Stability and Cleavage Conditions of (2-Furyl)-L-Alanine-Containing Peptides

Schulz, Axel; Busmann, Annette; Klüver, Enno; Schnebel, Matthias; Adermann, Knut

doi:10.2174/0929866043406238

Cited by 5 publications

(4 citation statements)

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“…Furylalanine ( 10) is commercially available and was incorporated under standard peptide synthesis conditions. Though oxidation and degradation of the furan moiety during peptide synthesis had been described before, 101 and was observed when using 9 or 10 at the N terminus of a peptide, 102 an internal modification protected by the surrounding peptide did in our hands not present any problems. Furylalanine (10) was incorporated at two different positions in the known DNA-binding peptide sequence (DPAAL À KRARNTEA À ARRSRARKLQGGC).…”

Section: Dna-protein Cross-linkingsupporting

confidence: 49%

Furan oxidation based cross-linking: a new approach for the study and targeting of nucleic acid and protein interactions

et al. 2016

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Furan mediated nucleic acid cross-linking, initially developed for DNA interstrand duplex cross-linking, has matured into a versatile tool for the study of protein and nucleic acid interactions, ready to face its applications. The methodology was initially developed for easy and clean chemical generation of DNA interstrand cross-linked duplexes, but has been further expanded for use with other probes, targets and triggers, now allowing mild biologically significant cross-linking with potential therapeutic benefit. It was shown that the methodology could be repurposed for RNA interstrand cross-linking, which is very relevant in today's antisense approaches or miRNA target identification endeavors. This further illustrates the furan oxidation method's generality and mildness, especially when using red light for oxidation. A complementary antigene approach has been explored through duplex targeting with furan modified triplex forming oligonucleotides (TFOs) and DNA binding proteins. Also targeting of peptides and proteins by furan-modified DNA and peptides has been explored. Thorough methodology examination exploring variable reaction conditions in combination with a series of different furan-modified building blocks and application of different activation signals resulted in a detailed understanding of the mechanisms involved and factors influencing the yield and selectivity of the reaction. In order to draw the bigger picture of the scope and limitations of furan-oxidation cross-linking, we here provide a unique side by side comparison and discussion of our published data, supplemented with unpublished results, providing a clear performance report of the currently established furan toolbox and its application potential in various biomacromolecular complexes.

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Section: Dna-protein Cross-linkingsupporting

confidence: 49%

Furan oxidation based cross-linking: a new approach for the study and targeting of nucleic acid and protein interactions

et al. 2016

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“…Furthermore LC-MS analysis showed that none of the mass signals could be correlated to the expected product. As in 2004 Schulz and coworkers already reported the partial degradation of furan as a consequence of using TFA and scavengers, 22 we figured that the main problems occurred during the acidolytic cleavage of the peptide. To analyse the problems in detail and possibly remediate, the simpler pentamer sequence 2, for which side products are more easily analysed by LC-MS, was prepared as a test peptide on Wang resin.…”

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confidence: 68%

Aromatic capping surprisingly stabilizes furan moieties in peptides against acidic degradation

2012

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We herein describe the synthesis of furan containing peptides for further post-synthetic derivatisation in solution through our recently developed furan-oxidation-labeling technology. Previously, it was reported by others that during acidic cleavage of furan-modified peptides, furan moieties can suffer from degradation. We demonstrate here that this degradation is position dependent and can be fully suppressed through introduction of proximate aromatic residues. Versatile introduction of 2-furylalanine at internal, C-terminal as well as the sensitive N-terminal positions has now been proven possible.

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“…Unfortunately, most of the furylalanine did not survive classical peptide hydrolysis procedures in the presence of HCl (6 n). [30] Instead, pronase from Streptomyces griseus was successfully used to cleave the peptide bond. [31,32] The resulting amino acid solution was then directly derivatized with ethyl chloroformate (ECF).…”

Section: Resultsmentioning

confidence: 99%

How to Spoil the Taste of Insect Prey? A Novel Feeding Deterrent against Ants Released by Larvae of the Alder Leaf Beetle, Agelastica alni

et al. 2010

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Chemical defense of leaf beetle larvae (Chrysomelidae) against enemies is provided by secretions containing a wide range of deterrent compounds or by unpalatable hemolymph constituents. Here we report a new, very strong feeding deterrent against ants released by larvae of the alder leaf beetle Agelastica alni when attacked. The larvae release a defensive fluid from openings of pairwise, dorsolaterally located tubercles on the first to the eighth abdominal segments. The fluid, consisting of hemolymph and probably a glandular cell secretion, has previously been shown to contain a very stable, non-volatile feeding deterrent. The major deterrent component was isolated by repeated HPLC separation and analyzed by NMR and MS. The compound proved to be gamma-L-glutamyl-L-2-furylalanine (1), a novel dipeptide containing the unusual amino acid L-2-furylalanine. This amino acid, although synthetically well known, has not previously been reported from natural sources. The absolute configuration of the natural compound was elucidated by enantioselective gas chromatography after derivatization. The structure of the dipeptide was verified by the synthesis of several isomeric dipeptides. In bioassays a concentration of 1 microg microL(-1) was sufficient to deter polyphagous Myrmica rubra ants from feeding.

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Stability and Cleavage Conditions of (2-Furyl)-L-Alanine-Containing Peptides

Cited by 5 publications

References 0 publications

Furan oxidation based cross-linking: a new approach for the study and targeting of nucleic acid and protein interactions

Furan oxidation based cross-linking: a new approach for the study and targeting of nucleic acid and protein interactions

Aromatic capping surprisingly stabilizes furan moieties in peptides against acidic degradation

How to Spoil the Taste of Insect Prey? A Novel Feeding Deterrent against Ants Released by Larvae of the Alder Leaf Beetle, Agelastica alni

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