A crystalline, toxic, peptide metabolite ofTrichoderma spp. isolated from soil

Brewer, D.; Hanson, A. W.; Shaw, I. M.; Taylor, A.; Jones, Graham A.

doi:10.1007/bf01964306

Cited by 6 publications

(6 citation statements)

References 12 publications

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“…The values given in Table 2 for the inhibition of cellulolysis by alamethicins and zervamicins refer to concentrations that resulted in no i observable digestion of the paper in 7 d. Control cultures grown under the same conditions without antibiotics had completely digested the paper in 48 h. All of the antibiotics had inhibitory effects at 25% of the concentrations given in Table 2. During the course of this work, samples of alamethicins containing different proportions of the component antibiotics (Brewer et al 1979) have been examined, but the results were very similar to those given in Table 2. Unfortunately, only small quantities of zervamicins IIa and IIb, which differ only in the substitution of a 2-ethylalanine residue for a 2methylalanine, were available, but the two-fold difference in activity seems to be reproducible.…”

Section: N H I B I T I O N Of C E L L U L O L Y S I S B Y a L A M Ementioning

confidence: 71%

“…Our earlier report (Brewer et al 1979) of the inhibition by alamethicins of the production of volatile fatty acids by rumen bacteria has been disputed (Bruckner & Graf 1983). It seems likely that these discrepant results are due to differences in both species and numbers of protozoa and bacteria used in the experiments reported, because it is known (Hungate 1966) that this population depends on the diet of the donor animal.…”

Section: Discussionmentioning

confidence: 96%

“…1941) that the size of the migrating particle is large (Stearn et al 1940). It is known that in the crystal (Brewer et al 1979;Fox & Richards 1982) alamethicin molecules are associated and it has been suggested that the mode of this association accounts for their remarkable effects on the conductivity of membranes (Hanke et al 1983). Practically, an important consequence of this association is the requirement for precise control of diffusion time and temperature in any biological or quasibiological system under investigation.…”

Section: Discussionmentioning

confidence: 99%

“…A systematic investigation of the biological activity of these peptaibols was therefore initiated and the results of this work are reported. A preliminary account of these investigations has been published (Brewer et al 1979).…”

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confidence: 99%

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The antibacterial activity of alamethicins and zervamicins

Jen

Jones

Brewer

et al. 1987

Journal of Applied Bacteriology

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Consistent results were obtained in biological assays of alamethicins on agar gels only when the antibiotics were allowed to diffuse under strictly defined conditions of temperature and time before inoculation. In liquid culture obligatory anaerobic rumen bacteria were sensitive to these antibiotics and in certain cases their ability to produce volatile fatty acids was reduced. Among the bacteria examined there was a 1000-fold difference in their sensitivity. Modifications of the structure of the peptaibol, e.g. substitution of an alanine residue for a 2-methylalanine residue resulted in ca two-fold changes in activity.

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Section: N H I B I T I O N Of C E L L U L O L Y S I S B Y a L A M Ementioning

confidence: 71%

Section: Discussionmentioning

confidence: 96%

Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

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The antibacterial activity of alamethicins and zervamicins

Jen

Jones

Brewer

et al. 1987

Journal of Applied Bacteriology

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“…1 l), the suzukacillins (6), and the alamethicins (12) are very complex mixtures and that the proportions of the individual components of the mixture depend on the conditions of growth of the producing fungus. These facts and the worldwide interest in the physiological properties of these materials have led to extraordinary synthetic efforts to obtain a single entity by synthesis (13)(14)(15)(16)(17).…”

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confidence: 99%

The chemistry of peptides related to metabolites of Trichoderma spp. 2. An improved method of characterization of peptides of 2-methylalanine

Shaw¹,

Taylor²

1986

Can. J. Chem.

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I. M. SHAW and A. TAYLOR. Can. J. Chem. 64, 164 (1986).4-Chlorobenzoylazide reacts with amino acid and peptide esters to give the 4-chlorobenzoyl derivatives in 60-90% yield, at room temperature, without measurable racemization. The reaction also proceeds smoothly with hindered amines such as methyl 2-methylalaninate and with secondary amines, e.g. methyl L-prolyl-L-valinate. Ten examples of the reaction are reported with peptides, synthesized for the purpose, that might be accessible from hydrolysates of the numerous fungal metabolites now known, which contain a high proportion of 2-methylalanine. The derivatives of di-, tri-, tetra-, and pentapeptides were highly crystalline, with sharp melting points, and could be detected and integrated in the effluent from chromatography columns at about the 10-ng level. This simple method of derivatization might be usefully applied to the resolution of discrepancies in the physical properties of ostensibly the same 2-methylalanyl peptide prepared in different laboratories.I. M. SHAW et A. TAYLOR. Can. J. Chem. 64, 164 (1986). L'azoture du chloro-4 benzoyle rkagit avec les esters d'acides aminks et de peptides, B la tempCrature ambiante, pour conduire aux dCrivks chloro-4 benzoylks avec des rendements de 60 i i 90% et sans rackmisation mesurable. La rkaction se produit aussi facilement avec des amines encombrkes, comme le mCthyl-2 alaninate de mkthyle, et avec des amines secondaires, comme le L-prolyl-L-valinate de mkthyle. On rapporte dix exemples de la reaction avec des peptides, synthCtisCs B cette fin, qui peuvent se retrouver dans les hydrolysats de plusieurs mktabolites de champignons qui sont maintenant connus pour contenir une grande proportion de mkthyl-2 alanine. Les dkrivCs des di-, tri-, tetra-et pentapeptides sont trks cristallins, ils ont des points de fusion bien dkfinis et ils peuvent itre dCtectks et intCgrCs en chromatographie a des niveaux de 10 ng. Cette simple mCthode de prkparer un dkrivC peut itre appliquke utilement B la rksolution des diffkrences dans les propriktks physiques de peptides de la methyl-2 alanine qui semblent les mimes, mais qui ont Ctk prCparCs dans des laboratoires diffkrents.

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