Synthesen in der Polymyxinreihe. 11. Mitteilung. Die Synthese von Circulin A

Studer, R. O.; Lergier, W.; Vogler, K.

doi:10.1002/hlca.19660490218

Cited by 16 publications

(5 citation statements)

References 24 publications

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“…96,97 This observation can be potentially construed in terms of the differences in the lipid A fatty acyl chain composition across these bacteria which in turn confers different OM properties. 95,98 In their more recent work Sakura et al 94 described a comprehensive series of N R analogues were derived by acylation of the tetrakis(N γ -Troc)-PMB or colistin nonapeptides with various hydrophobic acids with aliphatic or hydrophobic ring structures (64)(65)(66)(67)(68)(69)(70)(71)(72)(73)(74)(75)(76)(77)(78)(79). The N R analogues were tested for LPS binding affinity and antimicrobial activity against E. coli, S. enterica serovar Typhimurium, and P. aeruginosa.…”

Section: Sar Of Polymyxinsmentioning

confidence: 99%

“…Total synthesis of a polymyxin was first achieved by Vogler et al − using a solution-phase segment condensation approach. However, the efficient generation of analogues has ultimately depended upon the development of solid-phase synthetic methods and specifically the development of orthogonal protection strategies around the l -Dab residues.…”

Section: Complete Synthesis Of Polymyxinsmentioning

confidence: 99%

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Structure−Activity Relationships of Polymyxin Antibiotics

Velkov

Thompson²,

Nation³

et al. 2009

J. Med. Chem.

642

776

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Section: Sar Of Polymyxinsmentioning

confidence: 99%

Section: Complete Synthesis Of Polymyxinsmentioning

confidence: 99%

Structure−Activity Relationships of Polymyxin Antibiotics

Velkov

Thompson²,

Nation³

et al. 2009

J. Med. Chem.

642

776

View full text Add to dashboard Cite

“…1, these peptides differ only in the amino acid residues at positions three, six, and seven, and in the nature of the amino-terminal fatty acid. The structures of polymyxin Bl (VOGLER et al, 1964) and of circulin A (STUDER et al, 1966) have been confirmed by chemical synthesis. Previous structures proposed for these peptides (BISERTE and DAUTREVAUX, 1957;SUZUKI, 1957;DAUTREVAUX and BISERTE, 1961;KOFFLER and KOBAYASHI, 1959) appear to be incorrect.…”

Section: Polymyxins Henry Paulusmentioning

confidence: 79%

Biosynthesis

1967

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All rights, especially that of translation into f oreign 1anguages, reserved. It is also forbidden to reproduce this book, either who1e or in part, by photomechanical means (photostat, microfilm and/or microcard) or by other procedure without written pennission from Springcr-Vcrlag Berlin Heide1bCig GmbH. DedicationFor most areas of scientific pursuit, there is usually that rare investigator who has the imagination to conceive ideas, who has faith in his visions, and who has the ability to critically test his concepts in the laboratory. Almost invariably, this scientist also inspires younger men to enthusiastically enter into his research program. To him should go the accolades and the recognitions of the esteem in which he is held. As only a small part of this esteem, we wish to dedicate these books to Professor SELMAN A. W AKSMAN in appreciation of his leadership and contributions in all facets of antibiotic research. PrefaceThe idea for publishing these books on the mechanism of action and on the biosynthesis of antibiotics was born of frustration in our attempts to keep abreast of the literature. Gone were the years when we were able to keep a bibliography on antibiotics and feel confident that we could find everything that was being published on this sUbject. These fields of investigation were moving forward so rapidly and were encompassing so wide a range of specialized areas in microbiology and chemistry that it was almost impossible to keep abreast of developments. In our naivete and enthusiasm, however, we were unaware that we were toying with an idea that might enmesh us, that we were creating an entity with a life of its own, that we were letting loose a Golom who instead of being our servant would be our master.That we set up ideals for these books is obvious; they would be current guides to developments and information in the areas of mechanism of action and biosynthesis of antibiotics. For almost every subject, we wished to enlist the aid of an investigator who himself had played a part in determining the nature of the phenomena that were being discussed. One concept for the books was that they include only antibiotics for which a definitive, well-documented mechanism of action or biosynthetic pathway was known. Yet, such an approach would not entirely serve the purpose we projected, for it would not encompass all of the information available in these fields of antibiotic investigations and blind searches for the original literature would still have to be made. We therefore chose to include any and all antibiotics about which some pertinent information had been published. It was obvious even at the start that such a compilation, integration, and analysis of information could never be complete unless scientific investigations ceased at the moment the last manuscript was submitted-an end that was neither desirable nor possible. An addendum was therefore included at the end of the volume and left open for the addition of new information until the last pages of the regular articles had been printed.The...

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“…Beim Circulin A ist durch erneute Strukturuntersuchungen [5] und insbesondere durch die von VOGLER [6] durchgefuhrte Totalsynthese nachgewiesen worden, da13 es kein einfaches cyclisches Dekapeptid darstellt, sondern vielmehr ein ,,sigmoides" Peptid mit einem den Polymyxinen entsprechenden Aufbau.…”

Section: Lys(pht)-lys(z)-thr-lys(z)-thr-lys(z)-lys(z)-d-leu-omeunclassified

“…C 62,29 H 6,21 N 9,78 Nat e r t. b) Nach der Methode der gemischten Anhydride 2,4 g (6,5 mMol) Boc-Lys(Z)-OH werden in 15 ml Tetrahydrofuran gelost iind mit 0,99 g Triathylamin versetzt. Bei -15' tropft man dazu unter Ruhren 0,66 ml (6,6 mMol) Chlorkohlensauremethyylester und gibt nach 10 Minuten eine auf -15' vorgekiihlte Losung yon 1,77 g Threoninmethylester in 10 ml Tetrahydrofuran zu. Man belaat das Gemisch eine Stunde bei -10" und anschlieBend 48 Stunden bei Raumtemperatur.…”

Section: Lys(pht)-lys(z)-thr-lys(z)-thr-lys(z)-lys(z)-d-leu-omeunclassified

Peptide, XII. Synthese eines linearen Dekapeptids mit potentieller modifizierter Circulin‐Sequenz

1969

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Durch Umsetzung von Boc‐Lys(Z)‐Thr‐Lys(Z)‐Thr‐N3 [3] mit Lys(Z)‐Lys(Z)‐D‐Leu OMe [1] wird das Heptapeptid Boc‐Lys(Z)‐Thr‐Lys(Z)‐Thr‐Lys(Z)‐Lys(Z)‐D‐Leu‐OMe 13 erhalten. Nach Abspaltung der Boc‐Gruppe wird es mit dem Tripeptid‐Derivat Boc‐Ile‐Lys(Z)‐Lys(Pht)‐ONP 7 zum vollständig geschützten Dekapeptid Boc‐Ile‐Lys(Z)‐Lys(Pht)‐Lys(Z)‐Thr‐Lys(Z)‐Thr‐Lys (Z)‐Lys(Z)‐D‐Leu‐OMe 14 umgesetzt.

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Synthesen in der Polymyxinreihe. 11. Mitteilung. Die Synthese von Circulin A

Cited by 16 publications

References 24 publications

Structure−Activity Relationships of Polymyxin Antibiotics

Structure−Activity Relationships of Polymyxin Antibiotics

Biosynthesis

Peptide, XII. Synthese eines linearen Dekapeptids mit potentieller modifizierter Circulin‐Sequenz

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