600 MHz proton magnetic resonance studies of natural and synthetic alamethicin

Davis, D.G.; Gisin, B. F.

doi:10.1016/0014-5793(81)80516-9

Cited by 18 publications

(8 citation statements)

References 11 publications

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“…Molecular Formula. The 13C NMR spectrum of TA IIIc exhibits 91 carbon atoms (Figure 2); 22 of them are carbonyl carbons, in agreement with previous results: 1 acetyl group and 18 amino acids, including 3 Gin. The aromatic carbons of the tryptophanol can be clearly recognized in the spectrum.…”

Section: Discussionsupporting

confidence: 91%

Structure of trichorzianine A IIIc, an antifungal peptide from Trichoderma harzianum

Bodo¹,

Rebuffat²,

Hajji³

et al. 1985

J. Am. Chem. Soc.

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Section: Discussionsupporting

confidence: 91%

Structure of trichorzianine A IIIc, an antifungal peptide from Trichoderma harzianum

Bodo¹,

Rebuffat²,

Hajji³

et al. 1985

J. Am. Chem. Soc.

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“…Most recently, the two dimensional absorption-mode homonuclear cross-polarization spectrum of alamethicin has been reported (21). The connectivities among residues observed basically agree with the earlier NMR spectral assignments of Davis & Gisin (22) and Banerjee·et al (3,4).…”

Section: Alamethicin An Antibiotic Peptidesupporting

confidence: 83%

“…Much of the conformational information concerning antibiotic pep tides that interact with membranes has come from physical studies such as NMR experiments (22,34). For example, a detailed NMR relaxation study of alamethicin (3), an antibiotic eicosapeptide, at 500 MHz suggested that in methanol the peptide forms a dimer in which residues 3-9 form an a-helix and amino acids 10-14 are in an open non-hydrogen-bonded conformation.…”

Section: Alamethicin An Antibiotic Peptidementioning

confidence: 99%

Peptides With Affinity for Membranes

Et¹,

Fj²

1987

Annu. Rev. Biophys. Biophys. Chem.

187

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“…The complexity of the I3C NMR spectra increased particularly in the aliphatic region of the alarnethicin-(14-20) and - (12)(13)(14)(15)(16)(17)(18)(19)(20) However, satisfying assignments (Table 2) together with the signals of Phl-C-2, -6 and Phl-C-4 (characteristic difference of 2 ppm as discussed above). All expected signals of protecting groups of the nonapeptide segment 3 were found ( Table 2).…”

Section: Spectra Of Hepta-to Decapeptidesmentioning

confidence: 79%

¹³C NMR Spectroscopic Control of the Synthesis of Alamethicin F 30 and its Segments

Schmitt

Jung

1985

Liebigs Ann. Chem.

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All segments built up for the total synthesis of the a-helical antibiotic alamethicin F 30 (1) were investigated by l3C NMR spectroscopy of rnethanolic solutions. With a few exceptions the signals were unequivocally assignable by comparison with spectra of related peptides, by coupled spectra and J-modulated spin-echo experiments. For the first time a synthetic and highly pure alamethicin F 30 preparation could be studied by I3C NMR spectroscopy at 100.6 MHz. All results were in full agreement with the synthesized intermediates and the final product, and with their conformations as derived from circular dichroism and X-ray analysis. Partially there is a striking retention of conformation from smaller to larger segments. '3GNMR-Spektroskopishe Synthesekontrolle von Alamethicin F 30 und seinen SegmentenAlle zur Totalsynthese des Alamethicin F 30 (1) aufgebauten Segmente wurden mittels 13C-NMRSpektroskopie methanolischer LXisungen untersucht. Mit wenigen Ausnahmen waren alle Signale eindeutig durch Vergleich mit anderen Peptidspektren, gekoppelte Spektren und vor allem durch J-modulierte Spin-Echo-Experimente zuzuordnen. Erstmals konnte ein synthetisches und hochreines Alamethicin-Praparat durch '3C-NMR-Spektroskopie bei 100.6 MHz untersucht werden. Alle Resultate sind in voller Ubereinstirnmung mit den synthetisierten Zwischenstufen und dem Endprodukt sowie deren Konformationen, die aus dem Circulardichroismus und aus Rontgenstrukturanalysen entnommen werden konnen. Es wurde eine zum Teil iiberraschende Erhaltung der Konformation beim Ubergang von kleineren zu groReren Segmenten beobachtet.Our total synthesis of the linear eicosapeptide antibiotic alamethicin F 30 (1) has been described in the preceding publication'). In order to support the common analyses used for control of this peptide synthesis we report in the following a complete I3C NMR study of all segments and the final product alamethicin F 30 (1).The results are also interpreted in terms of conformational assignments, particulary for those segments where X-ray analyses or CD spectra were available.The first I3C NMR study of natural alamethicin was reported in 1974, and it included already "C NMR longitudinal relaxation time (q) measurementsz), an interpretation in terms of a-helical conformationz), and data of some dipeptide derivatives. In the following years a considerable variety of synthetic Aib-containing oligo-and polypeptides were measured by 13C NMR3-m.These spectroscopic studies dealt with the con formational development during stepwise synthesis of sequential oligomers bound to the polyoxyethylene and they included the N-terminal natural undecapeptide sequence of alamethicin'). 13C NMR was of particular value for the conformational assignments of @-helices such as the undecapeptide Boc-Ala-(Aib-Ala),-Glu-0 VCH Verlagsgesellschaft mbH, D-6940 Weinheim, 1985

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600 MHz proton magnetic resonance studies of natural and synthetic alamethicin

Cited by 18 publications

References 11 publications

Structure of trichorzianine A IIIc, an antifungal peptide from Trichoderma harzianum

Structure of trichorzianine A IIIc, an antifungal peptide from Trichoderma harzianum

Peptides With Affinity for Membranes

¹³C NMR Spectroscopic Control of the Synthesis of Alamethicin F 30 and its Segments

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600 MHz proton magnetic resonance studies of natural and synthetic alamethicin

Cited by 18 publications

References 11 publications

Structure of trichorzianine A IIIc, an antifungal peptide from Trichoderma harzianum

Structure of trichorzianine A IIIc, an antifungal peptide from Trichoderma harzianum

Peptides With Affinity for Membranes

13C NMR Spectroscopic Control of the Synthesis of Alamethicin F 30 and its Segments

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Product

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¹³C NMR Spectroscopic Control of the Synthesis of Alamethicin F 30 and its Segments