1985
DOI: 10.1002/jlac.198519850210
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Total Synthesis of the α‐Helical Eicosapeptide Antibiotic Alamethicin

Abstract: The voltage-dependent membrane pore-forming polypeptide antibiotic alamethicin F 30 (Ac-Aib-Pro-Aib-Ala-Aib-Ala-Gln-Aib-Val-Aib-Gly-Leu-Aib-Pro-Val-Aib-Aib-Glu-Gln-Phl, 1) was synthesiied by segment condensations. It was obtained free of racemate (<0.8% o-components) via the segments 2-11 (4a) and 12-20 (3a) using the dicyclohexylcarbodiimide/l-hydroxybenzotriazole and the mixed anhydride methods. The intermediates were unequivocally characterized by chromatographic and physical methods including I3C NMR, circ… Show more

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Cited by 76 publications
(25 citation statements)
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References 52 publications
(7 reference statements)
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“…All were homogeneous on reverse phase partition chromatography and the retention volumes measured are given in crystalline peptides were hydrated, the water of hydration being tenaciously held. This unexpected phenomenon was reported recently for an analogous compound (14).…”
Section: [Traduit Par Le Journal]supporting
confidence: 82%
See 1 more Smart Citation
“…All were homogeneous on reverse phase partition chromatography and the retention volumes measured are given in crystalline peptides were hydrated, the water of hydration being tenaciously held. This unexpected phenomenon was reported recently for an analogous compound (14).…”
Section: [Traduit Par Le Journal]supporting
confidence: 82%
“…The data in Tables 1 and 2 (8) is 23, but for the pentapeptide with the C-terminus 2-methylalanyl-2-methylalanylglutamate (6), the ratio is 3. The NH group between two 2-methylalanine residues is not readily exchanged (14), and in our hands cannot be methylated except under forcing conditions when C-methylation also occurs. The data in Table 1 therefore support the hypothesis that the probability of dehydration depends on the steric hindrance of the 2-methylalanyl NH group.…”
Section: [Traduit Par Le Journal]mentioning
confidence: 67%
“…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). The results of these efforts in the alamethicin field have been symmarized by Schmidt and Jung (16), who show that the measurements of the physical properties of the synthetic products by the different groups fall outside normally accepted ranges of error.…”
mentioning
confidence: 99%
“…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). The results of these efforts in the alamethicin field have been symmarized by Schmidt and Jung (16), who show that the measurements of the physical properties of the synthetic products by the different groups fall outside normally accepted ranges of error. The structures of many of the intermediates in the syntheses have been established by detailed assignment of 'H and I3C nmr spectra (see e.g., ref.…”
mentioning
confidence: 99%
“…Diese Arbeit steht damit in der Nachfolge anderer Meilensteine der Peptid-Synthese, z. B. der Synthese des Membranporen bildenden Antibiotikums Alamethicin [10] und des DNA-Gyrase-Inhibitors Microcin. [11] Im Falle von Polytheonamid B (1) …”
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