Determination of α-alkyl-α-amino acids and α-amino alcohols by chiral-phase capillary gas chromatography and reversed-phase high-performance liquid chromatography

Brückner, Hans; Bosch, I.; Graser, Theodor; Fürst, Peter

doi:10.1016/s0021-9673(01)94145-7

Cited by 29 publications

(6 citation statements)

References 45 publications

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“…Separation of dl-Iva and dl-Pip, analyzed as N-trifluoroacyl amino acid propyl esters on Chirasil-l-Val TM (N-propionyll-valine-tert-butylamide polysiloxane), is not always satisfactory, as it depends both on the age and quality of the capillary columns provided by various manufacturers. However, Iva enantiomers can be resolved on Chirasil-l-Val TM after conversion into Nacetylisovaline propyl esters [63]. Instead of Chirasil-l-Val TM , a Lipodex TM E column, representing a functionalized g-cyclodextrine, can be used providing excellent resolution of Iva and Pro enantiomers [64].…”

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confidence: 99%

New Sequences, Constituents, and Producers of Peptaibiotics: An Updated Review

Degenkolb

Kirschbaum

Brückner

2007

Chemistry & Biodiversity

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To date, 18 genera of imperfect and ascomycetous fungi have been recognized to produce ca. 700 individual sequences of peptaibiotics. These are linear polypeptide antibiotics which i) have a molecular weight between 500 and 2,200 Dalton, thus containing 5-21 residues; ii) show a high content of alpha-aminoisobutyric acid; iii) are characterized by the presence of other nonproteinogenic amino acids and/or lipoamino acids; iv) possess an acylated N-terminus, and v) have a C-terminal residue that, in most of them, consists of a free or acetylated amide-bonded 1,2-amino alcohol, but might also be an amine, amide, free amino acid, 2,5-dioxopiperazine, or sugar alcohol. From April 2003 until present, ca. 300 new individual sequences of peptaibiotics have been published in the literature, but most of them have not yet been included in databases. To summarize these new sequences and novel constituents, as well as to introduce fungal species hitherto unknown as producers of peptaibiotics, the relevant literature is reviewed. Furthermore, ecophysiological and taxonomic aspects of the producing fungi are discussed.

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confidence: 99%

New Sequences, Constituents, and Producers of Peptaibiotics: An Updated Review

Degenkolb

Kirschbaum

Brückner

2007

Chemistry & Biodiversity

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“…Because a huge number of new Aib-positive species and strains of Trichoderma has been detected [82] [83], this method was subsequently broadened, and both GC-FID and GC/MS were used for screening of Stilbella, Emericellopsis, Gliocladium, Trichoderma, and Hypocrea [84 -86]. For resolution of dl-Iva on ChirasilVal TM , conversion into N-acetyl-isovaline-1-propyl esters was found to be superior [87]. HPLC Analysis after precolumn derivatization of the total hydrolysate with o-phthaldialdehyde-3-mercaptopropionic acid (OPA/MPA) was introduced at the same time [85]; and subsequently different chiral variations of Marfeys reagent were used for HPLC analysis of amino acids [88 -90].…”

Section: 3mentioning

confidence: 99%

Peptaibiomics: Towards a Myriad of Bioactive Peptides Containing C^α‐Dialkylamino Acids?

Degenkolb

Brückner

2008

Chemistry & Biodiversity

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Fungi are generally regarded as a literally infinite resource of bioactive secondary metabolites displaying remarkable structural diversity. Research on a particular group of linear and cyclic peptide antibiotics comprehensively named peptaibiotics--as result of the abundance of the non-proteinogenic C(alpha)-dialkylated alpha-amino acids alpha-aminoisobutyric acid (Aib) and isovaline (Iva)--has been started 50 years ago. These peptides have gained constantly increasing interest because of their unique bioactivities and conformations. This review, reflecting the history of peptaibiotic research from 1958 to 2008, is focussed on introducing both the structural diversity and natural microheterogeneity of the peptaibiotics, as well as the biodiversity of their fungal producers. Recently introduced state-of-the-art methods for rapid screening and sequencing of peptaibiotics, such as peptaibiomics and intact-cell MALDI-TOF mass spectrometry, are discussed. Finally, future prospects in peptaibiotic research are presented. Owing to the ubiquity and biodiversity of the fungal producers in the biosphere, the discovery of a myriad of peptaibiotics within the next decade is predicted.

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“…The requirement of sufficient stability of the ternary copper complex requires five-membered ring formation and compounds such as a-amino acids and a-hydroxy acids are the most suitable. Literature survey reveals separation of a large number of racemates on these layers (Günther et al, 1985;Mack et al, 1988;Mack and Hauck, 1989;Gont and Neundorf, 1987;Brückner 1987;Brückner et al, 1987;Toth et al, 1990;Pyka, 1993;Golkiewicz and Polak, 1994).…”

Section: Enantiomersmentioning

confidence: 99%

Separation of amino acids, their derivatives and enantiomers by impregnated TLC

Bhushan

Martens

2001

Biomedical Chromatography

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The present state of TLC with respect to separation of amino acids, their different derivatives and their enantiomers by the technique of impregnation is discussed. The main approaches to impregnation viz. mixing of a suitable reagent with the adsorbent prior to plate-making, immersion of the untreated plate in the solution of impregnating reagent prior to development, and modification of the adsorbent, have been identified and discussed for each class of these compounds. The role of impregnation in resolving enantiomers or in improving the separation of mixtures of amino acids or their derivatives in terms of ion pairing, complex formation, ligand exchange or other steric interactions has been elaborated in each category.

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Determination of α-alkyl-α-amino acids and α-amino alcohols by chiral-phase capillary gas chromatography and reversed-phase high-performance liquid chromatography

Cited by 29 publications

References 45 publications

New Sequences, Constituents, and Producers of Peptaibiotics: An Updated Review

New Sequences, Constituents, and Producers of Peptaibiotics: An Updated Review

Peptaibiomics: Towards a Myriad of Bioactive Peptides Containing C^α‐Dialkylamino Acids?

Separation of amino acids, their derivatives and enantiomers by impregnated TLC

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Determination of α-alkyl-α-amino acids and α-amino alcohols by chiral-phase capillary gas chromatography and reversed-phase high-performance liquid chromatography

Cited by 29 publications

References 45 publications

New Sequences, Constituents, and Producers of Peptaibiotics: An Updated Review

New Sequences, Constituents, and Producers of Peptaibiotics: An Updated Review

Peptaibiomics: Towards a Myriad of Bioactive Peptides Containing Cα‐Dialkylamino Acids?

Separation of amino acids, their derivatives and enantiomers by impregnated TLC

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Peptaibiomics: Towards a Myriad of Bioactive Peptides Containing C^α‐Dialkylamino Acids?