalent labelling of peptides for unambiguous peptide identification. Specifically, 23 peptides were analysed using a coupled system of liquid chromatography and tandem mass spectrometry with electrospray ionization to test de novo sequencing of derivatized and intact peptides. The reaction was optimized for reductive amination to be performed in an aqueous medium at pH 6 using the microwave radiation. After matching the tandem mass spectra of derivatized and intact peptides in the range of ±0.005 Da, the chemical noise was reduced by up to 90 % and six proteins from 17 different species were identified using the BLASTp algorithm (NCBInr and UniProtKB/Swiss-Prot databases). Species identification enabled further accelerated database search using the classical method of mass spectra database matching. The presented method enables reliable de novo sequencing of peptides and represents a new tool for species identification.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

N-Terminal Derivatization of Peptides with 4'-Formylbenzo-18-crown-6-ether for Protein and Species Identification

Ozdanovac,

Biba,

Erk

et al. 2024

Croat. Chem. Acta

View full text Add to dashboard Cite

show abstract

Chemical Processes Involving 18‐Crown‐6‐Ether in Activated Noncovalent Complexes with Protonated Peptides

Abstract: Supporting information for this article is given via a link at the end of the document.

Cited by 1 publication

References 40 publications

N-Terminal Derivatization of Peptides with 4'-Formylbenzo-18-crown-6-ether for Protein and Species Identification

N-Terminal Derivatization of Peptides with 4'-Formylbenzo-18-crown-6-ether for Protein and Species Identification

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