Synthesis and conformational analysis of efrapeptins

Weigelt S, Huber T, Hofmann F, Jost M, Ritzefeld M, Luy B, Freudenberger C, Majer Z, Vass E, Greie J-C, Panella L, et al. (2012)
Chemistry - A European Journal 18(2): 478-487.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
Autor*in
Weigelt, Sven; Huber, Thomas; Hofmann, Frank; Jost, Micha; Ritzefeld, MarkusUniBi ; Luy, Burkhard; Freudenberger, Christoph; Majer, Zsuzsanna; Vass, Elemér; Greie, Jörg-Christian; Panella, Lavinia; Kaptein, Bernard
Alle
Abstract / Bemerkung
The efrapeptin family of peptide antibiotics produced by the fungus Tolypocladium niveum, and the neo-efrapeptins from the fungus Geotrichum candidumare inhibitors of F(1)-ATPase with promising antitumor, antimalaria, and insecticidal activity. They are rich in C(α)-dialkyl amino acids (Aib, Iva, Acc) and contain one β-alanine and several pipecolic acid residues. The C-terminus bears an unusual heterocyclic cationic cap. The efrapeptins C-G and three analogues of efrapeptin C were synthesized using α-azido carboxylic acids as masked amino acid derivatives. All compounds display inhibitory activity toward F(1)-ATPase. The conformation in solution of the peptides was investigated with electronic CD spectroscopy, FT-IR spectroscopy, and VCD spectroscopy. All efrapeptins and most efrapeptin analogues were shown to adopt helical conformations in solution. In the case of efrapeptin C, VCD spectra proved that a 3(10)-helix prevails. In addition, efrapeptin C was conformationally studied in detail with NMR and molecular modeling. Besides NOE distance restraints, residual dipolar couplings (RDC) observed upon partial alignment with stretched PDMS gels were used for the conformational analysis and confirmed the 3(10)-helical conformation.
Stichworte
Protein Structure; Secondary; Peptides/pharmacology; Peptides/chemistry; Peptides/chemical synthesis; Biomolecular; Nuclear Magnetic Resonance; Amino Acid Sequence; Adenosine Triphosphatases/antagonists & inhibitors; Anti-Bacterial Agents/chemistry; Anti-Bacterial Agents/chemical synthesis; Anti-Bacterial Agents/pharmacology; Circular Dichroism; Escherichia coli/enzymology; Hypocreales/chemistry; Models; Molecular Sequence Data; Molecular
Erscheinungsjahr
2012
Zeitschriftentitel
Chemistry - A European Journal
Band
18
Ausgabe
2
Seite(n)
478-487
ISSN
0947-6539
Page URI
https://pub.uni-bielefeld.de/record/2499381

Zitieren

Weigelt S, Huber T, Hofmann F, et al. Synthesis and conformational analysis of efrapeptins. Chemistry - A European Journal. 2012;18(2):478-487.
Weigelt, S., Huber, T., Hofmann, F., Jost, M., Ritzefeld, M., Luy, B., Freudenberger, C., et al. (2012). Synthesis and conformational analysis of efrapeptins. Chemistry - A European Journal, 18(2), 478-487. doi:10.1002/chem.201102134
Weigelt, Sven, Huber, Thomas, Hofmann, Frank, Jost, Micha, Ritzefeld, Markus, Luy, Burkhard, Freudenberger, Christoph, et al. 2012. “Synthesis and conformational analysis of efrapeptins”. Chemistry - A European Journal 18 (2): 478-487.
Weigelt, S., Huber, T., Hofmann, F., Jost, M., Ritzefeld, M., Luy, B., Freudenberger, C., Majer, Z., Vass, E., Greie, J. - C., et al. (2012). Synthesis and conformational analysis of efrapeptins. Chemistry - A European Journal 18, 478-487.
Weigelt, S., et al., 2012. Synthesis and conformational analysis of efrapeptins. Chemistry - A European Journal, 18(2), p 478-487.
S. Weigelt, et al., “Synthesis and conformational analysis of efrapeptins”, Chemistry - A European Journal, vol. 18, 2012, pp. 478-487.
Weigelt, S., Huber, T., Hofmann, F., Jost, M., Ritzefeld, M., Luy, B., Freudenberger, C., Majer, Z., Vass, E., Greie, J.-C., Panella, L., Kaptein, B., Broxterman, Q.B., Kessler, H., Altendorf, K., Hollósi, M., Sewald, N.: Synthesis and conformational analysis of efrapeptins. Chemistry - A European Journal. 18, 478-487 (2012).
Weigelt, Sven, Huber, Thomas, Hofmann, Frank, Jost, Micha, Ritzefeld, Markus, Luy, Burkhard, Freudenberger, Christoph, Majer, Zsuzsanna, Vass, Elemér, Greie, Jörg-Christian, Panella, Lavinia, Kaptein, Bernard, Broxterman, Quirinus B, Kessler, Horst, Altendorf, Karlheinz, Hollósi, Miklós, and Sewald, Norbert. “Synthesis and conformational analysis of efrapeptins”. Chemistry - A European Journal 18.2 (2012): 478-487.

