Experiments on the lysine and aspartic acid residues in bacitracin A

Lockhart, I. M.; Abraham, E. P.

doi:10.1042/bj0620645

Cited by 20 publications

(13 citation statements)

References 14 publications

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“…The residue was dissolved in water and evaporation repeated twice to remove HCI. The pattern obtained when this hydrolysate was subjected to electrophoresis on paper in 0-05M-collidine acetate (pH 7) was similar to that obtained earlier with a partial hydrolysate of bacitracin A (Lockhart & Abraham, 1956). Partial hydrolysate of c-aspartyl-lysine.…”

Section: Methodssupporting

confidence: 80%

“…The DNP derivative of E-(aminosuccinyl)-lysine yielded DNP-aspartic acid and a-DNP-lysine on hydrolysis and also an ether-soluble product which remained at the origin on paper chromatograms (Blackburn & Lowther, 1951) and showed a bright-green fluorescence in ultraviolet light (365 m,u). A similar product was reported by Lockhart & Abraham (1956) to be formed on reaction of the 'Asp. Lys' from bacitracin A with 1 -fluoro-2:4-dinitrobenzene.…”

Section: I95j8supporting

confidence: 80%

“…Part of the evidence for this sequence is based on the analysis of two products of hydrolysis of bacitracin A which are strikingly resistant to acid. One of these products appeared to consist only of lysine and aspartic acid residues and the other of lysine, aspartic acid and isoleucine residues (Lockhart & Abraham, 1956). Nevertheless, both products were more basic than was to be expected if they were peptides containing two amino groups and two carboxyl groups.…”

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confidence: 91%

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Formation of ∈-(aminosuccinyl)-lysine from ∈-aspartyl-lysine from bacitracin A, and from the cell walls of lactobacilli

Swallow

Abraham

1958

Biochemical Journal

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Section: Methodssupporting

confidence: 80%

Section: I95j8supporting

confidence: 80%

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confidence: 91%

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Formation of ∈-(aminosuccinyl)-lysine from ∈-aspartyl-lysine from bacitracin A, and from the cell walls of lactobacilli

Swallow

Abraham

1958

Biochemical Journal

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“…The components of 6,7,10,ll,12,13,15 and 16,andpeaksNo. 24,25,26,27,28,29 and 31 Comparison of the MICsand the proposed structures of the minor componentssuggest that the location of the valine affects the activity of each component in the following decreasing order: TV-terminus, the seven membered peptide ring, and the side chain peptide moiety. Because this order is related to the elution order of the minor components on the HPLC, the activity may depend on the hydrophobicity of the respective component.…”

Section: Confirmation Of Proposed Structures By Lc/ms and Ms/msmentioning

confidence: 99%

“…7,10,ll,12,13,15,16,24,25,26,27,28,29and 31 as indicated in Fig. 1 Table 1 were considered to be all D-alloisoleucines derived from TV-terminal L -isoleucines.…”

Section: Determination Of Minimal Inhibition Concentrationmentioning

confidence: 99%

Total Structures and Antimicrobial Activity of Bacitracin Minor Components.

et al. 1995

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Total structures of 13 minor components of bacitracin (BC) were proposed, and their antimicrobial activities were investigated. The components of BCincluding bacitracins A (BC-A) and F (BC-F) were isolated by preparative HPLCand were hydrolyzed under acidic conditions.The resulting amino acids were derivatized with l-fluoro-2,4-dinitrophenyl-5-L-alanineamide and were separated by HPLCto determine their absolute configurations. It was found that the TV-terminal amino acids of BC-Aand its related components were epimerized during the hydrolysis to yield their enantiomers. The formation of these artifactual amino acids suggests that our previously proposed structures of the BCminor componentsare incorrect; therefore, the structures were corrected based on these results. The structures of the BCminor componentswere the same as that of BCs-A and -F except that one to three of the L-isoleucines, including the TV-terminal one, were replaced by L-valines. These structures were confirmed by tandem mass spectrometry under fast atom bombardment (FAB) conditions and Frit-FAB liquid chromatography/mass spectrometry. Based on the UVspectra of the BC components determined by photodiode array detection-HPLC analysis, a new systematic nomenclature was proposed for the minor components. The isolated components were also used for the determination of their minimal inhibition concentrations and it was found that BC-Ais 2~8 times more potent than the other minor componentsagainst strains of Micrococcus luteus and Staphylocoecusaureus.

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Synthesen in der Polymyxin‐Reihe. 6. Mitteilung. Versuch zur Synthese des cyclischen Decapeptides 7α über ein lineares Decapeptid

Studer

Vogler

1962

Helvetica Chimica Acta

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Volumen XLV, Fasciculus 111 (1962) -No. 96-97 819 enthalt demnach ca. 32% ( + )-Epigriseofulvin und ca. 68% ( + )-Griseofulvin. Aktivitat 4,31 . l o 5 ipm/mM, entsprechend dem Austausch von 1,048 Aquivalenten Methoxyl. Zur Lokalisierung der Aktivitat werden 131 mg des obigen Gemisches in 0,65 ml Eisessig und 0,13 ml 2~ Schwefelsaure bei ca. 98" wahrend 11/, h stehengelassen. Darauf wird im Eisschrank abgekuhlt, die ausgefallene Griseofulvinsaure abgenutscht und ausgiebig mit Methanol und Ather gewaschen. Das kristalline Produkt (73 mg) wird in Methanol gelost und mit Diazomethan verathert. Der feste Ruckstand wird im Hochvakuum bei ca. 170" destilliert. Man erhalt eine glasige Masse, die nach Diinnschichtchromatogramm aus (+ )-Griseofulvin und ( + )-Isogriseofulvin sowie deren Epimeren besteht.

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Experiments on the lysine and aspartic acid residues in bacitracin A

Cited by 20 publications

References 14 publications

Formation of ∈-(aminosuccinyl)-lysine from ∈-aspartyl-lysine from bacitracin A, and from the cell walls of lactobacilli

Formation of ∈-(aminosuccinyl)-lysine from ∈-aspartyl-lysine from bacitracin A, and from the cell walls of lactobacilli

Total Structures and Antimicrobial Activity of Bacitracin Minor Components.

Synthesen in der Polymyxin‐Reihe. 6. Mitteilung. Versuch zur Synthese des cyclischen Decapeptides 7α über ein lineares Decapeptid

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