PMID: 11606216Oct 19, 2001Paper

Partial [alphaMe]Aun scan of [l-Leu11-OMe]-trichogin GA IV, a membrane active synthetic precursor of the natural lipopeptaibol

The Journal of Peptide Research : Official Journal of the American Peptide Society
C PeggionQ B Broxterman

Abstract

We synthesized using solution-phase methods three analogs of [l-Leu11-OMe] trichogin GA IV, a membrane active synthetic precursor of the lipopeptaibol antibiotic in which the N-terminal n-octanoyl group and each of the three Aib residues in positions 1, 4 and 8 are replaced by an acetyl group and the lipophilic Calpha,alpha-disubstituted glycine l-(alphaMe)Aun, respectively [partial (alphaMe)Aun scan]. FT-IR absorption and CD analyses unequivocally show that the main three-dimensional structural features of [l-Leu11-OMe] trichogin GA IV are preserved in the analogs. Also, [l-Leu11-OMe] trichogin GA IV and the three Nalpha-acetylated l-(alphaMe)Aun analogs exhibit strictly comparable membrane-modifying properties. Taken together, these results strongly favor the conclusion that a shift of the long hydrocarbon moiety from the Nalpha-blocking group to the side-chain of the 1, 4 or 8 residue does not have any significant effect on the conformational properties or the membrane activity of [l-Leu11-OMe] trichogin GA IV and, by extension, of the natural lipopeptaibol.

References

Sep 1, 1991·Trends in Biochemical Sciences·C Toniolo, E Benedetti
Jan 1, 1980·CRC Critical Reviews in Biochemistry·C Toniolo
Dec 1, 1994·Nature Structural Biology·C TonioloD S Eggleston
Apr 1, 1999·Journal of Peptide Science : an Official Publication of the European Peptide Society·C PiazzaQ B Broxterman
Dec 3, 1999·European Journal of Biochemistry·R F EpandC Toniolo
Mar 22, 2000·The Journal of Peptide Research : Official Journal of the American Peptide Society·C PeggionC Toniolo
Feb 13, 2001·European Journal of Biochemistry·R F EpandC Toniolo
Feb 24, 2001·Chemistry : a European Journal·F FormaggioC Toniolo
Oct 2, 2001·Cellular and Molecular Life Sciences : CMLS·C TonioloR M Epand
Oct 2, 2001·Cellular and Molecular Life Sciences : CMLS·C Boucheix, E Rubinstein
Oct 19, 2001·The Journal of Peptide Research : Official Journal of the American Peptide Society·C PeggionQ B Broxterman
Jan 1, 1991·Biotechnology Advances·E A Falch

❮ Previous
Next ❯

Citations

Nov 15, 2011·Analytical and Bioanalytical Chemistry·L StellerR Salzer
Dec 9, 2003·Journal of Peptide Science : an Official Publication of the European Peptide Society·Cristina PeggionClaudio Toniolo
Sep 28, 2007·Natural Product Reports·Juliana F de S Daniel, Edson Rodrigues Filho
Dec 20, 2011·Organic & Biomolecular Chemistry·Marta De ZottiClaudio Toniolo
Oct 19, 2001·The Journal of Peptide Research : Official Journal of the American Peptide Society·C PeggionQ B Broxterman
Jun 17, 2020·Journal of Colloid and Interface Science·Sofie Fogh HedegaardHanne Mørck Nielsen
Nov 10, 2006·The Journal of Physical Chemistry. B·Emanuela GattoBasilio Pispisa

❮ Previous
Next ❯

Related Concepts

Related Feeds

ApoE, Lipids & Cholesterol

Serum cholesterol, triglycerides, apolipoprotein B (APOB)-containing lipoproteins (very low-density lipoprotein (VLDL), immediate-density lipoprotein (IDL), and low-density lipoprotein (LDL), lipoprotein A (LPA)) and the total cholesterol/high-density lipoprotein (HDL) cholesterol ratio are all connected in diseases. Here is the latest research.