16 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Expanding lysine industry: industrial biomanufacturing of lysine and its derivatives.
Cheng J, Chen P, Song A, Wang D, Wang Q., J Ind Microbiol Biotechnol 45(8), 2018
PMID: 29654382
RDC-enhanced structure calculation of a β-heptapeptide in methanol.
Rigling C, Ebert MO., Magn Reson Chem 55(7), 2017
PMID: 27976817
Functional expression of L-lysine α-oxidase from Scomber japonicus in Escherichia coli for one-pot synthesis of L-pipecolic acid from DL-lysine.
Tani Y, Miyake R, Yukami R, Dekishima Y, China H, Saito S, Kawabata H, Mihara H., Appl Microbiol Biotechnol 99(12), 2015
PMID: 25547835
4-Cyano-α-methyl-l-phenylalanine as a spectroscopic marker for the investigation of peptaibiotic-membrane interactions.
De Zotti M, Bobone S, Bortolotti A, Longo E, Biondi B, Peggion C, Formaggio F, Toniolo C, Dalla Bona A, Kaptein B, Stella L., Chem Biodivers 12(4), 2015
PMID: 25879497
Cruentaren A binds F1F0 ATP synthase to modulate the Hsp90 protein folding machinery.
Hall JA, Kusuma BR, Brandt GE, Blagg BS., ACS Chem Biol 9(4), 2014
PMID: 24450340
Solution synthesis, conformational analysis, and antimicrobial activity of three alamethicin F50/5 analogs bearing a trifluoroacetyl label.
De Zotti M, Ballano G, Jost M, Salnikov ES, Bechinger B, Oancea S, Crisma M, Toniolo C, Formaggio F., Chem Biodivers 11(8), 2014
PMID: 25146762
Probing spatial distribution of alignment by deuterium NMR imaging.
Trigo-Mouriño P, Merle C, Koos MR, Luy B, Gil RR., Chemistry 19(22), 2013
PMID: 23559417
Conformational properties of secondary amino acids: replacement of pipecolic acid by N-methyl-l-alanine in efrapeptin C.
Dutt Konar A, Vass E, Hollósi M, Majer Z, Grüber G, Frese K, Sewald N., Chem Biodivers 10(5), 2013
PMID: 23681735
Antimicrobial lipopeptaibol trichogin GA IV: role of the three Aib residues on conformation and bioactivity.
De Zotti M, Biondi B, Park Y, Hahm KS, Crisma M, Toniolo C, Formaggio F., Amino Acids 43(4), 2012
PMID: 22484376
Configuration verification via RDCs on the example of a tetra-substituted pyrrolidine ring.
Tzvetkova P, Luy B, Simova S., Magn Reson Chem 50 Suppl 1(), 2012
PMID: 23280666

64 References

Daten bereitgestellt von Europe PubMed Central.


AUTHOR UNKNOWN, 0

Gupta, J. Am. Chem. Soc. 113(), 1991

Gupta, J. Org. Chem. 57(), 1992
Structure at 2.8 A resolution of F1-ATPase from bovine heart mitochondria.
Abrahams JP, Leslie AG, Lutter R, Walker JE., Nature 370(6491), 1994
PMID: 8065448
The structure of bovine F1-ATPase complexed with the peptide antibiotic efrapeptin.
Abrahams JP, Buchanan SK, Van Raaij MJ, Fearnley IM, Leslie AG, Walker JE., Proc. Natl. Acad. Sci. U.S.A. 93(18), 1996
PMID: 8790345
Inhibition sites in F1-ATPase from bovine heart mitochondria.
Gledhill JR, Walker JE., Biochem. J. 386(Pt 3), 2005
PMID: 15537385
Spectroscopic and crystallographic studies of the mutant R416W give insight into the nucleotide binding traits of subunit B of the A1Ao ATP synthase.
Kumar A, Manimekalai MS, Balakrishna AM, Hunke C, Weigelt S, Sewald N, Gruber G., Proteins 75(4), 2009
PMID: 19003877
Antimalarial activities of peptide antibiotics isolated from fungi.
Nagaraj G, Uma MV, Shivayogi MS, Balaram H., Antimicrob. Agents Chemother. 45(1), 2001
PMID: 11120957
Inhibition of energy conservation reactions in chromatophores of Rhodospirillum rubrum by antibiotics.
Lucero H, Lescano WI, Vallejos RH., Arch. Biochem. Biophys. 186(1), 1978
PMID: 147053
Antibiotic inhibitors of mitochondrial ATP synthesis.
Lardy H, Reed P, Lin CH., Fed. Proc. 34(8), 1975
PMID: 124269
Inhibitors of the ATP synthethase system.
Linnett PE, Beechey RB., Meth. Enzymol. 55(), 1979
PMID: 156854
Properties of F1-ATPase from the uncD412 mutant of Escherichia coli.
Wise JG, Duncan TM, Latchney LR, Cox DN, Senior AE., Biochem. J. 215(2), 1983
PMID: 6228224
Resistance of thermophilic ATPase (TF1) to specific F1-atpase inhibitors including local anesthetics.
Saishu T, Kagawa Y, Shimizu R., Biochem. Biophys. Res. Commun. 112(3), 1983
PMID: 6221726

AUTHOR UNKNOWN, 0
F1F0-ATP synthase functions as a co-chaperone of Hsp90-substrate protein complexes.
Papathanassiu AE, MacDonald NJ, Bencsura A, Vu HA., Biochem. Biophys. Res. Commun. 345(1), 2006
PMID: 16682002
Mitochondrial inhibitors show preferential cytotoxicity to human pancreatic cancer PANC-1 cells under glucose-deprived conditions.
Momose I, Ohba S, Tatsuda D, Kawada M, Masuda T, Tsujiuchi G, Yamori T, Esumi H, Ikeda D., Biochem. Biophys. Res. Commun. 392(3), 2010
PMID: 20083087
Efrapeptins block exocytic but not endocytic trafficking of proteins.
Muroi M, Kaneko N, Suzuki K, Nishio T, Oku T, Sato T, Takatsuki A., Biochem. Biophys. Res. Commun. 227(3), 1996
PMID: 8886013
Highly N-methylated linear peptides produced by an atypical sponge-derived Acremonium sp.
Boot CM, Tenney K, Valeriote FA, Crews P., J. Nat. Prod. 69(1), 2006
PMID: 16441074
Efrapeptin J, a new down-regulator of the molecular chaperone GRP78 from a marine Tolypocladium sp.
Hayakawa Y, Hattori Y, Kawasaki T, Kanoh K, Adachi K, Shizuri Y, Shin-ya K., J. Antibiot. 61(6), 2008
PMID: 18667784

Krasnoff, J. Invertebr. Pathol. 58(), 1991

AUTHOR UNKNOWN, 0

Auvin-Guette, Tetrahedron Lett. 34(), 1993

Meldal, Tetrahedron Lett. 38(), 1997

Jost, Angew. Chem. 114(), 2002
The first total synthesis of efrapeptin C.
Jost M, Greie JC, Stemmer N, Wilking SD, Altendorf K, Sewald N., Angew. Chem. Int. Ed. Engl. 41(22), 2002
PMID: 12434358

AUTHOR UNKNOWN, 0

Kruizinga, J. Org. Chem. 53(), 1988

Kaptein, Tetrahedron: Asymmetry 4(), 1993
Alpha-azido acids for direct use in solid-phase peptide synthesis.
Tornoe CW, Davis P, Porreca F, Meldal M., J. Pept. Sci. 6(12), 2000
PMID: 11192239
The chemistry of amine-azide interconversion: catalytic diazotransfer and regioselective azide reduction.
Nyffeler PT, Liang CH, Koeller KM, Wong CH., J. Am. Chem. Soc. 124(36), 2002
PMID: 12207533

AUTHOR UNKNOWN, 0

Bartra, Tetrahedron Lett. 28(), 1987

Bartra, Tetrahedron 46(), 1990

Jost, Synthesis (), 2005
Synthesis, and structural and biological studies of efrapeptin C analogues.
Jost M, Weigelt S, Huber T, Majer Z, Greie JC, Altendorf K, Sewald N., Chem. Biodivers. 4(6), 2007
PMID: 17589859

Brückner, Angew. Chem. 91(), 1979
The sequences of the membrane-modifying peptide antibiotic trichotoxin A-40.
Bruckner H, Konig WA, Greiner M, Jung G., Angew. Chem. Int. Ed. Engl. 18(6), 1979
PMID: 111585

Caputo, Tetrahedron 51(), 1995

Weigelt, Synlett (), 2004
A microassay for ATPase.
Henkel RD, VandeBerg JL, Walsh RA., Anal. Biochem. 169(2), 1988
PMID: 2968057

Altendorf, Acta Physiol. Scand. 163(), 1998
Properties of F1-ATPase from the uncD412 mutant of Escherichia coli.
Wise JG, Duncan TM, Latchney LR, Cox DN, Senior AE., Biochem. J. 215(2), 1983
PMID: 6228224

Perczel, 1996
Characterization of beta-bend ribbon spiral forming peptides using electronic and vibrational CD.
Yoder G, Keiderling TA, Formaggio F, Crisma M, Toniolo C., Biopolymers 35(1), 1995
PMID: 7696550

Toniolo, J. Am. Chem. Soc. 118(), 1996
Vibrational spectroscopy and conformation of peptides, polypeptides, and proteins.
Krimm S, Bandekar J., Adv. Protein Chem. 38(), 1986
PMID: 3541539

Dwivedi, Biopolymers 23(), 1984

Keiderling, 2000

Yoder, J. Am. Chem. Soc. 119(), 1997
Structure refinement of cyclosporin A in chloroform by using RDCs measured in a stretched PDMS-gel.
Klages J, Neubauer C, Coles M, Kessler H, Luy B., Chembiochem 6(9), 2005
PMID: 16138307

Kummerlöwe, TrAC Trends Anal. Chem. 28(), 2009
Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®
Quellen

PMID: 22147615
PubMed | Europe PMC

Suchen in

Google Scholar